Your Turn: “Should I Tell Him I Was a Virgin?”

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

I was a late bloomer and recently lost my virginity at 23. It was never something I was ashamed of, but I definitely had some insecurities about it. I ended up losing it to one of my best guy friends, who is now my boyfriend, but I never told him he was my first. I know that my sexual history, or lack thereof, is not necessarily any of his business, but sometimes I wonder if I should have or still should tell him. — Late Bloomer


  1. This is not about what you *should* do. It’s about what you want to do. Do you want to tell him? Do you think that it might be a good idea to share this with someone you hope to continue an intimate relationship with? If I were you, this is something I’d want to share with someone I was so close to. Has he talked to you about whether he was a virgin before you?

  2. applescruff says:

    It’s absolutely up to you if you want to share this information with your boyfriend or not. I tend to believe that my sexual history (or my partner’s) before our relationship is irrelevant, aside from the “have you been tested” question. If you would like to tell your boyfriend he was your first, then I think you should absolutely do what you’re comfortable with. Like HmC said, it’s not a matter of if you SHOULD tell him, but if you want to.

  3. I don’t think you’re obligated to tell him. But if you feel comfortable doing so, and know that he cares about you and won’t judge you, it’s entirely up to your discretion.

    If he cares about you, it won’t be a huge deal. And he will probably feel good that you trusted him enough just to tell him. I don’t think he NEEDS to know. But I say go for it!

  4. When I was with my ex, he told me after we’d already been together for about 3 months that I was his first. I was completely shocked and a little upset that he hadn’t told me before. My thinking at the time was, if I knew I never would have slept with him. But by that point I was already happy in our relationship. It didn’t change anything and I got over it.

    Like HmC said above, only tell him if you want to. But if you do, I don’t think you need to worry much about what his reaction will be.

    1. I am curious, why wouldn’t you have slept with him if you had known? I understand if that is personal, I just found the reaction interesting and a bit perplexing…

    2. I see you talk more about this below, I think I understand a bit more now. I also was someone’s first, but I had a different reaction. It is interesting to read how women feel about this situation.

      1. Being someone’s first would feel like such a big responsibility, even though I guess it’s really not… After I found out, I was like oh no! What should I have done differently? Was it ok for him? Why’d he pick me?? Did he feel pressured? Just a lot of questions going on in my head and it honestly made ME feel insecure.

      2. I can completely see where you are coming from, it makes total sense. I think when I was his first, I was still so inexperienced (though not a virgin anymore), it sort of felt like we were both new at it.

      3. That’s the other thing… our first time was terrible. Afterward I kept thinking it was all my fault and worrying about what he must think of me… I guess if I’d known beforehand I would have taken things slowly and let him set the pace.

  5. LolaBeans says:

    Agreed, only tell him if you *want* to.
    It won’t change how he feels about you; he might be quite flattered that he is your first.

  6. Personally, I don’t think he needs to know unless it comes up in a relevant conversation. Guys in general are strange about that kind of thing, and telling him after the fact could make things weird. I think a case could be made that you should have told him BEFORE you slept together so that he could make an informed decision and adjusted his game accordingly. I certainly wouldn’t want to be the one to deflower someone, I feel it’s a rather large responsibility, and I would be upset at having that choice taken away.Telling him now might bring you closer together, but he may also feel hurt, maybe a little betrayed, guilty for not trying “make it perfect for your first time”…

    1. I will say, I’ve heard guys be really freaked out by it, but I do think that since they were friends before AND that they’ve since started dating – that any weirdness would probably go away pretty quickly. From what I understand women and men conceptualize and relate to sex in different ways. I think probably he’ll be able to roll with it. Now I think if the roles were reversed, I can totally see a woman being upset about it because we have a far more emotional relationship with sex. (At least from studies I’ve read, my own experiences and talking to menfolk)

      1. @Darlin’ I’m not sure why you got all those purple thumbs… I agree with you. When my ex told me I was his first, all I could think was, OMG I stole his virginity!! It was a little weird. But like I said, I got over it. We were pretty happy for the time that we were together.

      2. I agree that he may freak out about it, but he will probably get over it pretty quickly. I have known guys, however, who broke up with their girlfriends after finding out they were virgins or previously had been. Some were friends before and some not. However, I believe that if a guy uses that as an excuse to break up with you, he wasn’t very invested in the relationship to begin with. I won’t say whether or not to tell him because I don’t know their relationship and it is a highly personal thing. It is completely her choice, I don’t think he needs to know. Although if he asks I would suggest answering honestly (I.e if the numbers come up, not that he would just ask out of the blue)

  7. Also LW, you are still so young have so much life ahead of you to build whatever sexual history you want- to have sex, not have sex, fall in love, get your heart broken, and do what you want with your life. Congratulations on waiting until you were ready to lose your virginity to someone you trusted. Please don’t have insecurities over waiting until you were ready. There are others out there waiting longer than you, until marriage even, and Many MANY others who are not fortunate to have their first times when they are truly ready. Embrace and appreciate what is best for you.

    1. “Congratulations on waiting until you were ready to lose your virginity to someone you trusted.”

      Thank You! I was waiting to read when someone would say this. I think you should be proud that you waited on someone who you thought was worthy of your body and heart. Whether people agree or not, sex with anyone is a serious choice. I am glad to read of someone else who thinks this way.

      If you do decide to tell him, hopefully he is flattered and honored that you waited on someone like him.

  8. Should isn’t a question for us to answer in this situation. There’s no moral reason why you have to. So there isn’t a “should.” It’s entirely up to you and what you are comfortable with. My only fear would be that the guy would freak out. I know when I was in college dating and brought it up, there were basically three college aged male reactions to virginity 1) Sweet! Let me help you with that 2) Eep! Virgin = Crazy Clingy RUN FOR THE HILLS BOYS! and 3) Uhm…your point is?

    Sometimes I was surprised which one ended up which. You definitely bypassed number 1, and you’ve started dating him, so you’ve most likely bypassed number 2 (as in, you didn’t fulfill the stereotype)

  9. sarolabelle says:

    LW, if you want to tell him because it is in your heart to do so and he reacts negatively, then that’s probably not someone you want to be with long term anyway. While it isn’t the same was say “you know, you were the first person to give me a massage,” the reaction he should have shouldn’t be mad, upset, hurt or crazy. It should just be “oh ok” and maybe “I’m glad we got to experience that night together and you enjoyed yourself”

  10. Elizabeth says:

    If he’s one of your best guy friends and now your boyfriend, I’m sure he’s probably got a little clue that you hadn’t dated much before him and that this was a possibility. And congrats establishing the friends thing first. Much better than losing it to some guy in the back of your parents’ van in a church parking lot with the cops swarming because you didn’t want to go to college a virgin, but I digress.

    I feel that eventually in all relationships, the “numbers talk” comes up. Some couples are comfortable talking about it, others decide to focus on the ‘now’ and not the ‘has beens.’ Still others go for the full honesty policy without evaluating if their partner can handle it. I’ve done all three. I am currently with “partner who couldn’t handle it,” and it took a LONG time for him mature past that. He was definitely more experienced than I was, but he was under a misguided opinion about women. That has since changed.

    I would suggest evaluating the situation. You can always say that you’re not very experienced and maybe could we try this…(make it a discussion about your intimacy together rather than focusing on ‘before me’ or ‘virgin’.) Or ask if he’s been tested (please please please do this) and let the conversation roll from there. In the end, it’s your choice; if you feel inclined, go for it. He’s your best friend. You should be able to trust him. If you end up deciding not to right now, then that’s your choice too. As the previous posters said, it’s a ‘want’ not a ‘should.’ Although I would evaluate yourself as well. What are you expecting to hear from him about his history and will it bother you?

    1. What was your partner’s misguided opinion about women???

      1. Elizabeth says:

        Thyme: All the previous women he had been with had lower numbers than I did. He had a hard time reconciling this at first although now it’s a non-issue. I guess he just judged women more harshly than men, as much of the world unfortunately does.

  11. I say…tell him. A good, healthy relationship needs a good foundation. If he is someone you are interested in having a long term relationship with, then you shouldn’t hold anything back. If he really cares for you & also wants a long term relationship, he won’t mind.
    You may say now it’s not his business, & to a certain extent it’s not, but as relationships progress & become more intamite, things get discussed. & if you’re thinking about whether you should tell him or not, it probably means you really don’t want to keep it to yourself, but you’re scared of his reaction.
    Like I said, if he is a good guy & cares for you, he will not care.

  12. margblogger says:

    I think it’s a very personal decision and there is no right or wrong answer. I’m in my mid twenties and just lost my v-card as well, but I told my boyfriend beforehand, because I felt like he had a right to know. (And it would have been pretty obvious for a few reasons if I hadn’t told him.) I’m really glad I told him even though I was incredibly nervous. He handled it like a gentleman, drank a few beers with me, and then we did it. If he hadn’t known, I think it would have been even more awkward for me, but since your boyfriend hasn’t said anything, maybe he did know or suspects and just is too much of a gentlman to say anything. It might help your relationship grow if you let him know sooner rather than later, but that’s just my two cents. Good luck with your decision, I think a lot of the commenters here are on the right track.

  13. caitie_didn't says:

    I was also a late-bloomer in this aspect, and I told my then-boyfriend that I was a virgin beforehand but at literally the last possible second. I’d fooled around with other guys before, so I wasn’t totally clueless and he said he had no idea until I told him. FWIW, he was an absolutely gentleman- so sweet and he took such great care of me. It’s totally your decision to tell him or not, but it might make you feel more comfortable and give you both the opportunity to go as slow as is necessary. A guy who really cares about you will do everything he can to make sure this experience as as good as it can be for you- but that should be the case whether its your first time having sex *ever* or just your first time with a new person.

  14. I think you should tell him. That’s an intimate thing involving both of you–it sounds like it was the start of your romantic relationship or close to it–and will be a special memory throughout your relationship. If I were your boyfriend, I would be hurt if you didn’t tell me, and if it came out months or years later, it would be more than hurt–like you’d been holding out information about our relationship from me.

    If he weren’t your boyfriend, I would agree with all those who said “it’s up to you and what you want”, but since he is… I don’t think this is a good way to start a relationship.

    The first time I had sex with a man (rather than a woman), I was several years older than you and I didn’t tell him it was my first time. The atmosphere was perfect and I was afraid that would change it. I knew he thought I was sexually experienced with men as well as women. Although it was a short-term fling and we both knew that going in, later I decided that I really wanted him to know. I wanted to thank him for making my first time special even without knowing it, and I wanted him to know just how special our few days together had been and that I would always remember him. A few months had passed and he was startled, hurt for a few moments, and actually didn’t quite believe me–I hope he believes me now. A man’s reaction will vary according to personality and situation.

    Now, why WOULDN’T you tell him? If you’re still insecure, I think the best way to get rid of it is tell him and see that he doesn’t think any less of you because you didn’t have sex until you were 23.

  15. Kerrycontrary says:

    yeh I think there is no “should you or shouldn’t you” in this situation. If you want to tell him, I think you should. You are in a happy relationship so he may be a little shocked, but he’ll get over it soon enough. If he’s enough of a jerk to make a big deal out of it then he’s not worth your time anyways. Either way, you aren’t obligated to tell him. Did you ask how many girls he slept with before you had sex? By reading your letter, I would probably say that’s a “no” because your number would’ve come up in this conversation. Do whatever you feel comfortable with, but I think it will turn out fine.

  16. eel avocado says:

    I’ve actually had an experience with this in the past. In my early 20s, a good guy friend and I had sex. We then became “official boyfriend-girlfriend” a few weeks later. After a few weeks of being together, he revealed that I took his virginity. I honestly had no idea! I was a little surprised because he had girlfriends in the past (and he knew what he was doing!), but it didn’t bother me in the least bit. I say, if you want to share this piece of information, go ahead and tell him. My guess is that it won’t be a big deal and you’ll just go ahead with your lives as usual.

  17. Between now and your 25th wedding anniversary this discussion is going to come up. The question is when it will happen. If you aren’t comfortable discussing it, then don’t bring the subject up. If it does come up, just don’t lie about it.

    I suppose the more you wait, the relationship will have grown and it won’t matter anywhere near as much. It’s in the past already. I doubt the guy would freak out because frankly that would be pointless.

  18. DramaQueen224 says:

    I think one of the most important rules in a relationship is don’t lie and don’t mislead. So, if you ever indicated to him that you weren’t a virgin when you first got together, then yes I think you should tell him and apologize for misleading him. Or, if you guys end up discussing first times or what not, I think you should be truthful. However, if it didn’t/doesn’t come up, then I don’t think you need to tell him if you don’t want to. I agree that people fall into different categories about knowing their partner’s past (doesn’t matter at all vs broad strokes vs details) and what matters is where you and your boyfriend decide you want to be.

  19. All I can think about is remembering MY first time and how there’s NO way I could have hidden the fact that it was my first time from the guy.

    I was incredibly nervous, and then it hurt like bloody HELL, even though he took it really slow and gentle because he knew it was my first time. I shudder to think of how much more excrutiatingly painful it would have been if the guy hadn’t known I was a virgin and just started going at it.

    But I guess the LW didn’t have that experience her first time. Lucky her!

  20. Fairhaired Child says:

    I agree with everyone who posted above, there really isn’t a right or wrong answer. However, if you suddenly tell him late into the relationship then it may be very startling. Some other responses touched on the fact that since he was a close guy friend before a boyfriend then he probably already knew that you weren’t that experienced with guys, and that could mean that you were a virgin. If it would have been inmportant to him (knowing that you were possibly inexperienced) then I believe that some guys would ask before sex about “how far you’ve gone”.

    It’s really up to you LW on if it really nags at you that much, or if you are content not telling him unless it comes up in conversation somewhere later (maybe a bunch of friends hanging out gabbing about “first times”) and then you can just casually state it.

    Good luck on figuring it out on what you want to do, and so far he seems like a nice catch since you guys were close first, and you seemed to have a good experience from sex so far. 🙂

  21. Been there done that... says:

    So, I’ve been in your shoes…the only difference I was 22 and I hadn’t really known him before we started dating.

    I didn’t tell him or at least I waited almost 2 years before I told him (he’s my current boyfriend). I never lied to him, but I just never really bothered to lay it all out. Now, that said, its not like there weren’t signs that this was my first time, although sweet (and slightly spacey) boy that he is, he never picked up on any of them. I wasn’t ever really going to bother to tell him, until he flat out asked me if he was my first and since lie wasn’t an option, I told him.

    Now, he was first shocked and he wasn’t happy about it, his reasoning being that he loves me and he loves that I’m with him and he’s sorry that I never got to “try” it out with anyone else.

    However, he also mentioned that he’s glad that I waited so long to come out with it. He says that he would’ve worried that I would’ve stayed with him only because he was my first (which is not true, and in this case I stayed with him because I love him and we’re good together). However, he says that would’ve been something that he would’ve worried about.

    I don’t know whether this is helpful at all (I’m pretty tired so my writing must be awful), but as someone who has gone almost the exact same experience, here’s my take.

    1. sarolabelle says:

      he’s sorry you never got to “try” it out with someone else? That seems a little wrong of him to say.

      1. Actually, that is a very common response, particularly with guys. They are generally taught to believe that sex is about the number of partners you’ve had, not the quality of partners or how much you care about them. I think what he was really saying is that he didn’t want her to regret that she had only ever been with one person. It’s a valid concern, and if LW tells her boyfriend, she should probably be prepared to answer that question.

  22. Like the others said, it’s up to you. I was 22 when I lost my virginity, and I told the guy before we had sex because I wanted him to understand if I didn’t quite know what I was doing or if I was awkward. If you’d feel better getting it off your chest or want to share the information with him because you’re close, then go for it. If it doesn’t matter to you either way, then you could just wait until it comes up in conversation.

  23. SpyGlassez says:

    I am 30, and I’m still a virgin; I have been with my BF for 18 months. I told him just before we started dating, because he was my first everything (first kiss, first “I love you,” etc.). I had dated in high school, but only one guy, and only the kind of in school, holding hands, etc. relationship people have in high school. So to me it was important to know if this was an issue beforehand. Since he knew this going into it, he has been ok with waiting till I feel ready.

    For you, it is up to you whether you want to talk about it or not; I would tell him if it is important to YOU, but remember that it might not matter to him at this date. Then again, it might.

    1. sarolabelle says:

      Add me to the 30 year old virgin club with you! 🙂

  24. How the effballs could he not tell that you were a virgin? Does he only have sex with virgins? Because losing your virginity sex and regular sex (as you know) are two comPLETEly different things. I would say, if you think you could be in this relationship for a long time, tell him, because the gap in his knowledge about a big event in your life that he was a part of will take its toll in your headspace. If its more of a short term thing, relax. But man, he didn’t know?? Maybe he thinks hymens grow back like lizard tails.

    1. You do realize that not every woman has a hymen when she loses her virginity. Mine was already broke by that time. Horseback riding, tampons, thin or non-existent hymens and many many factors can make it break early and without sex.

      Mine would have never know. It did not hurt, I was not scared, I was ready to go. That first night we did it 5 times. So virginity sex for me was no different than all the rest of the sex that I have ever had.

      1. I guess… I mean, damn, congrats for that. I guess I’ve heard way more stories of girls being at the very least very uncomfortable the first time rather than pleasured. Even if my hymen was broken I still think I would’ve maintained the HOLYSH*TTHISISNEW look on my face. But hell, good to know there’s better versions out there.

    2. SpyGlassez says:

      Also, when I went on birth control for my cramps and irregular bleeding, I had to have a pelvic exam and pap smear, and I am positive after that incident that I no longer had a hymen.

  25. I think deep connections start with gut wrenching honesty, say the absolute truth without fear of repercussions because it is the truth. If it is worrying you, tell him. If it is a private matter, keep it to yourself. I think the most important thing is not to be ashamed that you lost your virginity later in life, but that you waited for the time that was right for you.

  26. I recently started dating someone and after one month I decided to become intimate with him. I am 27 and he is 31. I knew that he was quite experienced and that he was actually married when he was younger. I on the other hand have very little dating experience and was a virgin. I didn’t want him to know about my virginity and planned on not saying anything. Of course the topic came up because he recognized how nervous I was when we started to get hot and heavy one night. I wound up lying and said I slept with one guy when I was 19 and it didn’t last long. He started asking more questions and I told him I didn’t want to discuss at that moment and he stopped asking questions. We wound up sleeping together for the first time that night and he believed my “story”. I felt so guilty about lying and wanted to tell him so bad. I finally told him about 2 months later. He was saying how he was so glad that I hadn’t been with many guys and that many women from his past obviously shrunk their number. I told him that I actually inflated mine. At first he didn’t believe me but then realized I was serious. I apologized for not telling the truth and explained why I lied. He was very understanding and told me he was so honored to be my first. I feel so much better about getting the truth out to him!

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