His Take: “I’m a 28-Year-Old Virgin. Does That Scare Guys Off?”

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His Take questions are answered by our panel of smart, opinionated, and funny dudes.

I just read your responses to “Does My Virginity Turn Guys Off?” from a few years ago. It was great advice, tailored for a young woman who was 20.

I am a woman who just turned 28. Though I am not particularly prudish, I have been working under the assumption that even with the best birth control, scientifically speaking, a baby is a possible by-product of sex. My mother raised my sister and me as a single woman with a lot of love but not much financial stability. I understand all too well the struggles that single mothers (and their children) face.

Although I am not religious and am very liberal, I am politically pro-choice but personally pro-life. So, I’ve been holding off on sex until I meet someone who would be a really fantastic father and/or when I can provide some stability to my hypothetical child. I’m now 28, have a graduate degree, run a non-profit, and am in a financially healthy place. I’m attractive, pretty confident, well-traveled and well-read. Lately, I have been going out on an insane number of dates and really enjoying myself.

In the past, I never articulated my reasons for holding off to any guy I’ve dated. However, I fear that what I consider to be a practical decision gets misinterpreted when I say, “I’ve never done this before.” I’ve been given advice from other women that my reasoning is too intense for guys to hear. Do you think that is true? How do you suggest maneuvering this topic now that I feel ready to have sex? A simple google search on this topic does not yield any results that fit my situation. — 28-Year-Old Virgin

Screen Shot 2014-01-08 at 7.14.33 PMBrian:
The next time you’re in a situation where you could lose your virginity, here’s a script you can use:

HIM: Do you want to… you know?
YOU: (laughs nervously): Ah, yeah, sure… I just want you to know something beforehand. I’m a little inexperienced at this.
HIM: (laughs nervously to show he is also nervous and that it’s acceptable for you to be nervous): Okay. What’s “a little inexperienced?”
YOU: I’ve kinda been putting this off because I’ve dated guys and not really liked any of them, or trusted any of them enough [fill in your own explanation here] and I just need to know that you’re up for any consequences that might emerge.
HIM: Ah, I see. Yeah… I’m well-aware of the small percentage of risk involved. You’re on the pill? Then I’m willing to if you are.

Before this conversation, you will probably already know if the specific cherry-popper is a trustworthy dude because, if there’s any question in your mind, your Single Mother Warning System will bleat like a dying sheep again and you’ll stop yourself. Which is a good thing — stopping yourself from sleeping with a jerk. Instead, find a dude who is reliable and a good listener, and you’ll have nothing to lose. Well, except, you know, for that one thing.

P.S. One more pointer: You say “I feel ready,” which is different from a more determined “I am ready.” Keep telling yourself: “I am ready. I am worthy. I am going to be fine.” And you will be.

lo-res-175Jarek:I won’t sugar coat it, unless you are meeting guys on ChristianMingle, you are going to get some disconcerting eyebrow raises when you share the news that you are a proud card-carrying member of the V-Club at the age of 28. But, you are at a good place in life, actively dating, and are now okay with the idea of meeting a decent man and possibly having a baby. When you finally meet that guy and you both know there is a future, trust me he will not see this as an issue and “the talk” will not be as difficult as you are anticipating. If it is “too intense” for him to hear, he’s the wrong guy to be losing it to in the first place.

Now, on the other hand, if you are looking to just get it done and don’t really care if it’s with “the one,” then you don’t even need to bring it up with the guy. Your sexual past is really none of his business in this situation. If you do feel compelled to discuss your experience and feelings on your first time, go to your girlfriends.

Screen Shot 2014-02-22 at 7.39.04 PMDiablo: You seem to want your life absolutely sorted out before you act, never risking an unwanted outcome. But to find love (or sex), you have to make yourself vulnerable and take a chance, because the other person will be taking a chance on you. And people have sex ALL THE TIME without getting pregnant. Fear of pregnancy is really not a convincing reason not to have sex. Seriously, I’ve been sexually active for 30 years and no one ever got pregnant. Birth control works pretty well. Use two kinds if you like. If, OMG, you did get pregnant, well, people like your mom occasionally survive this and raise some awesome kids.

But if you want to nail down your entire future life plan as a pre-condition of getting some, even the most honorable guy might not make that deal. Especially in that moment. Wilt! Get some condoms and go for it already. Say only, “I’m not too experienced.” Hope only that he cares about your pleasure. Then order some Chinese food.

Dennis Hong Headshot - SmallDennis Hong: I can tell that sex is something you’ve put a mountain of thought into. And that’s awesome. I used to teach at a high school for at-risk kids, and I only wish my students put half as much thought into sex (well, the consequences of sex — I’m sure they put plenty of thought into the act itself) as you.

At the same time, I think it’s also possible to swing too far the other way. This statement, in particular, raised a tiny little red flag in my mind:

“I’ve been holding off on sex until I meet someone who would be a really fantastic father, and/or when I can provide some stability to my hypothetical child.”

While this is an admirable goal, the problem is that his being a fantastic father, or you being able to provide for your child, is not something you can ever know with 100% certainty before you even have sex with the guy. He might be a douchebag putting on his best facade to seduce you (because that’s what douchebags do)… you might get crushed by a meteor and orphan your child (because that’s what meteors do)… there’s just no way to come up with a contingency plan for every single possible outcome of sex.

That’s why I agree that your reasoning, while perfectly rational, may be a bit too “intense,” and I see no need to share it with every guy you’re thinking of having sex with. If you’re on a date, and you’re feeling this guy has the potential, may I suggest a simple, “I guess I’ve just been waiting for the right guy, and I still haven’t found him. Who knows, maybe he’s sitting in this room right now….”

Say that with a wink and a smile, and I promise it will be explanation enough for the guy. If it isn’t, then he’s probably not the one, anyway.

If you’d like to ask the guys a question, email me at wendy@dearwendy.com with “His Take” in the subject line and I’ll pass your question along to them.


  1. kerrycontrary says:

    I think all of the men’s advice is great. While abstinence is the only 100% foolproof birth control, the chance of you getting pregnant while using birth control pills and condoms is slim to none. Like .003% probably. And you probably take plenty of higher risks in your life every day with your safety by crossing the street, driving a car, etc…But if you’re only going to have sex with someone that you’re willing to have a baby with (and presumably marry), then you are going to be hard pressed to find someone to have sex with (unless you are looking in more religious or conservative social circles). Like Dennis said, you can’t know if someone is going to be a good father or stick around until it actually happens. I mean I can’t imagine if every time I was going to have sex with someone new I said “are you willing to have a child with me?” I mean that totally kills the mood, and if we’re properly using BC, it’s not a necessary question. People get accidentally pregnant all the time but most of those people aren’t getting pregnant when properly using birth control. They either don’t use any birth control and can’t believe it only takes one time, they use condoms improperly, they are on anti-biotics with their birth control pills and don’t use a backup method, they skip pills, etc….I mean your phobia of an unplanned pregnancy is causing you to miss out on one of life’s greatest events!

  2. Have you done other sex-like things without having intercourse? Because I think there’s a big difference between “Hi yes I’m a virgin and by that I mean I’ve never made out with anybody” (wattup, Christy circa 2011) and “Hi yes I’m a virgin but really only in that technical, everything but intercourse, sense.” Because I think if it’s the first one (or a version thereof) then you’re kind of fooling yourself because you weren’t gonna get pregnant from a blowjob. (I kind of think you’re fooling yourself even if it’s the second version, because the implant is 99% effective, and is in fact more effective than getting your tubes tied. Don’t ask me how that’s true.)

    1. kerrycontrary says:

      Christy, you’re right. I forgot to mention this above, but my good friend just had an experience with a guy who was a virgin and they started having sex and he freaked out and explained it (we’re 26-27). He had done everything else and was good at it too. And she liked him, and was willing to work with him on it, but she had wished he had brought it up because she felt bad. So the LW shouldn’t feel bad about bringing it up. I don’t think you need to go in THAT much detail about the pregnancy-fear, you could just say “it just hasn’t happened yet”. They don’t need to know the reason.

      1. Right, I’m incapable of keeping anything from gf (even when I intend to) so the idea of not telling her just wouldn’t have worked for me.

    2. iuds are also more effective then getting your tubes tied! so weird.

  3. PumpkinLatte says:

    All good advice, and I personally like Diablo’s remark about being vulnerable. LW, I waited until I was 25 to have sex, for various reasons – mostly that I was super awkward. A few guys were like “nope!” when I told them I was a virgin and most of the others did not want to take my virginity because they (wrongly) assumed that it meant a great deal to me and that sex was going to make the relationship more serious than it was because of my inexperience. You don’t have to disclose your sexual history if you don’t want to. If it’s a casual thing, it’s definitely okay for you to say that you don’t have much experience with sex and let your partner interpret that as he will. If it’s the next step in a more serious relationship, the right guy will be a true partner in this with you. Meaning, he will respect you and not belittle you or whatever you’re fearing will happen.

    On a more practical note, and I’m sure you’ve already looked into this, but lube is your friend. Squirt out as much as you think you’ll need – and then squirt out some more, seriously. If you need a recommendation, Babeland sells a nice, thick natural lube under their own name.

    1. +1. When I first had sex with gf, she knew I was a virgin, and she certainly wasn’t belittling or anything like that. Like, she knew it was a big deal for me, but SHE isn’t the one who made it a big deal. She was careful to respect my boundaries and to make sure I was happy with how things were progressing.

      And honestly, I don’t even remember our first time having sex, other than that I was VERY excited about it and it was a lot of fun. Seriously, I can estimate what month it was based on when we started dating, and I know it was at her apartment. But it wasn’t like “I remember every minute of this,” because it just made sense to have sex at that point.

      1. kerrycontrary says:

        I like barely remember my first time either. As you said, it was a natural escalation of experiences. It’s really not the big deal people make it out to be (at least it wasn’t for me)

      2. Why the thumbs down, people? I didn’t feel like my first time was a big deal either.

      3. kerrycontrary says:

        I apparently have a nemesis on this site. Who cares! 🙂

      4. No, you apparently have 2 nemeses (nemesii?)

      5. PumpkinLatte says:

        Yep, it really wasn’t a big deal for me either. I do remember my first time mostly because I was thinking “wow, this kind of sucks” and then I cried after because it sucked so bad and I was disappointed and slightly drunk. True story.

      6. Avatar photo GatorGirl says:

        My first time was a big deal. I know what month it was, and could probably pin point the day if I had a calendar. And it was 12 years ago (damn!). So, I think it can go either way (BFD or not at all) and a million points in between.

      7. Avatar photo LadyinPurpleNotRed says:

        The only reason I know exactly when the first time I had sex was, is because I saw Tom Petty and the Heartbreakers the next night as a high school graduation present from my parents.

      8. Mine was Labor Day weekend my freshman year of college. The only reason I remember is because it was my first weekend of college!

      9. kerrycontrary says:

        Love it. Every first weekend of college I always ask my fiance “how many people do you think lost their virginity this week”. I lost mine in college the weekend of a very important football game. How cliche.

      10. yeah, I do not remember the date of mine at all, which is weird because I tend to remember dates without even trying? All I know is that is was the end of my freshman year of high school (like May, June?)

  4. Painted_lady says:

    Dennis, I think this is the first time I’ve ever said this, but I love your point about the potential-good-father line of thinking. LW seems to want some kind of guarantee that she’s making the right decision, and there are really, really no guarantees in life. And though I doubt (I hope not) that LW would use the “You seem like a good father” line, holy shit if some dude said that to me I would run screaming away because WHAT?! ETA: If some guy said I’d be a good father, I would run for other, more obvious reasons. I mean if some guy said I would be a good mother.

    Diablo, you touched on why I waited till I was 23 to have the kind of sex that could lead to a baby. I felt like waiting gave me some control over what happened in my relationships, and it absolutely did not. LW, I feel like some of this “don’t want a baby” stuff is code for “want to do everything I can to make sure he won’t leave me.” Not like you would trap this guy with a baby, but that a guy who would be a good father isn’t going to leave you. And aside from really not being able to know that ever, you’re also depriving yourself of the leap of faith that is, like Diablo said, making yourself vulnerable. Can you be hurt by someone you don’t have sex with? Of course! But if you’re using no sex as a means to protect yourself like I did, you’re still getting hurt, but you’re not ever really relinquishing control. And this could be anything – no sex, keeping parts of yourself secret out of fear, never being completely naked in front of a partner…if these decisions are made out of fear of getting hurt, you’re only hurting yourself.

    1. In my case, i definitely wanted to wait until I could find a girl who liked jazz. Hahahahahaha, just kidding! Actually, the year before I lost my v-card, I took a girl to a jazz concert (which 19 yo me thought might impress her with my highly developed sophistication). In retrospect, i totally could have given it up that night, but I lacked the nerve to make the move. Totally friendzoned, but a great lesson learned. The Lesson: like, DO something, stud-puppet!

  5. I am with Diablo all the way on this one—absolutely love the first paragraph, especially, & think it’s dead-on.

    LW, it’s not that your reasoning is “too intense”… it’s just, too bizarre? Pregnancy is preventable, not an unavoidable side effect of sex. “Scientifically speaking”, as you say, your logic is wrong. I would maybe explore why you’ve never wavered from this (il)logic your whole life. As for the dudes—yeah, some will definitely be thrown off. Especially pro-choice, liberal ones such as yourself. It’s not an impossible situation to navigate, but you’ve sort of developed a catch-22 (?) for yourself? (Guys who won’t be fazed by it will also be on the opposite politcal/religious spectrum as you, & guys who will are likely the ones who are better matches…)

    1. lets_be_honest says:

      I wonder if this is a normal thing for people exposed to single moms (exposed, lol, like its a disease). I just say that because between this LW and all my sisters, it seems to be a common thing.

      1. Avatar photo GatorGirl says:

        Anecdotally, I think being hyper conscious about unplanned pregnancy can be related to having a single mom. I grew up with a single mom (until I was 8) but I’ve always been very careful about not getting pregs. But then there are countless reports of the cyclical nature of teen moms and/or single moms so, idk.

      2. lets_be_honest says:

        Yea, good point. It is really weird that there’s that connection between if you have a single mom, I guess odds are higher for you to be one too (or is that teen moms?) yet there are people like you who are extra careful bc of your mom.

      3. Avatar photo GatorGirl says:

        With little real knowledge about this- I think a lot of it also has to do with the socio-economic environment of the kid. Like my mom came from a line of single and/or teen moms (her mom, grandmom, etc) and they all lived in the same town, same income bracket, same schools etc- it was all cyclical. My mom married my step dad when I was 8 and we moved up economically, moved towns and school districts, and the cycle stopped.

        I have a cousin who is 6 months older than me (her mom is my mom’s step sister), who stayed in the same town, same schools, same income bracket, and she repeated the cycle. It’s all very interesting to me (and anecdotal…so no one be a jerk please.)

      4. lets_be_honest says:

        It is interesting, but kind of more sad than interesting.

      5. Avatar photo LlamaPajamas says:

        I can see being extra careful – maybe using condoms as well as birth control pills or an IUD. But not having sex at all solely because you’re afraid of pregnancy?

      6. Avatar photo GatorGirl says:

        Oh, I had plenty of sex. haha. Just was diligent about BC. I think LW is a little extreme with avoiding sex all together, but what ever floats her boat.

      7. Not all single moms start off as single. My parents were HS sweethearts. My mom became a single mom because after they divorced, my dad ceased all contact and left the state.

      8. lets_be_honest says:

        Definitely a good thing for the LW to hear/be reminded of, but I wasn’t saying otherwise.
        Did you find yourself more fearful of having babies and then being alone? I think between me being single when I got pregnant and my mom, who became a single parent the same way your’s did, my sisters are extra scared of having kids?

      9. I don’t want to have children ever and that has more to do with my disability than whether I’ll be a single parent. But when I was younger, like 19-20, I sort of wanted to get pregnant because I was lonely and thought having a baby would make me less lonely.

      10. lets_be_honest says:

        I hope you are less lonely now 🙂

      11. I definitely am. I’ve grown and matured over the past while. I am now 28 with a lot more to my life.

    2. Avatar photo LlamaPajamas says:

      I agree with all the guys (especially Dennis, hooray!) and Fabelle. And I think that something seems off, like maybe there’s something really important that the LW is leaving out. Because “scientifically speaking”, this is pretty extreme.

    3. The fact is that pregnancy is a possible consequence of sex. It amazes me the number of people who have sex and are shocked they are suddenly pregnant. Where did they think babies come from?

      I’ve had a number of friends become pregnant despite using birth control. They took the pill as directed and avoided antibiotics. Still, they became pregnant and are struggling to survive. Sometimes these things happen. If the remote possibility of becoming pregnant absolutely terrifies you, then having sex is probably not a good idea. You need to be able to accept and take responsibility for anything that happens. It’s part of being a responsible adult. Too many people treat sex like a handshake. It’s quite sad really, in my opinion. Sex is a big responsibility that shouldn’t be taken lightly. One of my good friends now has HIV. Her boyfriend used a condom and wasn’t aware he even had HIV.

      What this 28-year-old virgin should do is make it clear from the beginning that she is looking for a long-term relationship. As for her virginity status, she can say that she’s inexperienced and leave it at that if she wants. The guy will most likely pry for more information about her specific level of experience at which point he’ll probably ask if she’s a virgin. It’s best to be direct and honest about it. If a guy walks away because a girl is a virgin, he probably wasn’t serious enough about her anyway.

  6. Bittergaymark says:

    All these takes are solid. But Diablo wins this round — hands down.

    1. Lily in NYC says:

      I came here to write the same exact thing.

    2. I think Diablo’s been on a roll for the last few weeks.

  7. lets_be_honest says:

    Wow and wow. Crazy good advice from the guys who hit on every point I thought while reading this. So now I have nothing to say…other than Brian’s p.s. makes me want Addie to marry him a little more than I already wanted.

  8. i like that all of the guys brought up being too far in the “what happens if i accidentally get pregnant?” direction. i mean its all about balance, and i say this as someone who has had constant pregnancy fear for years, thought i was pregnant every month in high school, and constantly asked JK if i was pregnant after my boyfriend and i stopped using condoms. but… we cant live in constant, crippling fear of life in that way, and sex is actually a huge part of life in general, especially in america. its just like you cant live in constant, crippling fear of flying, or being outside your house, or of dogs, or whatever. and by constant crippling i mean fear that will cause inaction to the point that you dont get to live your life the way you want to. so what i think you need is a plan. you say you want to have sex now. so, what is your plan? is your plan to only have sex if you are willing to have a baby with that guy? if so, put that in action. if your plan is no babies, but sex now, then figure that out. get on birth control. carry condoms, ect. and then, have another plan- what if the birth control fails? ect. life is life, and no matter what plans we make and what we do, we can never predict anything 100%. but, having a game plan is a good thing. it will hopefully bring you some peace. and, think about it this way- worst case senario, you have sex and get pregnant and the guy is a loser and leaves you. what about the worst case scenario now? you are ready to have sex but are having these “issues” with explaining why and finding a guy to do it with. like, there are problems no matter where you look, that is how life works.
    anyone who would scoff at your sexual history is ridiculous and you dont want to be dating them or having sex with them. think of this in the opposite direction- what if you had 10, 20, 30 sexual partners (is that a lot? i dont even know. its all relative, LW!) and someone scoffed at that? that is equally wrong. so to me, that certain part of your issue is a non-issue. you will weed out assholes that way.

  9. Avatar photo veritek33 says:

    Okay, I’ll put some of my business on the street here. I lost my virginity at 26.
    I was also worried about becoming pregnant and getting diseases and such since I grew up with a social worker/juvenile officer mother.
    It was also a combo of lack of self esteem on my part and just not finding a guy I wanted to have sex with until my mid twenties.
    And then I met my ex. And things just clicked. And I agonized about how to tell him I’d “never done this before.” We were making out pretty hot and heavy and I knew where things were going and so I just told him I needed him to know something. I WAS SHAKING LIKE A LEAF THE WHOLE TIME. And I told him. And to his credit, he took it like a champ. He said “Oh, that’s it? I thought you were gonna tell me you had herpes or something. I can handle you being a virgin.” And we had sex, and it was good.

    He turned out to be a douchebag later, but honestly, to him it didn’t matter at the time because he liked me and i liked him. So I’d say with the right person, it won’t matter. They may not marry you and have babies with you, but losing your virginity is not this colossal be all end all event. Sex is fun, and @diablo is right, people have sex all the time and don’t have babies. The ex and I had sex for two years and never got pregnant. Use two forms of birth control, and have fun.
    Stop worrying so much and trying to plan out every little detail of your future.

    1. Avatar photo veritek33 says:

      I got my first thumbs down!! I feel like I’ve finally arrived…..

  10. lets_be_honest says:

    Oh LW should read the sex scene from the Fault in Our Stars that we talked about yesterday!

    1. LALALALALA I can’t hear you.

      1. lets_be_honest says:

        CRAP! I’m sorry. This is exactly why no one can tell me secrets.

  11. Avatar photo lemongrass says:

    I’m with Diablo here. I don’t think your issue is your virginity it’s that you don’t want to put yourself on a limb and risk anything. But no risk, no reward.

  12. applescruffs says:

    I have a friend who is…I think a 26 year old version at this point, for a lot of the same reasons. She won’t go on hormonal birth control because she believes it caused her mother’s cancer, she won’t use condoms (!!!) because when she loves someone she doesn’t want any barrier between them, she won’t get an IUD…well, I don’t know why she won’t get an IUD. But really, I think she’s so afraid to risk getting hurt by a guy leaving, a breakup, that she won’t date anyone or have sex unless it’s a “sure thing” that this will work out. And of course, in life there are no sure things. You can’t protect yourself from everything. So enjoy the ride, smile through the pain, and know that eventually, hopefully, things will work out just fine.

  13. Avatar photo Addie Pray says:

    Oh hi hi hi hi hi hi, boys. And Brian.

    1. Brian Fairbanks says:

      Hi. Sorry I’m late.

  14. Avatar photo Guy Friday says:

    I really like Dennis’s advice, particularly the part about the “fantastic father” counter-point. I don’t think there’s anything wrong with wanting to wait until you have the framework of a financial plan in place just to be safe, but I think waiting until you meet someone who could be a fantastic father — aside from the points Dennis made — is kind of like wanting to wait to date someone until you know they’re up for engagement and marriage: it’s a lot of intensity to put in right away.

    LW, I don’t think you’re wrong to wait until marriage or a long-term commitment or whatever to have sex if that’s what you want to do, and I don’t think being a virgin at 28 is something that guys who aren’t just looking to get some are going to particularly care about. I mean, it’s like discussing everything else sexual: different people have tried different things at different times, and while some men might want a woman who has done what they liked before most men, in my experience, don’t care that much. In fact, I think — and I may be wrong about this — that ironically it’s actually MORE acceptable to “wait until marriage” or to do something similar than it was 50 years ago. I think that much in the way that people see being a housewife rather than a bread-winner as a conscious choice a woman can make, so too do they say a woman being a virgin rather than sexually active. Besides, it’s been pretty well pointed-out by now that it’s not like you’re really doing this out of fear; you’ve been holding off to get your life in order while dating and being social, and it’s not like you’re hiding in your dark apartment crying quietly while stroking your 17 cats or something 🙂

    (As an aside — and I apologize if this makes me sound sketchy — I think that a lot of guys might actually consider you being a virgin to be a bigger turn-on than not. I mean, to be the first guy you trust enough / want enough to give up your virginity to is a HUGE ego boost, you know?)

  15. Avatar photo Addie Pray says:

    LW, I know you’re nervous about this and worried about what men will say and what you should say back and all that jazz, but I don’t think you owe any explanation. Whether you’ve done it zero times or with only one partner or with tons of dudes, you don’t have to divulge that information at all. And as for your reasons for not having sex until now? It’s no one’s business but yours (and ours – of course – because we love being nosy! ok, I love it, and iwanna loves it); you don’t need to explain yourself at all.

    1. Avatar photo iwannatalktosampson says:

      It’s true. Dish. I love everyone’s reasons for having the sex, not having the sex, having the weird sex, and the upside down sex, and the sex in groups, and all of it.

      1. Avatar photo Addie Pray says:

        a, I agree – i love hearing people’s reasons but…. b, LW, seriously, as to your reason for not having sex until now? maybe it’s a silly reason or a serious reason or medical reason or religious reason or maybe it’s a reason that has changed over time or maybe it’s a handful of reasons or maybe you have no reason at all – you really do not owe anyone any explanation.

      2. Avatar photo iwannatalktosampson says:

        Yeah really. And if a guy wants to hold being a virgin against you (Oh how my grandmother would laugh at the irony) then fuck them. They probably suck in bed anyways.

      3. Avatar photo call-me-hobo says:

        Of course, don’t LITERALLY fuck them. Wait for someone who is awesome and doesn’t care about the whole virgin thing but does care about you and then fuck THEM.

      4. Avatar photo iwannatalktosampson says:

        Bhahah. Thank you. You’re spirit is appreciated.

      5. Avatar photo Addie Pray says:

        haha i love hobo so hard! you guys, i’ve met her in person and she is just as delightful as you’d expect by her comments!

      6. Avatar photo call-me-hobo says:

        D’awwww. I love YOU so hard!

  16. My husband lost his virginity in his late 20s. First of all, it’s something I never would have known about him. I think a lot of people fear that stereotype of still being a virgin and living in their mom’s basement or being an outcast of society. And LW, from everything you write, you sound like a well adjusted, normal person. The right person will never judge you for how many or how few partners you’ve had. And before I met my husband, I did think I would care about someone with very little experience, but once it actually happened, I didn’t care at all.
    He also had a deep fear of pregnancy and he felt a lack of control with that because as much as there are things he can do to prevent pregnancy, it is still more in my control/he can’t tell me what to do with my body. He knows lots of people where he grew up that got accidentally pregnant in their teens or 20s, but that doesn’t mean it would happen to him. Pregnancy is preventable. And this is a little embarrassing to admit, but when we were dating, we used 4 (!) types of birth control. He’s much more comfortable now with using less, but that’s what it took for him to be comfortable with releasing his anxiety and fully enjoying sex at first. He also used to have trouble being completely naked in front of me. And sex can be really vulnerable. If you don’t want to be vulnerable, sure you can say “I won’t have sex”, or “I won’t date”, “I won’t go to social events”, and it goes on and on, but why miss out on good things and not take chances because you’re scared of a potentially bad thing? The good outweighs the bad here. Even if you do have a bad sexual experience, I’m sure you will go on to have many more positive ones. You ask if being a virgin at 28 will scare guys off. Will it scare off some? Maybe. But there are plenty of men who will not be scared by that. Don’t be scared or embarrassed about it yourself. Be confident. People wait to have sex for all sorts of reasons. The right person will always respect your choices and it won’t be too intense. I think everyone has something that they fear a partner will care about in a relationship, but it ends up not being a big deal.

    1. can i just ask- what 4 types? im trying to envision this (not literally but…) … like, the pill, condoms, diaphram, and… spermicide? lol

      1. Haha oh it’s fine. We used condoms, spermicide, withdrawal, and I was on the Depo shot. Definitely overprepared.

  17. findingtheearth says:

    As a single mom, I can understand hesitancy to get into a relationship and have sex. I have not dated since my daughter was born, and don’t plan on it until I meet someone who is willing to wait and take it slow. I think it is good to be honest with your intentions and where you are at, and I think if you meet someone who respects you, your choices, and your body, it won’t be so scary.

  18. LW, I feel you! I’ve dated plenty of guys who have been respectful of me being a virgin but at the same time I’ve had weird experiences because of it. Like the one guy who was oddly fascinated by my virginity — I think he fantasized about taking it? Super creepy and now it gives me the heebie jeebies. Then there was the guy who was like “well, when you say no you REALLY mean yes!” Ugh. Creeptastic.

    So weed out the creepers. Keep your standards high. I would be open about being a virgin but you don’t owe an explanation to anyone as to why and what got you here. There are plenty of respectful guys who will understand and won’t push you for an explanation. Good luck!

    1. I get that my choice is not the popular choice, but I’m curious as to what the thumbs downers have to say.

  19. LittleGlassGirl says:

    I was a virgin until 21, when I lost it to my 28yr old fiancé. To him and others I had dated and revealed my V-card status to, it was a MUCH bigger turn on than it was a deterrent. With some instances of it being TOO big of a turn on to some guys, which seriously creeped me out. So be careful of those types.

    It really comes down to the type of guy really. And if you don’t mind losing it casually or if you prefer to be in a relationship first. Decide that first. Casual sex guys will probably be the most freaked out by it, since they think it will mean serious commitment afterwards or something. But if you act like it’s genuinely not a big deal, then they probably will too.

    But if it IS a big deal for you (it was for me), then I’d say your best bet is a relationship guy (a guy who is actively looking for a relationship). Because then you know he really is interested in knowing you beyond the sex part, and your reasons for waiting to lose your V-card won’t seem as “intense”.

    My fiancé was way more nervous than I was the first time, he was shaking and everything lol. I had never even kissed another guy before, so just taking my clothes off was a big deal for me. It was a super vulnerable and intimate act for me. Also it really HURT, and there was quite a bit of blood (nobody told me this! I had to ask my fiancé, “is this normal?!” and he just said “yes, my mom’s a nurse and told me & my brother about this stuff”. Then we laughed and he held me and we did it again lol).

    ANYWAY, my point is I am very glad I waited and didn’t just casually lose it. It would’ve been awful with someone I hardly knew. But that’s me, not you. So definitely decide how big of a deal it is to you. Aside from the whole potential baby thing. Like others have said, that’s pretty easily avoidable. Decide if this is really important to you or not, the guy you’re with will more than likely handle it whichever way you do.

    1. Wendy (not Wendy) says:

      Oh, but it’s WAY different when you’ve “waited” until you’re all of 21, vs. late twenties and beyond. The situations (as far as the pertinent question–how will guys react?–goes) aren’t comparable.

      1. LittleGlassGirl says:

        Well the guys ages are comparable, mid to late 20’s, which I’m assuming she’ll be dating in her age group (late 20s). She’s more concerned about what they will think/react etc. But really that’s beside the point. It comes down to the type of guy, his age doesn’t matter and neither does hers. So I think she should get to know someone for a while before even going there. A guy that’s interested beyond sex would far more likely be open to her reasons.

        Also, may I ask why you put “waited” in quotations? Does being “all of 21” and not engaging in any sexual relations until I found the guy I was going to marry not count as “waiting”? I didn’t know there were qualifications to it.

      2. Wendy (not Wendy) says:

        I know your advice was well-meant and I was more snarky than I should have been. I just think the differences are important. There’s judgment from society (on a personal level and a general level both) for people who don’t have sex until later in life compared to people who have sex for the first time when they’re 21. They don’t make deprecating comedies called “The 21-Year-Old Virgin”. Again, I know you don’t mean to, but I think to compare the two trivializes the LW’s worries, which are valid. To many people, a 21-year-old virgin is a turn-on, as you note. A 28-year-old virgin is a freakshow at worst, a cause for skepticism among many.

      3. LittleGlassGirl says:

        Well they don’t make deprecating comedies called “The 28-Year-Old Virgin” either. (It was 40 year old, right? Now that I agree is a huge difference). You’ll probably never see a movie making fun of a woman who’s a virgin at any age. I think there’s far more judgement on a GUY in today’s society to still be a virgin at that age (which is awful), not really for a woman. Thus the stupid reason why guys feel they need to up their “number” & women feel they need to lower theirs.

        I think the comparison I made is appropriate (even tho I don’t believe the ages to be a significant factor at all) and perhaps you may be projecting too much doom-and-gloom on this than there needs to be. A freak show, really? If there really are guys out there who would think that of her, then good riddance. She deserves a man of much higher quality. Because whether she was 21 or 28, the guy is a waste of time nonetheless if he’s going to cast so much judgment on her for that, of all things. Which again, brings us back to type of guy being important, not age. She’ll just weed them out quicker.

      4. Wendy (not Wendy) says:

        Look, we’re on the same page about how a guy who’s worth it won’t really care (though some guys who ARE worth it will still have a moment of doubt: see the guys’ responses above), but I suggest you don’t deny there’s a significant stigma about something that you never experienced when other people, who have (the LW, a recent xojane columnist, the author of Latter-Day Virgin), will tell you there is. Should there be anxiety about it? No, of course not. But unfortunately, how a guy will react is a valid concern, and even if he turns out to be a jerk who’s not worth it or someone who’s immature and can’t handle it, it’s still going to hurt in the moment.

      5. You come off as closed minded and kind of judge-y here. There are PLENTY of reasons to stay a virgin until later in life.

      6. Wendy (not Wendy) says:

        Wait, I come off as closed-minded and judgey? I’m not sure how I gave off that impression. For the record, depending on what standard you use, I was in my thirties. I KNOW the stigma. And I know how complex it is. And I’ve seen broken hearts of evangelical Christian women whose sisters and mothers were cruel to them after they had sex without being married at, say, 25, because those sisters and mothers had waited like they were taught… until they got married at 20 or 21. That’s why I’m a bit touchy on the subject.

      7. LittleGlassGirl says:

        First of all, that sounds like it has way more to do with those mothers & sisters being angry that the woman was not true to her own beliefs because she got tired of waiting. Anyone would be angry at someone who was not true to what they themselves believed. However, cruelty should never have been the answer, & that is unfortunate.

        So, especially given your previous snarky comments, you’re saying “waiting” until 21 is SO much easier & doesn’t even count like, say, waiting til 25? Or 28? That is where you come off as judge-y. Discrediting what someone has done, which is not even your place to do so, over a few years difference. As if those who wait LONGER are the only ones who actually “count”, which is all very ridiculous. Just because someone found their husband a few years sooner than another does not mean it was “easier” for them to wait. Especially when most people around you are losing it at 17/high school.

        It is always admirable if someone is true to their beliefs, whether that be at 21 or 28. For you to discredit that because they didn’t have to wait as many years as, say, you, is appalling.

      8. Avatar photo GatorGirl says:

        I really don’t think she is trying to discredit anyone’s experience…just saying they are different and not really comparable. I don’t get why that is such a terrible thing to say. Not Wendy isn’t saying your experience “doesn’t count” just that it’s different than hers and this LW.

      9. LittleGlassGirl says:

        Perhaps if she hadn’t put “waited” in quotations when replying to my post, along with the comment “waiting until all of 21”, and saying “those mothers & sisters had waited like they were taught…until they got married at 20-21”, I could agree with you GatorGirl. To me, it appears she is in fact discrediting others experiences.

  20. Sobriquet says:

    Don’t wait until you have your clothes off to bring up the fact that you’re a virgin. Don’t belittle your very serious reasoning for waiting, either. This is what I did: I was 19 and had a few intense make out sessions with the guy I was dating. He wanted to move forward and I told him I’d never gone that far before because it was too painful. He made me feel normal, understood my concern and let me know that we could ease into as painlessly as possible. It took about 4 intensely painful attempts until we finally had sex. And it was still kinda painful, ha, but it’s not anymore! So if I were you and I’d found a guy I wanted to sleep with, I’d be honest. Say, “Up until now I’ve been a little terrified at the consequence of sex, but recently I’ve had a change of heart” and go from there. It won’t be a big deal to a mature man who really likes you. It really won’t.

    Am I the only person who had extremely painful- needles and knives stabbing me- like sex early on? Most of my friends didn’t even feel it.

    1. Avatar photo GatorGirl says:

      You’re not alone. My first time was super painful (like tears and lots of bleeding) and even now if it’s been a week or ten days I have some initial discomfort/tearing (TMI?? Sorry). (And no, it’s not a lube issue. That’s well addressed.)

    2. LittleGlassGirl says:

      Definitely not alone. It was very painful for me too, very sharp piercing pain, & a lot of blood. It took a couple hours, with long breaks in between trying, before he could “get in” (sorry if TMI). I was completely confused and thought there was something wrong with me lol. In movies, books, friends experiences etc it’s super easy, like no pain & he just glides in. So not the case for me.

      But after the first few times, it became easier & easier, & far more enjoyable. Until it was awesome. Lol

  21. Sobriquet says:

    Yeah, if it’s been more than a few days I have to tell my fiancé to ease into it slowly (tmi!) because it will hurt at first. I didn’t bleed when I lost my virginity, but sometimes I’ll bleed when sex is rough or a position stretches/tears me.

  22. Avatar photo fast eddie says:

    I’m surprised that nobody mentioned that the hymen can be surgically removed which has got to be easier then a guys blunt instrument of invasion. Dildos would be another option.

    1. simonthegrey says:

      I lost mine to the speculum at the gyno. Tear, cramp, small bleed, over with.

  23. simonthegrey says:

    All right, lived experience. I was a 28 year old virgin when I met my now-husband. He was not a virgin, though he had only had one long-term girlfriend before me and only 2 partners total. I brought it up in one of the second or third long conversations we had together, because we were telling each other things about ourselves. Not only was I a virgin, I had never even kissed another person before. I wasn’t a prude, and I wasn’t overly religious; I had identified as asexual before then, completely uninterested in sex. He thought it was a little strange, but he didn’t see it as a challenge or some kind of prize. We also didn’t start having sex right then; we were together for quite a while before we “went all the way” though we had done basically everything else by then.

    Basically, don’t worry about it; when it happens, it happens. As long as you take precautions and don’t believe the first time will be amazing, or don’t build it up in your mind to something it isn’t, just let it happen.

  24. It wouldn’t bother me. I know several people who are 26-40 (yes 40 no judgement people), and while I lost it at 18…it is kinda nice that someone feels comfortable enough to admit that to you. You should be proud of their choice…not judgemental.

  25. 32-Year-Old (Non)-Virgin says:

    While grabbing a drink last night, my friend stopped me in the middle of a conversation, leaned in, and quietly asked if I had ever written to a blog called “Dear Wendy” for relationship advice. I said, “No,” which I thought was the truth.

    She went on to tell me about a question that sounded a lot like my story and my writing style. She described the post to me and suddenly I recalled sitting at my kitchen table, Googling “28-year-old virgin” and “virgin stigmas,” stumbling onto this website, and writing an e-mail to Wendy.

    I remember being excited to hear back from her when she told me she’d pass my question along to a group of men, and disappointed that I never heard back. Then obviously, I forgot about it and moved on. In hind sight, I should have checked the blog rather than my e-mail for the response, because lo and behold, the answers have been here all along!

    I took some time to re-read my question, all the guys’ answers, and every single comment. I appreciate all of your thoughts and ideas, but I’m also glad I only just read them—this was something I had to sort out on my own.

    I am surprised I didn’t mention that, while I’m not religious, I did attend Catholic schools with a very strict “abstinence only” “sex-ed” program. Almost all of my friends from high school didn’t have sex until their mid-late 20’s–thanks a lot, Pam Stenzel. None of us knew how to talk about our perceived lack of experience. I had a particularly hard time, given my home life.

    Many people here seemed interested in the nuances of my decision, but that wasn’t really what I was asking about. I just wanted to know how to talk about it with guys and if they’d think I was weird. (That said, I get it—I would want all the details, too, if I were in your shoes).

    I wrote this at the turning point in my dating life and my career. I had recently quit a stable job to start a business and simultaneously made a conscious decision to actively date. It was all overwhelming and exciting. In college and grad school, I met guys through activities, travel groups, and friends. At 28, I started on-line dating and chatting up strangers who I found attractive.

    The virgin thing kind of sorted itself out with practice. With some trial and error, I rewrote my narrative surrounding sex. Ultimately, instead of thinking of it as a scarlet letter (pardon the irony), I started to think of it as anecdotal. I told several guys—both friends and guys I dated—and none of them flinched. No one fetishize it. No one ran. By the time I lost the last shred of my virginity, it didn’t seem like a big deal anymore.

    It’s funny that this resurfaced now: I have been reflecting on how my attitudes toward dating, sex and intimacy have changed over the past four years, how much I’ve learned from dating, and oddly enough, how all of these lessons parallel those I’ve learned while starting a business (also for the past four years). I even started writing a collection of short, anecdotal stories illustrating the common denominators.

    Finding this has been like discovering a time capsule you forgot you buried, just when you need whatever is inside. Thank you for all of your thoughts and ideas!

    1. I checked my email archives and you’re right: I never did send a follow-up with you with a link to your posted letter (and answers). I’m so sorry about that. It’s always been my practice to send links to LWs when I post their letters, so it was an oversight that I neglected to do that for you.

      I’m glad you’re doing well and enjoyed the “time capsule” aspect of finding this column all these years after writing in. Best wishes to you!

  26. Most men would be delighted to be able to marry a virgin. You are very desireable and saving yourself will make your marriage so much better than women who bring baggage with them.

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