Your Turn: “I’m Jealous of His Sexual Past”

In a feature I call “Your Turn,” in which you, the readers, get to answer the question, I’m presenting the following letter without commentary from me:

I am a 19-year-old female and my boyfriend is 21. We have been committed to each other for 9 months (6 months of officially dating). We are a long distance couple and that, of course, is a huge problem for us — more so for him than for me.

I am a virgin and he has had 16 partners (me being the 17th when we finally do meet) and that really bugs me. Is that normal? Why do you think I feel that way? Also, he’s really into some kinky stuff such as video taping and what not.

I feel like nothing is going to be special for us because he’s already done almost everything and I’m not sexually experienced at all. Am I in the wrong to feel bad? I tell him I don’t want to do things he’s already done because I feel as if it won’t be special to him, but he promises me that it will be because he’s never had such immense, strong feelings for someone like me.

I just feel like my jealousy over his sexual past, which is constantly on the back of my mind, is going to get in the way. What I can do to get over this? – New to the Game


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  1. LW – so you have just been dating online? Did you just see what happened to that quarterback at Notre Dame? Have you seen the show Catfish. Your first time should not be with some guy on the internet. Date local. You should be very worried about his history and STDs.

    1. mochamadness says:

      Though I have some misgivings about this particular LW’s situation, I don’t think it’s fair to automatically assume every internet spawned LDR is going to become a “catfish” situation.

      The internet changed the way people interact, and you shouldn’t devalue a relationship with someone just because the internet was involved. However- I do agree that you should take a trip out and meet first before getting serious. You can only get a feel for true chemistry in person.

      1. Look, I think if you meet on eharmony, send 3 emails then meet is fine. That is the way of the world. But 6 -9 months of not meeting. This guy is one of two things 1.) a total liar. He is lying about his past and everything because that big of a player would not be spending tons of time talking to a girl a million miles away or 2.) he is a predator just waiting to hurt this girl.

      2. Avatar photo MackenzieLee says:

        or he could just be a regular guy dating on the internet, or they could have met through means other than the internet

      3. She said they have never met. So the only way this works is they met online. This whole story does not pass the logic test. A regular guy does not court virgins on the internet by talking about his sexual conquests and his kinks. This doesn’t wash. This is gift of fear stuff. If this guy told her these things in person, she would be so creeped out. It feels safe to say these things because it is online. I mean, do you really believe that this sexual animal is really misunderstood and has turned around his life and hasn’t slept with anyone in 6 months because he found his “girlfriend” online?

      4. Avatar photo MackenzieLee says:

        nothing like some good old slut shaming. Having sex with 16 people over the course of what could be 6 years of sexual activity if he started at 16 (which is under 3 sexual partners per year…not really that many for a single young adult) does not make someone a “sexual animal”

      5. By saying this, you are avoiding very real danger here. How many conversations do they have to have telling her that she is a prude and he gets turned on by videotaping before she sends naked pictures? What if this girl flies across the country to find a predator or killer? She will be on Dateline in a tragic video because we can just blow off all the concerns as “Slut Shaming”? Look, when I was dating I dated alot. I was lucky that way. There is no way I would be having an online relationship with someone I never met if I could get a real date with a real guy without a problem. Why would this guy do this if he can easily get a date?

      6. I have to say I agree with csp that this guy sends up red flags. From my own experience, I find that guys who initiate contact with younger women online and want to have in-depth discussions and details about their sex lives and the women’s experience are bad news and often have ulterior motives. When I was 18/19ish, in the early days of Facebook and MySpace etc., I was creeped on by three or four different men, and that was their M.O. – get me to talk about sex and test my limits. I was very trusting at that age and got burned for it. The “I’ve never had feelings for anyone like you” sniffs of manipulation, too.

        Now, IT IS POSSIBLE this guy is just a normal Joe, that the details about sex were offered as part of normal couple conversation, and that there’s nothing weird going on here. But LW, please look back at your relationship and chat/email exchanges and look for these red flags: Did he ask you a lot of personal questions early on, especially about your sex life/experience? Has he ever tried to lead the conversation towards sex or try to get you to open up about it? Did his interest/enthusiasm change when you told him you were a virgin? Do you know for sure you’re the only girl he’s talking to online? Does he send you photos of his body, and possibly ask you to do the same for him? These are the things that can seem like “nothing” in the moment but can be warning signs of a creeper.

        How many sex partners he’s had and what kinks he likes are not as concerning as what his intentions are with you. And as a reminder, should you need it: You’re not obligated to become his #17 if/when you meet. (There’s another red flag – if he’s setting up the expectation that when you finally meet in person, sex is on the agenda.)

        Again, I could be completely off base. But the more I thought about, the more I flashed back to my own creeper scenarios and the more this all sounded very familiar. Proceed with caution, my friend.

      7. Avatar photo MackenzieLee says:

        I couldn’t agree more with this. I was merely stating that by villianizing him for his (semi-promiscuous) sex life alone instead of bringing it up as a possible red flag we lose credibility as a community. Not every guy that has slept with 16 women and meets other women on the internet is a good guy. But not every one is a total creep either. After 9 months of talking, having some conversations about sex is not weird or indicative of creep behavior (necessarily). I agree with your emphasis of when the sex talk started and if sex is something he expects or something they both want. There is a lot of information missing from this letter so it’s best to weigh out all the options instead of jumping right to you’re dating a total creeper….especially if we want the LW to do the unthinkable and actually listen to our advice.

    2. Avatar photo bittergaymark says:

      Please, that guy from ND was so in on it. It’s hilarious how many people buy his BS….

      1. You are probably right, or he might really be that dumb which many football players are.

    3. I met my bf playing a multiplayer online game when we were both 17. We met in person after a year of “being together”. He is not a liar. He is not a predator. He never pretended to be someone he is not. I am none if this things either. He is my first bf. I’m his 6th girlfriend. Unlike the LW’s situation we were both virgins, but just because this guy has some previous sexual experience doesn’t mean he is trying to “catfish” the LW.

      Yes, she should be careful. But ppl like you are the reason why I always avoid telling ppl how me and my bf met.

  2. LW, sex between two loving partners can be incredibly special, regardless of their sexual pasts. That sense of itimacy can be so powerful. However, I wonder why you are planning on sharing your first sexual experience with a man you have never met in person (how I am interpreting your letter).

    1. Regina Chapman says:

      Yes, I wondered about that too. Plus: why have sex right on the first actual meeting? Go, I dunno, feed some ducks or go to an art show or something.


      He sounds like you’ll regret it.

  3. After 9 months you should at least have a plan for meeting. How did you meet? And what does it mean that he has more of an issue with the ldr than you? In addition to plans of meeting do you have plans for this no longer being an ldr? I always worry when people say they have a boyfriend when they haven’t met. I don’t want to sound like your Mom but I would try and make sure the first time you meet is safe for you.

    Everybody has a past. That past with other people doesn’t make a future with you any less special. It doesn’t mean that sex with you won’t be fun or enjoyable because he’s had sex with other people. And it doesn’t mean you have to do things you’re not comfortable with to make them happy. You should be comfortable and feel safe (even if you’re doing this exploring with someone who isn’t a long term partner, you need to make sure you’re comfortable with the situation) before you start exploring those kinks.

    Before you start worrying about his kinks though I would worry about meeting him and seeing if the relationship is something you actually want. It also sounds kind of like you’re planning on having sex as soon as you meet (or maybe I’m just assuming that from your letter). I would recommend at least getting to know him in person a little better before you jump in to this.

  4. GatorGirl says:

    How can you be “committed” for 9 months but only dating for 6? I don’t get it…

    But to your actual question- if you are not comfortable, you are not comfortable! Do not have sex with this guy until you are 110% comfortable with his sexual past and with having relations with him. Is 16 a “normal” number for a 21 year old male? IDK. It depends on who you are. Personally, I’m not comfortable with that many sexual partners. DO NOT let him talk you into sex acts that you are not comfortable with (a video lasts forever BTW). Any person who truly loves you will respect your fears and apprehensions and not push you into something you’re uncomfortable with.

    Honestly, I wouldn’t have sex with this guy. He sounds like someone who preys on inexperienced younger girls. End this relationship and look for one where your comfort level, sexual experiences, and location are more in line. I do not think you should “get over” your discomfort.

    And, please if you go meet this guy, do it in a public place and have a friend on call in case something goes wrong. Do not just meet him at a hotel and expect everything to be fine.

    1. Avatar photo GatorGirl says:

      Oh yeah, I want to add IF you chose to sleep with this man (IF, please please do not do it!!) make sure you see a doctors report for STDs including AIDS, genital warts, herpies etc etc etc BEFORE you have sex. Seriously, you can never be too careful and you do not want to end up with a life long reprocuission from one sleezeball.

  5. Red flag. Bad sign. You are too young to feel like you must make it work with someone who makes you uneasy like this, especially on a topic like sex. Seriously think about wherher this is what you want for yourself. You WILL meet other guys who don’t make you feel this way.

    And my advice for you if you go the other route, use protection and get yourself frequently tested for the love of god.

  6. EricaSwagger says:

    “…when we finally do meet.”

    If you’ve never met in person, this is not your freaking boyfriend.

    1. Thank you. I was going to say the same thing!

    2. can this be the first rule of the DW supreme rules of the dating world? please? the world needs that list.

    3. Oh man, I didn’t even see that part…

      LWs, there’s a difference between “This guy I’m interested in & haven’t met yet” and “My long-distance boyfriend.”

    4. pumpkinbread says:

      lol, i guess i woke up feeing poetic. i totally read the “when we finally meet” as referring to sex for the first time, not meeting in real life for the first time. whoops!

  7. so, there are a couple different issues here..

    1. youve never met this guy? you are planning on having sex with him (“me being the 17th when we finally do meet”), and youve never met him? that isnt a good thing. you cant actually know someone without, you know, KNOWING them. and that includes being in the same physical space. this goes double if you want to have a real relationship and have sex with someone! so, first, get the sex idea out of your head! (side note: i wonder who has the idea that the sex is inevitable: him or her?) sex is off the table until this becomes a face to face real life relationship. that will take immense pressure off of you anyway.

    2. you seem to have some sort of hang-up about sexuality. all your lines about sex being so “special” tell me that. people who think that sex is so supremely “special” usually have been fed that by others, so i would ask where did you learn that sex is so special? tv shows? movies? your parents? well, LW, sex honestly isnt that special. its awesome, its very intimate, and it is special in its own way, but it most definitely is NOT a tv show drama where you lose your virginity to the perfect man (no past to speak of), and then the two of you ride off into the sunset of your forever together. thats just not how it works. sex is just a thing- its just sex. dont put so much pressure on it… if you want to do it, do it. if you dont, dont. dont build it up to be some special all encompassing rite of passage or something, because you will be disappointed.

    personally, i think you have some growing up to do before you get into such adult situations, like sexual relationships and long distance relationships…

    1. lets_be_honest says:

      Don’t really love the idea of saying sex isn’t special. Sex is special to me, and I presume to most people who have it. Just because there aren’t fireworks literally, doesn’t mean its not special. Its certainly more than just a “thing” to me.

      1. well, its special to a lot of people- but i mean its not special in the fairy tale, teenage teen drama kind of way. thats not a healthy thing to perpetuate…

      2. Avatar photo GatorGirl says:

        I’m with LBH on this subject. Sex is special, and for me it is special in a fairytale kind of way. Sure there have been a lot of times when sex was just an act or “thing” that happened in my day, but there are so so many times it is such a special, wonderful, intimate experience. So categorically saying sex isn’t special- I don’t think that’s okay.

      3. you guys are misunderstanding.

        of course sex is special to people. i even said that in my original comment – “its awesome, its very intimate, and it is special in its own way”. what i am talking about is the perpetuated belief, targeted usually at women and specifically at virgin women, that sex is this amazing transcendent experience that will automatically bond you to the partner, leading to “true love” and marriage. that needs to go away. i have lived through that, actually, and if someone had told me as a teenager that sex isnt the be-all end-all special icing on the cake to life and relationships, i would have faired a whole lot better.

      4. lets_be_honest says:

        Its funny, bc I think in a way its smart to teach a young woman that sex is important and special bc they might be less likely to just give it up to whoever and then regret that, but unfortunately, I think many young woman equate sex being special with my bf will finally be in love with me if I do this special thing.

      5. i think that backfires because in our society all girls are taught about is sex, why sex is bad, and how to restrict sex. sex is stressed as being SO important and it needs to be SO special when it finally happens… most women, and most people in general, dont get any other factor of a relatinship stressed- trust, respect, communication isnt talked about. sex then becomes that magic key to the perfect relationship… and thats bad. because, going by that logic, if everything is perfect and then you have sex… boom! instant perfect relationship. you will never break up- you will forever be with that one man, that first man.

        that is why i think its better to teach that sex is just a thing, its just another part of adult relationships. sometimes it might be super special, sometimes it might not. but the bigger things to talk about are the respect, trust, understanding, communication, ect… then, i would think, young women would be empowered to be able to think more clearly about sex, because it isnt built up to be some super-special thing that will *forever* connect you to someone else, ect.

      6. lets_be_honest says:

        I’d prefer to teach that “respect, trust, understanding, communication, ect” are the important things and when you have those would be a good time to start considering having sex with your partner.
        But yea, I agree all of those things should be getting taught, not just 1 part of it.

      7. The thing is though, that logic can get circular real quick. The regret many women feel about their sexual decisions often stems from society’s view that sex should’ve been this magical experience—so when maybe she doesn’t feel the same way, guilt & shame starts to build.

        Also, teaching young women that sex is this big, special, important thing often goes hand-in-hand with placing value on her virginity/purity. Which is gross.

      8. lets_be_honest says:

        It obviously should be a package deal. You teach: that it can be special if you want it to be, how to use protection, birth control, choosing a good partner who respects you, etc.
        I wouldn’t recommend teaching only one of those things. I wonder if the lw has been taught any of them. We’re talking about a teenager who is planning on losing her virginity to a complete stranger who wants to videotape it.

      9. well, to be fair, we dont know if the “boyfriend” wants to videotape it- just that he has before.

        like i said, i wonder who has the idea that the sex is inevitable: her or him? my guess is him. and he is making her think its her.

      10. lets_be_honest says:

        “Hun, I’m really into kinky stuff like videotaping”
        Do you really think he was just sharing this info with her with no intention of videotaping her? Come on.
        Regardless of who is giving the idea that sex is inevitable, she has told us she plans to have sex with him when they meet. This is not wise.

      11. Yeah, I feel like (and correct me if I’m wrong) Katie is saying that the ‘specialness’ aspect that squicks her out has to do less with “meh, sex is NBD” and more with the concept of purity and sex being a “special gift” that women GIVE to men. This seems to be a concept that is shoved down girls’ throats but not boys’. It’s is a harmful concept because in an effort to de-sexualize young women, you’re still sexualizing them by focusing on their sexuality as THE defining characteristic that determines their “purity” or “worth.”

      12. I’m getting you Katie — I was reading this as “sex is a special flower for me to give to my beloved” kind of thing… not a more modern sex is special and should be shared with two people who care about each blah blah blah.

        Plus her inexperience and language tells me that she likely didn’t also get a quality sex education, and I can see this 21 year old taking serious advantage (I’m not a numbers person per se but that is a little alarming given his age and indicates that many were likely hookups and not relationships – which isn’t bad but I think is a bad match with this LW). Plus the fact that she is already thinking about whether or not video taping would be in her future, that’s not where a virgin with her mindset should be!?!


      13. Maybe we need to separate the “sex” and “virginity” conversations. And also maybe replace the word “special” with “serious.”

        Because I agree that sex, within the context of a relationship is important (although it isn’t to everyone), and we shouldn’t teach kids that sex is just whatevs. But I also hate the pristine sparkly pedestal that female virginity still has even in Western culture. Get your eye off my hymen. One’s status should not be earth-shattering.

      14. lets_be_honest says:

        I think you’re onto something!

      15. Get your eye off my hymen TSHIRTS FOR EVERYONE!
        I’d wear one… depending on the graphic 🙂

      16. Love it!

      17. lets_be_honest says:

        I guess the thing to stress to this lw is that sex is supposed to be and can be special, if you and your partner make it that way.
        What likely won’t be special is giving it up to a man you think you are dating for 9 months, who you’ve never met, who has had a lot of partners already and has already announced he’d like to videotape it, with you, someone he has never met, upon your first meeting.

      18. i would hesitate to say that sex is “supposed to be” special. that puts a whole lot of guilt onto people who dont have “special” sex.

      19. lets_be_honest says:

        ok, sex CAN be special, if you and your partner want it to be special.

    2. I’m with Katie on this one… It’s just a physical thing you do. By nature it’s not special. Any “special-ness” is really made up, if you think about it.

      1. lets_be_honest says:

        Maybe I’m crazy, but I would not suggest to a teenager (and let’s face it, 19 is still a teen) that sex isn’t special, its just a thing, NBD. I think there would be a lot less trouble if more people, especially teens, thought sex was more than just no big deal.

      2. actually, if more people thought sex wasnt a big deal, we wouldnt have such slut shaming and guilt in our society…

      3. lets_be_honest says:

        And I could argue there would be a lot less teen pregnancies if more people thought it was a big deal. (and obviously a lot more goes into preventing teen pregnancies, but I do believe this is one of them).

        Let’s not pretend the only bad things that come from sex are slut shaming.

      4. well, really though? how many young women do you think had sex specifically *because* it was a big, important special thing they wanted to have RIGHT THEN that night? because they wanted that special connection forever to that teenaged guy? because that prom night was already so special, sex would just be icing on the cake? because they knew that their boyfriend would never lie or cheat on them because they are in love, and sex makes love real?

        for the teen pregnancy issue, that could be reduced if people started thinking that family planning and birth control was a big deal- something that continually is being fought against, oddly enough.

      5. lets_be_honest says:

        Just kinda addressed this above. See my comment about teaching the whole package. I think its all a big deal, teaching about BC, having sex, who to have sex with, what level of respect you want.

      6. I think you guys are mostly just clashing over what “special” means— sex isn’t something to be taken lightly, for sure, & I don’t think we should use phrasing like “Sex is just body parts touching, no bigs!” (when teaching adolescents about sex)

        BUT I do think the language could be more inclusive overall— placing equal value on the act for both boys AND girls, ~while~ also letting them know it’s okay to examine their own feelings & learning what sex might mean to them, personally. Often, it’s only girls who are taught to wait for That Special Someone, or it’s only girls who are taught that sex is a big deal.

      7. “Often, it’s only girls who are taught to wait for That Special Someone, or it’s only girls who are taught that sex is a big deal.”

        YES! This exactly, and then they go and hookup with a boy who was never taught any of those things, what can possibly go wrong!?! Boys who sometimes can think nothing of passing along his “used” to his friends… and sometimes girls go along because he LOVES me and I MUST SHOW HIM that I really love him or Buffy will end up with him. OMG!…

        I may also be traumatized reading about the Stuebenville OH case, and those boys have not only never learned that sex was special and that both genders should be respected… it seems quite the opposite. Fucking crazy out there.

      8. Avatar photo GatorGirl says:

        This isn’t 100% a reply but here goes-

        I was never given the “sex is special, save it for you husband” talk. Sex was always just a “thing”- I was given the basics, here’s how sex happens and here’s how to not get pregnant/STDs. That’s what it is. So I spent years of my life thinking just that- sex is just a thing and it doesn’t really matter who I do it with so long as I don’t get pregnant or an STD. Now, years and a number of partners later- I wish I had been taught it was special and something that should only be shared with someone who I love deeply and trust and who respect me, etc etc. I wish I had had been taught to wait and waited until marriage to have sex. I wish I had been taught to only share my body with the specialist of people and that sex itself was special.

        So, LW if you want sex to be special, wait until you’re dating someone who is special (or married if you choose) to have sex. Don’t have it with some guy you met online who makes you uncomfortable. Even if you want sex to just be a “thing” in your life, it should always be a “thing” you feel comfortable with and are confident in your decision to do said “thing”. I do not beleive you are comfortable or confident in your decision to have sex with this man.

      9. lets_be_honest says:

        “Sex is just a thing and it doesn’t really matter who I do it with so long as I don’t get pregnant or an STD.”

        THIS. This is exactly what I would hope this teen lw doesn’t take away from this.

      10. well, i think that is just the other side of the extreme, though. what we need is somewhere in the middle, as always..

      11. lets_be_honest says:

        You say its the other side of the extreme, but that is exactly what you are saying. You keep saying its just a thing, not that special. So are you on that extreme side?

      12. um, no. you can think that sex is serious and you can treat yourself with respect in regards to sex without thinking that sex is magical.

        this is amusing to me, because i cant have casual sex (i tried in college and ending up crying in the bathroom because it felt so wrong) and i have only had sex with 3 people. but, i also have actively rejected all the bullshit i was taught about virginity and purity and how sex is so special for a woman and its a gift to give to the right man, bla bla bla. you certainly can have it both ways.

      13. painted_lady says:

        I agree that girls and young women should be taught that sex can be a big deal, and that treating it with some weight doesn’t mean they’re uptight or prudes. I think, though, there are girls who are naturally sexual from the get-go, and so assuming that every woman should treat sex as a very special thing that they reserve for the important people marginalizes them to a certain degree. I think some of the women I know who feel guilt or shame for their early promiscuity only feel that way because of that mentality. Thus the “I wish I’d waited!” from some people (not everyone who says this, obvs).

        At the same time, I think the “Sex should only be for someone you really, really love,” can be used against young women. It certainly was for me – what, don’t you love me enough? Aren’t I really, really special? What, I’m not good enough to have sex with? And yes, of course, being strong enough to stand up to that is awesome – I was, fortunately, because that guy was lame – but teaching people who they should and shouldn’t have sex with can be such a manipulative thing.

        As well, I think the “Sex is special!” mentality leads to a lot of unhappy marriages – so many women around here married the first man they had sex with, and when those marriages inevitably end, then they marry the next man they have sex with. I’m not saying that some of these marriages aren’t happy, but I have one friend from high school who married the guy she lost her virginity to at 16, divorced him after 2-3 years and when she started sleeping with the next guy, she started immediately talking about marriage, not because either of these guys was so great, even according to her, but because she “had to.”

        I think the message we should give girls about sex is, “This is your body, and you get to do whatever the hell you want with it, whether that’s sleep with 70 guys or wait for the ones you’re serious with. And anyone who tells you differently, you are totally justified in denying them access to your body, ever.” Sex in and of itself is not necessarily special, but the decision to have it or not most definitely is.

      14. It’s not “no big deal”, and I would never teach my children that. However, sex is just another part of an adult relationship. I don’t view it as making love or being a physical representation of love at all.
        If it’s special to you in that way, great. I think that for some people it can be that, but sex in itself is not special. It’s PEOPLE and their ideas that make it special.

      15. lets_be_honest says:

        Right. Like I’ve said on here, there is a package of info that should be taught to a TEENAGER about sex. I’m not talking about an educated, adult woman who chooses to have sex with a different man every night. I’m talking about a teen who clearly hasn’t been taught the elements of a real relationship. It seems dangerous to tell this girl that sex isn’t a big deal, which is what katie said and I began to object.

      16. i didnt say sex isnt a big deal- i said that its not going to be the big special event that this LW seems to have built up in her mind.

      17. lets_be_honest says:

        It could be though, if she wants it to be. I doubt it will be if she does it with this guy the first time they meet.

        And you did say that, you said its just sex, its not that special.

      18. no- i didnt. i said that having sex with this guy is not going to be a romantic comedy where the chaste heroine walks away in love and 100% fulfilled. she is hesitating because apparently nothing is “special” to this man anymore, which first of all is wrong and insulting, and second of all implies that virgin sex (or an arbitrary number of past partners (but definitely not 16 partners)) is the only type of “special” sex. honestly, if you want to think that sex is very special, and should be for everyone, you need to let this LW know that just because someone has had sex (even kinky sex!!) before doesnt make any subsequent sexual experiences less “special”. but, above all, she needs to understand that sex isnt a magical thing. she obviously feels like she “needs” to have sex with this guy, and im hoping the reason is NOT because she thinks it will bring them closer. it doesnt do that. sex is not a magical thing.

        there is a difference.

      19. Avatar photo GatorGirl says:

        I completely agree that her reasons for wanting to sleep with this guy are coming from the wrong place and that sex with him will not be a magical/special/made for tv movie moment. I don’t think it is insulting to say this guy doesn’t think sex is special. A lot of people don’t think sex is special, and that its just a pleasurable task just the same as eating an ice cream cone. She has every right to want sex in her life to be special every single time, just like you (and any other person) has every right to think of it differently. It’s not fair for you to tell her she has to subscribe to your definition. Sex can be magically, it can bring you closer together with a partner, it can be special. She could have the magical first time, if she chooses to.

      20. but its not the sex that does that. sex is not a magical thing- it just isnt. if sex leads to you and your partner becoming closer, ect- great. it definitely is a large part of adult relationships. but to say simply that sex itself is (and should be) special and magical is wrong. thats not the way it works. the emotions humans attach to sex are what can make it special. for all we know, this guy might be the real deal and want to make very *special magical* love to her- but neither one of their pasts factors into that. their emotions and subsequent actions factor into that. and, her sad view about sexuality is hurting that.

        i agree that he probably doesnt care about her- they havent even met, what actual commitments can he make to her- but that doesnt mean that she should still subscribe to the belief that sex needs to be some magical thing. all that does to women is guilt them (whether i am guilted because i had non-magical sex when i should have been or you are guilted for not having magical sex after you found out what it was!!) and perpetuates all the shitty views on sex, virginity and women.

      21. Avatar photo GatorGirl says:

        But I’m not saying sex “should” be special for everyone. I’m saying it can be if that’s what you chose! And it sounds like the LW wants to beleive sex is special and she should! It is perfectly normal and healthy way to view sex. Just like your view that sex is just sex is a perfectly normal and healthy view to hold. But neither of you have to subscribe to the others view point. Which you seem to refuse to accept.

        And I do beleive your past factors into it. I’m allowed to feel that way and so is the LW or anyone else. And you’re allowed to think it doesn’t. We’re all allowed to think differently. What is “sad” about wanting sex to be special?? What shitty view am I perpetuating by saying if she wants sex to be special, she has a right to beleive that? Just the same as someone else has the right to think sex isn’t special? How is this a shitty view on virginity and women to say each person should CHOSE how they want to view sex? I’m saying do what you want and let other people do what they want and the BOTH sides are normal and healthy and good. That is like the most accepting and positive stance a person can have.

      22. well, because i really dont think you can “choose” if your sex is “special” or not. what does that even look like? does that mean you only will have sex with someone who has had less then 2 partners? ok. then you do that. and then that guy is a dick and leaves you. nothing “special” about that. then, what if you decide virgins only. ok. then, that virgin is terrible in bed and subsequently cheats on you multiple times because he needs to “sow his oats” or something. there is nothing special about that. so then you wait for marriage. after you wedding and sex your new husband clears out your bank accounts and leaves you for his secretary. how is any of that “special”? how does one ensure that sex is special? im not saying its wrong to think sex is special- i think it is, and i have definitely had special sex- but it just *was*. there was nothing i did to make it special.

        is there really a secret formula to ensure special sex? because if your holding out on us, GG….

      23. lets_be_honest says:

        Sex can be special regardless of what happens after sex. Is that what you’re asking?

      24. so how do you ensure that its special?

      25. lets_be_honest says:

        Depends on the person obviously, but to me I would do so by doing it with someone I have a healthy relationship with, who respects me, who understands what I am and am not comfortable with, someone I love, etc. The basics. If I had those things, I would consider sex special.

      26. see, to me, thats bare minimum. thats the basic requirements for me to even consider sex with a person. for it to then be special… well, thats just something that happens. thats something that evolves as the relationship evolves and emotions evolved and the whole thing gets tied together…

        the things you speak of i hope are just bare minimum for people..

      27. lets_be_honest says:

        Right, they are bare minimums. But the lw is missing all of them. So its prob a good idea to tell her a minimum definition of sex that can be special.

      28. Avatar photo GatorGirl says:

        There is no elusive formula for “special sex”. Everyone’s definition is different. I know that there were quite a few guys I slept with in college for all the wrong reasons (attention, thinking it was the cool thing to do, not voicing a no, etc) and it was never “special sex”. It was just sex. I was unhappy with the decision to have done it and disappointed with myself. Not special sex. On the other hand, with in the parameters of a mutually respectful, trusting and loving relationship I have tons of “special sex”. Even kinky, dirty, special sex. Becuase the person I’m chosing to have the sex with is special and the relationship we’re having sex within is special. And yes, that’s all about the human emotions I’m putting on it, but a lot of people can not seperate them.

        And for your examples, the sex would have been special. Later when the guy did the asshole things, he would just be the asshole you used to have special sex with.

        I guess I’m just not getting why you’re so against the idea of “special sex” when clearly you value sex highly as you’ve expressed not being able to sleep around etc. Clearly to you sex is something you value and only want to share with certain people. And I think the LW should think long and hard on weither this internet dude is someone she wants to share sex with.

      29. i guess, like i said below, if you have never been taught about your “special sex” you dont understand the huge repercussions it can have..

      30. lets_be_honest says:

        Well, your quote was “Well, LW, sex honestly isnt that special.”

        I think we’re talking in circles though and basically agreeing with the important stuff. I don’t think sex = magic = instant perfect relationship. I’m not saying any of that either.

        I just think, and frankly am disturbed that people don’t seem to agree, that you should teach a teenager that sex is special, you should have it with someone you trust and who respects you, you should use protection, not have it for the first time with a total stranger, etc. Just saying sex isn’t special is just as dangerous as just saying that it is. You have to say more than that.

      31. way to take a quote out of context, lol.. this must be what its like to be a celebrity…

      32. lets_be_honest says:

        katie, the entirety of your comments have been stressing how sex isn’t a big deal, its just a thing.

        You seem more concerned that an adult might feel slut shamed by me telling a teenager to be careful about who she has sex with and that it can be special if she’s in a real, trusting and respectful relationship.

        I know your argument against slut shaming. I know how you feel about sex and how everyone should be more open to it and parents shouldn’t make their kids feel like sex is bad. I get that. I agree with that. But I don’t think this is the time for such an argument. This is a teenager who is contemplating losing her virginity to a stranger on the internet.

      33. no, actually, im concerned about a teenager who has a very unhealthy point of view about sex, and is probably going to go through a whole world of hurt trying to have the most special, most meaningful sex she can with a guy who she hasnt even met, probably doing something she isnt even comfortable with (like videotaping) because she thinks that what she is comfortable offering isnt good enough. she doesnt have to think that way.

      34. @lbh — I think some of us who are more concerned about the language of “special” have seen it taught in a religious context related to purity and something that is a gift that results in later submission to your husband, etc. etc.

        I completely agree that people should be taught the importance and specialness of sex — but that it needs to be gender neutral and not related to religion (when taught in conjunction with proper special ed in schools).

        But I am getting the impression that this very sheltered 19 year old thinks that giving it up to her “bf” (who she has never met) will lead to something serious when I think all of us see the red flags of he getting his rocks off and moving on. I mean this guy could have multiple women on the online hook RIGHT NOW… and that’s the “special =/= relationship” piece of this that the LW will be really sad to learn the hard way

      35. *proper sex ed NOT special ed… oy!

      36. lets_be_honest says:

        There is a huge difference between thinking sex = magic and thinking sex can be special.
        Never have I said it will be the MOST MAGICAL thing. I’m saying its important. And if she wants it to be special, make it special by doing it with someone you know, respect, and who respects you, etc. I’m not saying it’ll just be special and then you will get every wish you made because you had sex.
        When I hear you say its not a big deal, it sounds to me like saying to the lw, just do whatever, its not a big deal. I know you’re not really saying that, but I’m afraid that’s how it’d be interpreted by a teenager.

      37. well, in my comment i actually told the LW to take sex completely off the table… im just not sure why you think i mean that its a free for all and she should go for it.

        separating the baggage related to women and sex is hard, i guess, and maybe you dont see the connections if you werent ever taught it in such a package… but the way the LW talks about sex, she is in for a long and hard road if she never realizes that sex isnt the perfect magical special gift it seems that she thinks it is. the fact that she thinks that nothing is “special” for her potential partner anymore is troubling. it means that after she has sex with him, that *she* has nothing “special” to offer anymore… the whole narrative is intricately connected to all the terrible views of sex and women. i just hope this LW is able to get over all that before she does anything sexually related.

      38. Avatar photo GatorGirl says:

        I guess katie I just don’t see how a few comments about wanting sex to be special equal her being brain washed to have this distorted view about “her special sex” that you’re refering to. I just take more simply like “oh well you’ve already had sex, it will just be like a repeat with me!” and “you’ve already done X crazy sex act, it won’t be special or exciting to do it with me!” not thoughts that are part of the bigger over arching religious based arguement I think you’re talking about. I thought for a long time, when my fiance and I would do things, that it wasn’t as “special” because one of us had done it in a previous relationship. Like if it was my first vacation with partner but he had already been on one with his ex, then some of the shimmer is gone. You know what I mean? I don’t think this LW is saying I grew up ultra conservative and think my vagina is a magical make a man fall in love with me forever box. Just that it’s a bummer to think the other person has already done X before so it’s probably not as exciting as it is for her.

      39. That’s not at all what I read Katie to mean.

      40. I read that as “butt sex in itself is not special”. Sorry, I’ll show myself out.

    3. I realize it’s not a fairytale, but I do wish that I’d been a little more picky about losing my virginity. You don’t have to have the perfect man, but I think if you do consider it at least a little special, you are more likely to wait for someone not awful.

  8. Ideally, the past of the person you’re dating should be a non-issue. It shouldn’t matter if they’re a virgin, or if they had 5 partners, or 45 partners. But—& not to talk down to you—I feel like it often matters LESS the older the two people are? At 19 & 21, I do believe your jealous feelings are totally normal.

    So rather than trying to push the feelings aside, I think you should try to understand why they’re there. It’s totally possible for someone with more sexual experience to be with someone who has none— if this guy is sensitive to the fact that you, well, are a virgin, then hopefully he’ll use his experience to show you a good time & gradually introduce you into kinkier stuff (as long as you’re comfortable).

    BUT— “I don’t want to do things he’s already done because I feel as if it won’t be special to him”— it doesn’t sound like you’d be cool with that scenario. And that’s okay, too. If you want your first sexual experiences to be with someone who’s on a similar page to you, so it’ll be “special” & you can explore together, then maybe this guy isn’t right for you.

    1. A guy told me his number is somewhere around 1600. Not to be a total bitch, but my thoughts were:
      1. Ewwww
      2. That’s probably a lie, but if you’re the type of person that thinks that’s impressive, you aren’t very mature.

      1. 1600? That sounds like a lot of work…

  9. What everyone else said + DO NOT LET THIS PERSON VIDEOTAPE YOU.

  10. LuckySeven says:

    1. Until you guys have met in person, how can you really know him? For right now, it might be better (and less stressful for you) to take sex off the table. Make sure you meet him in a public place, like a coffee shop or restaurant, and let a good friend know where you are and when you’ll be back. I get it; it’s long-distance, but it’s a red-flag that you guys have not met up in person or at least Skyped (though that’s definitely not the same thing!)

    2. Overall, I wish that people, myself included : ), stopped caring about whether or not our feelings are “normal”! It’s okay to feel however you want to feel. A lot of times that’s our intuition/ common sense radar, and it should not be ignored. Rather than trying to ignore it or determine if it’s normal, what is the feeling trying to tell you? Maybe that sex is important to you, and you want to wait til the right person and time? That’s more than ok! Good luck.

  11. yeah, i’m super confused by the description. If you haven’t met in person, you are NOT dating! And what does committed vs dating mean if you haven’t even met?

    In general, past should not matter, and all experiences will be firsts together and will be special if you really love the person. However, given your complete lack of experience and his overabundance of experience (plus, the long distance, and potentially never met thing??), you are most likely going to get taken advantage of. Find someone more your speed to enter into the dating world. At 19, there are very few of your peers who are actually as experienced as they would like to be, so you are not alone.

  12. He’s 21 and has had 16 sexual partners already, and the long distance is “more of a problem for him”. LW, sorry, but by the time you meet in person, I’d bet a 17th sex partner would have already happened. It just doesn’t seem likely that he is as “committed” as you are to someone he’s never met in person. I think you need to lower your expectations in this “relationship”. Someone you’ve never met in person is not your boyfriend.

    1. I was thinking this same thing.

  13. You can’t officially date someone you have never met. You can have a relationship of sorts with them but nothing that inolves commitment or officially being together. And it’s disturbing that someone who has never met you is planning to videotape you having sex. Don’t you find that odd? In your mind I know you think you are in a commited relationship of 6/9 months but may I suggest you start the clock after you meet? Don’t have sex with him until you have been physically together for some time. Until he takes you out on dates, until he earns your respect and trust so that you feel comfortable with his commitment to you…Until you feel comfortable that you aren’t another notch on his bedpost – or video in his library. Take it slow. As slow as you need it to go. If he pressures you or complains then he isn’t the guy you think he is. And if you think you have to jump though hoops or make your screen debut to keep his interest then you aren’t ready for sex with anyone.

  14. LW you may want to consider having sex for the first time with someone who has a lot of experience (not saying this particular guy)…its not going to be special anyways because losing your virginity is painful and awkward (due to inexperience)…having sex with someone inexperienced (another virgin for example) would make the situation that much more challenging…just use protection (regardless of how many partners the guy has been with – it only takes one time to catch an std)…that’s my weird take on this situation

    1. LW, this is not true. Sometimes first-time sex hurts, sometimes it does not. My first time was a wonderful experience, and I am so glad I shared it with someone I loved and trusted. Don’t miss out on a beautiful experience because you want to rush into bed with this creep.

  15. I think that you are thinking the way you are, because at some level you recognize as many red flags as we do. Please do not remain in a ‘committed relationship’ with somebody you know only over the internet. The internet allows people to pretend to be whatever they want to be at the moment. It is easy to be ‘committed’ to dozens of LDRs simultaneously. Prison inmates do this for jollies, because they have litle else to do. So do married men, guys off working on oil rigs, etc., etc. You are young and inexperienced enough that what you need is varied, in-person dating experience, not leashing your heart to a guy you haven’t even met. If you do meet this guy in person, you don’t want your first date to feature sex. I have no idea what sort of ‘dates’ you’ve been having for 6 months, if you have yet to meet this guy in person or what exclusivity meant prior to your first very-hard-to-understand-internet date. After several in-person dates at the minimum, if you do choose to have sex with this guy, please, please, please do not let him videotape you and don’t have sex in a place where he may have hidden a videocam — unless you really want to have a nude sex tape flitting around the internet. Actually, this guy sounds pretty creepy with the videos.

  16. spark_plug says:

    LW – have you seen and talked to this guy? Like in a video chat, not just pictures or over the phone? Your description is super confusing, and I hope that you’re not “dating” a guy who’s lying about his age, is married or in a LTR and goes online to meet people on the site. How many DW have we read of women finding out that their men have been trolling for company online..

    My personal rule of relationships: If I didn’t get to know them by seeing them 2-3x a week for a number of months, it’s not a real relationship. Period. I don’t care how wonderful the conversation is..

  17. “Date” = a meeting of two persons where at least one have a “romantic interest” in the other. Will this next generation of people even realize that this is the actual definition of a date? When you say you are dating someone, that means you’re going on dates, or at least have hung out around each other enough to develop a romantic connection. YOU CAN’T BE “DATING” IF YOU’VE NEVER MET IN PERSON! I feel like such an old granny fart when it comes to this stuff. But I swear, if my future children start “dating” exclusively through their computers I’ll go crazy.

    As for this particular LW, other than the glaring issue of having never met this person, there are various others. He has a problem with the ldr? Well why is he in one then? Why in 9 months have you guys never made an actual meeting happen? Why, if you feel apprehensive about having sex with someone with so much experience, can’t you just talk to him about it? This whole situation, along with your very young age, indicates to me that you really shouldn’t have sex with this guy any time soon. You should probably back away a bit, make plans to meet (in a safe public place), and put your romantic feelings on hold until then. Honestly, you cannot develop a romantic connection solely through your computer.

    Gah, but I sort of feel like someone this young who would develop this kind of “relationship” with someone online isn’t going to suddenly start listening to advice like mine. I feel like our views of the world might just be too vastly different. So whatever. Maybe she’ll just have to get her heart broken from the whole thing, live and learn. Or maybe he’ll be an elderly woman and she’ll live and learn from that. Or maybe he’ll be prince charming and will be awesome in bed and they’ll fall madly in love forever. Bleh.

  18. A lot of people are trying to give you advice on whether or not you’re really “dating” this person, or whether he is your “boyfriend” or not, and how wrong it is to have sex with a stranger you’ve never met, or how to make different decisions, but this is all very subjective information. Here is everything you need to know about your situation:

    If you’re not comfortable with it, don’t do it. It’s pretty simple. Some people would be perfectly comfortable going through with a situation like yours. That doesn’t make them any more “right” than you are, it just means they would be comfortable doing it. Everything you think, or believe, or do IS normal. It’s normal to you, and that’s all that matters. Forget about how unorthodox your relationship may be, or whether what you are feeling is real or not, and just focus on what you want. It is the simplest question you can answer that will give you all the advice and guidance you need.

    1. lets_be_honest says:

      I agree with most of what you’re saying, and I really like the ‘do what you are comfortable with’ but this…”Forget about how unorthodox your relationship may be, or whether what you are feeling is real or not, and just focus on what you want.”
      Maybe its just me, but am I the only one concerned about telling a teenager to just focus on what they want? I wanted to do a lot of things when I was a teenager that were extremely dangerous and unwise.

      1. Avatar photo GatorGirl says:

        I totally agree with you that we should not be teaching our youth to just do what they want.

      2. I agree – there’s a reason they are not officially “adults” until 18, they do need guidance and direction as they’re brought up. But here’s the thing about bad decisions: it’s life. You, me, everyone makes them. They are going to happen no matter what. Often, people who makes mistakes are better people in the end because of it. This is how you gain “life experience.” No matter how many times you tell a person “if you do X, then Y will/could happen,” they are still going to think they may be the exception.

        The LW sounds like she is approaching this correctly. She is hesitant and uncomfortable with the situation and feels like she should rethink this. She also feels that maybe something is “wrong” with her for thinking so, or what she can do to change that feeling. And my advice to her was exactly that – don’t. There does come a point where we need to give people a certain amount of credit. She recognizes this is maybe not for her, or the guy she knows may be a little advanced for her. She needs to listen to that. What she doesn’t need to listen to is how fucked up her decision making paradigm is. If she wants to “date” a guy she met on the internet, let her. She is being smart about it, otherwise she wouldn’t have wrote in wondering if her thoughts are “normal” or not.

        I’m not saying let kids run free and do whatever they want. I’m saying that they should pay close attention to what THEY want – not what they THINK they want, or what society thinks they should do, or what their friends do, or what other people do. She’s going to make stupid decisions in her life, and that’s fine. But it does appear she is approaching this situation in the right way – cautiously.

      3. She’s 19 FFS — not 14. She’s old enough to be in the military and be killed for her country. Can we stop with the overprotecting of an adult woman!?! Yes, she’s inexperienced, but she’s not in middle school.

      4. lets_be_honest says:

        She’s an inexperienced teenager by definition.

      5. lets_be_honest says:

        One who clearly hasn’t been taught much if she’s saying she’s in a relationship for 9 months with someone she’s never even met.

      6. Thinking she’s in a relationship has nothing to do with her age… plenty of folks of all ages get sucked into thinking the internet is more real than it is.

        I guess I look at is as she can start to grow up and becoming the functioning adult she already legally is, or she can continue to be sheltered and coddled. She’s too to be sheltered, she’s legally responsible for her decisions. If she gets videotaped — it’s not child porn that can at least attempt to be removed from the net — she’s an adult who starred in a video with a guy she met online.

      7. *She’s too OLD to be sheltered.

        Damn my typing is terrible today. That’s what I get for half watching the inauguration while DWing 🙂

      8. lets_be_honest says:

        Giving advice that she asked for isn’t coddling though.

      9. Agreed, that’s why I’ve given her the advice that I have, as well as tried to raise some red flags for the LW to think about in the future.

      10. That was exactly my takeaway as well. Wanting to do something ≠ Being comfortable doing that thing. I was pretty mature at 19 (thought I was MORE mature than I actually was lol, but still pretty mature), and I did a heck of a job convincing myself I was comfortable in certain situations (sexual and otherwise) when I wasn’t really comfortable just because I really wanted to do those things for a variety of reasons. For the most part, I was pretty good about trusting my intuition, but the biggest mistakes I made were when I ignored it.

        It seems pretty clear to me that the LW is totally uncomfortable with losing her virginity to this guy. But she wants to do it. LW- you don’t have to have a iron tight reason for not sleeping with this guy. Simply honoring that little twinge in your belly that says ‘this doesn’t feel right’ is plenty reason to turn him down.

        Now my two cents on the situation are this: I personally think that the fact that you’ve never met him in person is the biggest reason for you to not have sex with him, or at the very least to wait until you’ve interacted in person for quite a while before you consider having sex with him.

        I fall in middle of the debate going on in this thread. Sex is different for everyone. I personally find that my mindset is what defines a sexual experience. I was already in love with the first person I had sex with, so having sex with him bonded us more. After him, I got antsy and wanted to explore. So the next few people I slept with were just for fun. I liked those guys just fine, but I had NO INTENTION of having a romantic relationship with any of them. And I found that I’m able to separate sex and emotion pretty easily because when I fell in love again- the sex was intimate again. But you might not be that way. I have friends who fall head over heels in love with every guy they sleep with. Friends who don’t give a shit about sex at all. Friends who waited until marriage. Friends who view sex as just a thing. Friends who wait to have sex until they’re in love. The only way to find out how you view it is to really really try to honor your levels of comfortability. But again, to me, it sounds like this guy isn’t making you feel comfortable.

  19. temperance says:

    I remember having the same worries as you did when I was in high school, LW. I didn’t want to be with a guy who had more experience than me doing stuff that was more serious than making out, because I wanted those firsts to be “special”, too.

    I lost my virginity to my first serious boyfriend, who was also a virgin at the time. We broke up after a little over a year of dating, and I have zero regrets about my choice. I haven’t seen the dude in maybe 5 years or so, and I’m okay with it. I didn’t worry about contracting an STI from him, or that he was going to play me like he played those other girls he had sex with.

    In short, LW, please don’t let your first time, which is obviously important to you, be with this guy. Let it be with someone you meet in person, fall in love with, and who hasn’t had a significant number of partners, because that’s important to you.

  20. So, you’re not in a relationship with this guy if you haven’t met. You shouldn’t plan on having sex with a stranger. You should only meet him in a public place. I do think it’s a red flag that you guys haven’t met yet. Don’t let someone videotape you having sex (specifically a guy you barely know). I would suggest looking for someone who lives near you that you can interact with in person and who is more on your level of sexual experience. I generally don’t think sexual pasts matter a lot (aside from the obvious, STDs, etc.), but I think that you may be getting in over your head and could be putting yourself in a lot of danger by the path you’re taking with a stranger.

  21. You Go Girl says:

    You are not required to “get over” your discomfort that your boyfriend is 21 and already has had 17 partners. Your are uncomfortable because 17 partners is a lot for someone who is only 21, and this is a normal reaction.

  22. Sorry LW, but this whole post is just ewwwww.

  23. First, I need to agree with everyone else. Do not have sex with this guy. You are not dating. He is not your boyfriend. He is, at best, a penpal and at worst, a predator using the internet to seek out naive youg women to videotape having sex for his own use or maybe even for public consumption. Listen to your gut. If you are not comfortable, don’t do it.

    Second, just because someone has more sexual experience than you, does not mean that sex with you would not be special. Being with a new person makes it different and exciting. If that were not so, people would have sex once and never do it again. But they don’t, do they? Someone who really cares about you would be patient and understanding about your inexperience. Having said that, please pick the right guy to lose your virginity to. Someone with whom you feel comfortable, someone with whom you have an emotional connection. Someone who understandings your feelings. (I picked the wrong guy and it put me off sex for a while. Don’t be me.) Sex is like anything else: it takes practice. But be smart about it. Use protection, make sure you and your partner are healthy, and make sure you feel safe with him. This guy isn’t it.

  24. OMG this girl is getting played. Let me spell it out for you.

    He is going to bang the shit out of you, in every way he can, then he is going to move on.

  25. Maybe he’s never had a virgin. There you go…

    In all seriousness, *I* would be bothered by that number (seems out of proportion for his age, but I’ve been out of commission for a while), and I don’t even really care about “numbers.” I also won’t be videotaping it anytime soon, so if you aren’t sexually compatible on paper (or on email, as it were) then you might want to just cut your losses and run. Meet an actual, in-person guy you have more in common with that doesn’t scare the pants ON you.

  26. Also, I know that opinion varies about how much to disclose to previous partners about sexual relationships (personally I am a NO on telling the # and my husband has never asked; big YES or sharing any history of STDs, abuse, etc. that could seriously impact the relations) but is anyone else thinking it’s really fucked up that this guy has apparently shared all these stories about his sexual past, to a virgin, who he has never met. Sounds like he’s grooming her like he has others… I bet he’s irritated that it’s a LDR, that’s what he tells all the ladies 😉

    For that matter – how does someone who you’ve never met know if you are a virgin or not. MEET FIRST PEOPLE!!! DETERMINE THAT THE INDIVIDUAL IS REAL before sharing the personal and intimate details of your life.

    1. YES, and maybe I’m just paranoid and cynical but I’m worried that he preys on virgins and probably doesn’t keep his videos as private as they should be.

      1. painted_lady says:

        I had that thought, too, actually – how many of those 16 women were virgins before he got to them? Maybe this is my own personal experience, and the LW didn’t specifically mention this, but I think she would have, if a man (or woman) isn’t at least more cautious/considerate about rushing into sex with someone who has never had it before, this person is probably not going to be a good first partner.

  27. Avatar photo Northern Mermaid says:

    LW, There are a few red flags about this guy. The fact that you’ve never met, the suggestion that he’s expressed an interest in videotaping you, and your own discomfort about him. I agree with most commenters that you shouldn’t sleep with this guy. However, just because he’s had 17 partners in his 21 years doesn’t necessarily make him a giant STI-riddled horndog out to prey on unsuspecting young women. Let’s say he lost his virginity when he was 15. That’s 6 years of sexual activity and 2.833333 (3ish) sexual partners a year. “Slut-shaming” is not a nice thing to do, regardless of gender.

    Like I said, I wouldn’t sleep with this guy because of the other red flags. As for your “how do I get over this?” question, I’d say that you can’t really. Jealousy is really shitty because it’s SO hard to control, especially jealousy of something that happened in the past. I haaaaaaaaaate that my s/o had a really really serious partner before me, and I bet he’s not stoked that I have had way more sexual partners than he has. For me, I find the best way to get over jealousy of the past is to be conscious of the moments where you are feeling happy and confident and affirmed in your relationship. Cherish those, and don’t let them pass by unnoticed. After a while, your insecurity about your relationship will wane and so will the jealousy.

    That being said, you can’t really be conscious of those moments because you probably haven’t had them since you’ve never met. Meet him, pay attention to the voice in your head that is telling you to be careful, and go from there. You might find out that he’s actually wonderful. You also might find out that he’s a total skeeze. You’re an adult, pay attention and make a decision that’s right for you. If he turns out to be someone you want to be in a real relationship with, (take it from someone with plenty of sexual partners) sex with someone you love and are invested in is totally different and it is “special.” Try not to get your head to wrapped up in making sex new and exciting for him.

    So, short version: Meet the guy, trust your doubting voice, use a condom (always, not because he’s had sex with lots of people. Always always always use a condom), and maybe watch Catfish. There are hour long episodes on MTV.com.

  28. I remember when I was your age, I had been pretty sheltered my whole life and finding out that the guy I liked wasn’t a virgin was pretty upsetting to me, so you’re not alone in that. In my head, I really thought that everyone was like me, and that when I did fall in love it would be with someone exactly like me. That being said, when it did finally happen (2 years later), I was ready – although I wasn’t the first, it wasn’t a big deal anymore because I knew he loved ME. I had done a lot of growing up.

    If you really can’t get over his past, and if it upsets you to the point where you only want to do new things he’s never done before (which sounds like a really scary prospect to me, if this guy is as experienced and sexually adventurous as you say), maybe it’s a deal-breaker and you need to let him go.

    If you do go through with it, do NOT have sex with him without him getting tested for STDs and wear a condom every time. You’re young enough that I hope you’ve had the HPV vaccine too, because that is a pretty scary one that affects almost everyone and is impossible to test for in men. If he’s had unprotected sex at all, he most likely has it with sexual numbers like that.

  29. mochamadness says:

    LW, I know it seems harsh, but everyone here has really sound advice. It is impossible to know if you even WANT to have sex with someone before you meet them. And when you do meet this guy, you should make sure it is casual and friendly, not a situation in which you will be pressured to have sex. I would suggest taking a trip to his city with a friend or family rather than going alone, or insist that he come to your town and stay somewhere other than your house.

    You really have to take your own comfort level into consideration. If your mind is saying “I am uncomfortable with you having 17 partners and me having none” then that is probably how you are always going to feel. I agree with previous posters.. you are not required to be okay with that. Everyone has their own “dealbreaker.”

    Just take it slow and listen to all of the little voices that tell you when something is off. Never have sex with someone just because you feel pressured. Sex can mean different things to different people, and no one (not your partner, not your BFF, not all of us on DW) knows when you’re ready more than you. Be safe!

  30. You Go Girl says:

    I should add that the LW never says that she met her boyfriend online, or that they have not yet met. She says that they are in a long distance relationship, and that she finds it difficult.

    1. Well she does say, ‘I am a virgin and he has had 16 partners (me being the 17th when we finally do meet) and that really bugs me.’ At least to me that sounds like they haven’t actually met. She doesn’t go in to specifics on how they met, etc which is leaving things open for speculation. But, really how would you “date” (chat/talk/whatever) someone for 9 months without meeting them in person without the internet?

  31. Avatar photo fast eddie says:

    I’m taking on the positive side of his being experienced. He’ll most likely be a better lover for having some experience and the first time should be special for both of you. To feel physically and emotionally protected set down some ground rules. The LW considers making a video kinky, therefore make that a HELL NO! plus anything else she’s uncomfortable with. Insist that he get tested before hand just to take STDs off your worry list. Do some research to build some confidence and try some self satisfaction to have a notion about what does and doesn’t feel good. His numbers aren’t all that high so it will indeed be special for him after waiting 6+ months with nothing but masturbation for relief. I’m worried for him that her inexperience might not leave him satisfied. Time will tell if they can survive the first awkward sessions but don’t give up too soon and let your heart and brain guide you. Sex is just like anything else, it gets better with practice.

  32. Avatar photo MackenzieLee says:

    One week into ending the long distance part of my 5 month LDR, I can say a lot changes when you are together. It might even be harder than the distance is. As some people mentioned above, before you decide about this or any other part of the future of this relationship make sure you have an end date planned for the LDR. Wendy had a wonderful post about what is needed for a sucessful LDR.

    On to your real question. Only you can answer if this is a deal breaker for you. It is definitely not impossible for the sex to be incredibly meaningful for BOTH of you. Sex is quite different with people you care about than with random people you may or may not know (which some of those 16 must have been). For now work on making sure you know what you are comfortable with and want to do (and remember EVERYTHING ends up on the internet….so maybe no to those videos).

  33. painted_lady says:

    LW, you seem to me to be looking for a “good enough” reason to be uncomfortable with this whole situation. You know what the best reason of all to be uncomfortable with this is? The fact that you already are uncomfortable.

    Just because you have already agreed to have sex with this guy (or at least, not disagreed) does not mean that you will be backing out of a bargain if you change your mind. You’re not breaking a contract. You’re not a used car that can be taken back to the lot for a faulty turn signal, and if he tries to guilt you for not making good on your end because he bought a plane ticket/took time off work/got his hopes up, then he’s a piece of shit. Don’t date any man who treats you liked used at he bought, and certainly don’t have sex with him.

    Also, this guy? You don’t know him. You don’t know someone till you meet them face-to-face. There are some people on DW that I feel like I know pretty well, but for all I know, Katie could turn out to be a 15-year-old dude. Sure, I’ve seen pictures of her, and we’ve known each other online for a couple of years, but who says she didn’t steal all of those pictures and create a fake FB profile? And even if she’s exactly who she says she is, if I ever get to meet her someday, she could turn out to give off a totally creepy Single White Female vibe. I have no way of knowing that till I meet her for the first time (I’m sure you’re completely lovely, though!). If I ever make a trip up her way, you can be damn sure I’ll be meeting her for drinks or dinner or both…but I’m not going to ask to crash with her. I don’t crash with people I’ve never met, and I don’t ask them to put me up for the night, because that isn’t a safe thing to do. Not only are you planning on crashing with someone you’ve never met, YOU ARE PLANNING TO HAVE SEX WITH HIM. This is not safe, nor is it smart. Meet up with him, sure, but don’t agree to be alone in a private place with him the first time you meet him. Don’t meet him in a way that will leave one of you stranded if you don’t stay in the same place. Take it off the table – take the pressure off for both of you, and agree that sex will not happen until the second meeting.

    I get feeling emotionally ready for sex and having nowhere to put that emotion. I didn’t have PinV sex till I was 23, and by that time I was climbing the walls. In retrospect, I can think of about five guys other than the one I finally had sex with who would have been perfectly fine firsts, but in that moment, I wasn’t comfortable with having sex with them. I sometimes felt like I was going to die a virgin, and everytime I turned a guy down, that feeling increased, and I wondered if I was giving up my last good chance. But you know what? I did finally have sex. I was completely comfortable with the guy, it was lovely and safe….and then in the intervening seven years, I’ve more than made up for those five or so years I was waiting for a moment that felt right to me.

    1. haha… oh, PL, you crack me up.

      seriously, though, LW- listen to your gut.

      1. lets_be_honest says:

        loved that too.
        And then took a minute to figure out what Pinv sex was. p in v, for any other idiots out there.

      2. painted_lady says:


  34. tbrucemom says:

    1. This guy is not your boyfriend if you haven’t even actually met him.
    2. To think that he’s gone without sex for 6 months after already having 16 partners at 21 is stupid.
    3. Sex is special with someone that you actually are in a relationship with whether it’s your first or 17th or 30th or I think you get the point.
    4. I guess I’m just kinky but I get turned on when I hear about my fiance’s past sexual partners. I was married for a long time so I’ve only had a couple of partners and it also makes me feel special to know that I’m the last one he’ll be with.

  35. I think that if his sexual past is worrying you so much, then you are not ready to have sex with this man. Particularly for your first time, I think you should be with someone that you fully trust and respect. When you are in a trusting and caring relationship, the sex will be special. And even if he’s had a lot of experience, there’s still some things that he hasn’t done. I know my husband had more sexual experience than I did, but I’m the only one that he’s had sex with in a hostel! You can find plenty of firsts if you look for them.

    And how do you even know how many women he slept with? I’d suggest that in future relationships, don’t let this topic come up. I myself prefer to not know, because I’d start thinking things like you are thinking right now.

    1. Temperance says:

      See, I need to know before I jump into bed with a guy, and I’m always willing to disclose, too. Granted, I’ve been in a relationship for 8 years, but it’s important to me to be with someone who shares my morals. Someone with a very high number would not be that person for me.

      1. Avatar photo GatorGirl says:

        I perfer to know as well. There were times when I was younger that I didn’t ask before hand, but now if I was to start a new relationship I would ask up front.

  36. sarolabelle says:

    I’m a little late to reply but I hope the LW is still reading. I am 31 years old and two and a half months ago I married my husband. He is also 31. We were both virgins when we got married. Yep, we both had zero partners. It is something you can have too if you want it! With no other sexual partners I didn’t have to worry about STDs or him comparing me to them. It is possible if you are willing to wait for the right guy to find someone who is willing to wait for you (if that is what you want).

    Should you have sex with a guy you never met? NO! I once wasted 4 months of my life talking to a guy on Skype and he was cute, we got along great. And then we met in person and he was 4 inches shorter than me and we didn’t get along at all. And he asked if he could kiss me and we did and it was gross! YUCK. There went the 4 months I spent getting to know him. Oh well. Live and learn.

    Should you be worried about a guy who has 16 partners? YES. I had a rule on all guys I dated. They had to have less than 5 sexual partners. If they said 16 I would have ended it.

  37. Nothing good will ever come of being video taped during explicit acts. You don’t need to do anything you don’t want to or that you aren’t comfortable with just to prove a point. And yes, you should be worried about someone whose had 16 partners because of STDs. When was the last time he was tested? I’m also curious as to how you’ve been dating for 9 or 6 months without ever meeting. Is this an internet relationship? My question would be, is it normal for a 21 year old man to meet a 19 year old virgin on the internet and give her a detailed list of all the sexual acts he’s performed with 16 different partners? That sounds really shady to me.

  38. Anonymous says:

    I’ve actually been in the exact same spot as you, LW. I had an online relationship when I was 18, for about 6 months and it fell apart. The man refused to meet me in person, despite our emails and phone calls. He repeatedly flaked out on dates. If this guy is seriously interested in you he would have reached out to you months ago to schedule coffee, or dinner or something. Most guys try to meet women they’re interested in because it’s efficient for everyone.
    You need to reach out to him and date him in person for at minimum 6 months to verify his interest. If it lasts that long then yes, he’s probably serious. But also know you should take your time sexually. Don’t feel like you need to rush to give your virginity to someone you love, when you could take the time to explore yourself sexually through masturbation, etc. It’s not his number of partners that is sketchy but rather the fact that you guys have never met regularly in person.

  39. I was (basically*) a virgin when I started dating my current partner, and what I can say is that your having sex the first time with your boyfriend won’t be any less special just because he’s had previous partners. If he’s really into you, it’s going to be special for him as well as you. I think it’s normal to be nervous about this sort of thing, but I don’t see any sense in being jealous. Then again, I’m not a particularly jealous person.

    *I don’t really count my ‘first time’, given that he (different guy than I am with now) was too high to keep it up. Long story.

    1. Oh, and as far as kinkiness goes, that’s something you should explore together AFTER you have sex a few times. Most couples who have kinky sex don’t start out with all the whips and leather. They work up to it. That’s how you figure out what you like and what totally turns you off.

  40. Noooo…..No, seriously, a big fat no. The fact that he is so open about his kink of video taping to his virginal gf he has never met is a big fat warning sign. Nothing wrong with being kinky, but it seems like he is laying the ground to try and manipulate LW into agreeing to be videotaped. That said, there is nothing wrong with someone who has that number of partners and it doesn’t mean that the act won’t be special with you. As far as numbers go, different strokes for different folks. Some people are far more comfortable with casual sex than others (I’m not one of them, so I can sympathize with LW), but as long as they are being careful it doesn’t mean that they won’t value sex with someone they are in a long term relationship in.

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