When do I disclose which embarrassing/awkward sexual history fact?
September 11, 2013 9:15 AM   Subscribe

I'm an almost-30-year-old man who is very romantically and sexually inexperienced--basically virginal--thanks to insecurity (general) and insecurity (sexual identity-wise). Now I've found a great woman to date. But what do I tell her about my lack of experience (and the why of it). And when?

(I've seen a few of the existing "I'm a virgin do I disclose?" questions and a few of the "I'm a bisexual do I disclose?" questions. Here's a twofer. I'm interested to know how people think the combination changes things. And in reassurance. That too.)

So in a previous, anonymous question I asked for advice on how to ask a woman out for a date after I had failed to follow through on a delightful--if chaste--weekend that we shared abroad. The answers were great. I asked her out over email, we've been corresponding and we'll be getting together for some sort of date when I'm back home. Wonderful. I'm excited.

I know the relationship may go nowhere: the spark we felt might fade, maybe she isn't as attracted to me as I am to her. But it might not! So there's the prospect of physical intimacy and that makes me nervous. I'm a huge dork, so in an effort to make up for my lack of experience in bed I've been doing my research--Sex for Dummies, She Comes First, various articles about first-time sex.

Now a common theme is that a couple should discuss their sexual history and get tested for STDs before they have sex for the first time. Sounds smart, but what do I say and when?

My sexual history is that I have dated only once, a woman I was with for a few months back in college. We fooled around but never got around to intercourse. The one night we gave that a shot we simply couldn't figure out the mechanics. Tab A into Slot B, yes, but there were all these limbs and pelvises and things in the way. After that: nothing. Not a sausage (or a, ah, bun?) for almost a decade. Not even a kiss.

Why? I will probably talk to a therapist about this, but basically just insecurity: general, social, and sexual. In addition to not liking my body and hating taking any risks at all ever, I spent a long time agonizing over my sexuality and never really came to terms with myself as someone who could really have a sex life or who can talk about this with friends. I guess "bisexual" is the term for me, but I spent a long time as a teenager thinking I was gay before starting to be attracted to women in college, and it took me ages to be at all comfortable with not fitting one sexuality or the other. And the label still doesn't feel right.

Sex with men has always been fun to fantasize about (maybe 75%+ of my fantasies?) but actually going out and making it happen seemed like too much to manage. I'm only out to handful of people in my life, because it always seemed a little pointless and a lot embarrassing when I'm not actually going out with any guys. (So much for solidarity, I know, and I do feel bad about this if it's any consolation.) In any case, with guys I've very rarely felt the kind of desire for physical AND emotional intimacy that I have for various individual women, including the one I'm involved with now. Added to that, for whatever reason my heterosexual libido ramped up considerably in the past year.

It's complicated. But regardless, I like this woman a lot, I'm hoping we continue to hit it off emotionally, and if we do I would like to proceed past Go, etc, to a physical relationship.

Not that I'll be rushing things. I know this shouldn't all come out on a first date or on the verge of our first kiss. But when do I bring it up? After we maneuver ourselves into the bedroom, something that I might not make a move towards for weeks? Over beers on a third (fifth, godforbidtenth?) date?

And do I just disclose the inexperience so she doesn't think I'm constitutionally bad at sex (and doesn't worry about STDs)? How? Do I go into why I haven't been seeing anybody? And if I do, do I gloss over the bisexuality? I imagine I should tell her eventually, but right off the bat seems like it would muddy the waters considerably.

Yes, I'm confident that I'm not really gay and in denial; no, I cannot see this bisexuality thing making me more likely to cheat (gay porn would continue be a temptation, though).
posted by sauberbrezel to Human Relations (24 answers total) 4 users marked this as a favorite

 
I see no reason to disclose, ethically. So, never, unless you feel like it.
posted by Ironmouth at 9:18 AM on September 11, 2013 [9 favorites]


Best answer: Probably easiest way to get at the basic safety question is to just get tested. That way you can say, "I had a test come back clean on such-and-such a date, and I haven't been with anybody since then."

You don't have to disclose your whole (not-sordid) past with this woman if you don't want to, though at some point down the road, you may find that you want to get it off your chest, in which case I'd bet that she thinks it is no big deal.

Don't make your inexperience into a great big thing. It's not. Go as slow as you need to. Do what's comfortable for you and for your partner.
posted by gauche at 9:23 AM on September 11, 2013 [3 favorites]


Best answer: Now a common theme is that a couple should discuss their sexual history and get tested for STDs before they have sex for the first time.

Ok, there's a slight bit of misunderstanding here. The foremost reason for discussing sexual history is to find out whether your partner has been up to anything dealbreakingly risky (e.g. "oh I was big into orgies.") A lack of sexual history, in this context, is practically irrelevant.

There are men (and women) of all ages, who have been having intercourse since they figured out how their genitals worked, and are awful at it. Seriously, ask anyone who has regular sex with different people how often the sex is actually good, and I guarantee the answer will be "infrequently."

Your inexperience is nothing you ought to bring up practically or should bring up ethically. The only way someone will think you're bad at sex is by being bad at sex. Pay attention to what your partner wants and finds hot and ask questions if you have to. That'll put you high above many, many other people in the "compatible lover" category.
posted by A god with hooves, a god with horns at 9:28 AM on September 11, 2013 [12 favorites]


Best answer: You may find the answers here interesting, being from the other side of this kind of thing.

My opinion is, disclose if you think it will help things go smoothly (like if the pressure of performing like you know what you're doing might pysch you out?). But, honestly, it only seemed to matter the first time or two in my experience. After that you're hopefully tuning in on what your partner likes, and whatever you may or may not have learned before is kind of irrelevant.
posted by cabingirl at 9:31 AM on September 11, 2013 [1 favorite]


Best answer: Can you make it more about finding out what she likes and/or wants physically from a relationship? I mean, y'all are obviously at the very very beginning of something here, but if, after you've had a couple of dates and are feeling comfortable with the hugging/hand-holding/kissing/general affectionate touching of your choice, could you not have a nice, relaxed heart-to-heart where you say, "So hey, what kind of stuff do you like? What do you absolutely not like?"

I'm sure there are some who would argue that it takes some of the spontaneity out of physical romance, but I had several of these convo's with my now husband before we got super intimate (and I was incredibly inexperienced before I met him), and I found them to be really informative and helpful. And some of them led into hot, fun times as well where we got to implement the stuff we had just discussed. I think that sort of a conversation could give you a nice chance to also say, "I'm pretty new at this," and then see how you two can work through that together. I don't think you need to give her a blow-by-blow of your history or even discuss how you've come to think about your sexuality -- if it can be more about how you want to build a personal connection with her where you're learning about each other, then I think you can keep it simple and honest.
posted by catch as catch can at 9:35 AM on September 11, 2013 [2 favorites]


I'm going to be the dickbag that disagrees with everything above and say: Yes, you should disclose that you are a virgin, and yes, it does matter. You've had so much insecurity and anxiety about yourself and your sexuality that you haven't managed to have sex in a decade. You still haven't figured it out, and you're not in therapy. This is not the standard type of history that one assumes when dating other adults in their thirties. This woman should know this information so she can decide if she wants to take this on.
posted by unannihilated at 9:37 AM on September 11, 2013 [4 favorites]


Best answer: 1. Get yourself tested for STD's, if only to be able to say "I've been tested, results were fine." in case it comes up.

2. You don't need to disclose anything. If, at some point, saying something like "I've got to admit, I might be a bit clumsy at this." would elicit some kindness on her side, go ahead and say that.

3. Your sexual preference, at this point, is still pretty ambiguous, leaning towards straight. I don't think you need to find that unusual at all, lots of folks are in those shoes!

4. Relax, focus on having fun and getting to know her better...the sex will follow as it should.

enjoy!
posted by HuronBob at 9:38 AM on September 11, 2013 [1 favorite]


Best answer: you should what you think it's comfortable. if it is nagging you, then bring it up maybe through email if that is easier. if she ifs the right person for you, then it won't be a big deal. remember that they are choosing to go on a date with you because they are attracted to you. being a virgin might even be a positive since it means you don't have STIs.

I am always a proponent of open conversation though. but you don't need to do it on the first date. focus on the present and if the topic of sex comes up, then you can bring up anything you think relevant. none of it needs to be revealed unless you want to and even then when it specifically is asked.
posted by Jaelma24 at 9:38 AM on September 11, 2013 [1 favorite]


Best answer: If I were your girlfriend in this scenario I would want to know about your inexperience. Not in an "OMG WTF is wrong with him!" way, but in a "Okay, I can take this a little more slowly and carefully to make this comfortable for him.". Plus, there is a lot to be said for being someone's first. People who have had lots of sex can be terrible lovers. The fact that you haven't had sex doesn't inherently make you a good lover, but you haven't learned any bad habits yet! This is a good thing. She may see it as a chance to "break you in" and get you making love in a way that suits her.
posted by PuppetMcSockerson at 9:41 AM on September 11, 2013 [7 favorites]


Best answer: I am (kind of) in a similar situation to yours. I am a woman and my serious relationships in the past have been with other women. However, I have noticed recently that I'm more attracted to guys and would really like to be in a sexual/romantic relationship with one.

Thing is, I've only have sex with one guy and saying it wasn't great would be an understatement. Although in my case, the opportunity has yet to arise with a new male romantic partner (much to my chagrin). However, I've thought about this whole lack of experience deal a lot, and the more I think about it, the more I've come to realize that it really falls back on your level of comfort/trust in your potential partner.

If you trust, like and feel comfortable around her (and the feeling is presumably mutual), the whole sex bit (at least in theory), shouldn't be too big of a deal. And I think part of that whole comfort/trust thing is also being able to tell your partner about your sexual history (or lack theoreof) and that that makes you anxious.

Also, in terms of sex, in all my inexperience, I'd have to say I think the most important thing is just really the intention of wanting to make your partner happy in bed. When I've had sexual partners in the past, the fact that they want to please me is far more important to me than whether or not I happen to orgasm (and vice versa, I hope?)

Also, as a queer women myself (who, I guess, is technically bisexual but doens't like that label)-- bisexual guys actually are a huge turn on for me, and who knows, maybe your date is one of those women, too. I actually really don't think it would/should be a big deal (I tend to be very open with everyone I date/might date about my sexual orientation)
posted by Ocellar at 9:43 AM on September 11, 2013 [2 favorites]


Best answer: Entertain each other with hands and mouths for the first few times, to relax and get comfortable giving each other pleasure in ways that are less likely to cause panic, awkwardness or performance anxiety. Tell her you're a little slow to get to know new people and a little inexperienced, and ask her to show you what she likes, in great detail.
posted by ead at 9:50 AM on September 11, 2013 [4 favorites]


Best answer: "I'm not terribly experienced" always seems sweet to me, rather than some kind of warning.

(Gay male here, so take it for what it's worth.)
posted by xingcat at 9:51 AM on September 11, 2013 [11 favorites]


Best answer: There are two issues here: one is your sexual inexperience, the other is your shame/embarrassment/awkwardness.

I'll discuss the awkwardness first. Your question was positively fizzing with excitement about what might happen with this woman which was awesome and great and gave me a lovely contact high, but you've got to stop being so self-deprecating. Lack of sexual experience isn't embarrassing or weird and there is absolutely nothing wrong with being late to the game. I'd also let go of this notion that you can be 'good' and 'bad' at sex. Sex is a matter of chemistry, two bodies colliding; what makes for good sex is honest, accepting, no-holds-barred lust shared between two people. What makes for bad sex is constantly holding back and fretting about what the other person might think of you. You need to get comfortable with yourself and your history. So you haven't really had sex yet. So what?

In terms of your sexual inexperience, I do think you should talk about this with the woman you're seeing. Keep it light. Pay attention to how she responds. If she's worth her salt she'll be glad you told her and see the sexual part of your relationship as a big new adventure. And so should you.
posted by nerdfish at 9:51 AM on September 11, 2013 [6 favorites]


Best answer: I was wondering how it went with you. I'm glad you followed through with our advice and asked her out!

First of all, as a woman, if I really like someone, I don't care how inexperienced they are. Chemistry can make up for lack of experience. (I am actually more concerned about how a less experienced guy would perceive me--would he think I was too "wild" or would it intimidate him?) If you feel you need to disclose, don't do it apologetically. It would be hugely flattering to hear that someone had been waiting until they felt comfortable, and I was the person they felt comfortable with.

And don't ever act insecure about your body or point out your flaws. Even if a woman is attracted to you, it is a huge turnoff when guys do that. No one is perfect nor should they expect others to be, and confidence is a turn-on.

As far as being bi, I don't think you have to tell her about that unless you feel strongly that it's still a part of your identity. I used to feel similarly regarding same-sex attraction. I experienced it to a degree, but my relationships and romantic feelings were all for men. I now identify as straight and I really don't see a reason to tell anyone that I once thought otherwise. It's not out of shame, it's just that it might confuse people. Unless you strongly identify as genderqueer and/or want to pursue same-sex relationships, I'd just leave that out.
posted by Rainflower at 9:59 AM on September 11, 2013 [2 favorites]


Best answer: Personally (I'm a straight female) I would appreciate a disclosure of your history and sexual orientation. It wouldn't have to be all at once. If you had had the chance to show me that I was important and special to you, none of it would be a big deal. I do have to say though, that a younger me would have found the bisexuality challenging. I would want to know rather than not know though. There are parts of my husband's past that he has chosen never to reveal to me and as good as our relationship is, those gaps still trouble me at times. I'm sure my imagination is far worse than whatever he's not telling, but at this point there's no way I'm ever going to be able to be totally relaxed about it, and that is a kernel of sadness in an otherwise fantastic relationship.
posted by WalkerWestridge at 10:03 AM on September 11, 2013 [1 favorite]


Best answer: Since it's not an issue of risky behavior, you don't have to tell her.

But.

This is you, this is who you are. It's embarrassing and awkward to you because of the baggage you've put on it, but to other people - for the most part - it's just the perspective you have. I don't think anybody's required to tell every single cringey detail, but telling someone that you don't have a whole lot of experience and you're learning as you go and you want to give and get feedback and going slow is not a terrible idea - those disclosures are good and helpful and promote intimacy. I think it's easier to bring all this up at a point where you've had some contact and it's starting to look like you are headed for pillows, but before any actual sex.

It's all in the presentation. It's okay to tell her you have some bad feelings about your lack of experience, but don't try to frontload her imaginary rejection by telling her how bad and shameful you are. You're not, and people don't want to be told how to feel. This is also not the most important thing about you, it's just a thing. It's just about at the level of having a bum knee that might prevent you from doing advanced sexual acrobatics - better to mention it so you don't strain yourself trying too hard.
posted by Lyn Never at 10:03 AM on September 11, 2013 [1 favorite]


Best answer: OK female here. I have had sex with different 2 guys (before I was married and not at the same time) that said they were virgins both were over 25, both had fooled around but never followed through to the "all the way" stage. Both were really good lovers, I've had much worse sex with guys that had no excuses. One was so desperate to try cunnilingus that I had the best oral of my life that first night. Basically enthusiasm and caring for the person can make up for lack of experience.

As xingcat says, "I'm not terribly experienced" is not a bad thing to say, and if you add something like "so let me know what you like" and I can't imagine any woman (or man) complaining. As for when to say it, I usually have the STD talk around the time kissing becomes a regular feature of the relationship, and I'd bring up the not so experienced thing around the time articles of clothing start coming off. Oh the tab A into slot B lining up thing happens to even experienced people the first time or 2 with a new person working out the angles is half the fun. If she has experience she will most likely help steer things in so don't be worried if things don't all just slide together magically like they do in porn and don't be afraid to use your hands to guide things in.

The sexual orientation thing I don't really see the need to bring it up unless it comes up naturally, maybe if you get to the watching porn together stage you can bring up that you like gay porn unless you are planning on seeing guys while dating her then I think it should come up around the time of the STD talk.

Good luck, I so feel like giving you a hug and telling you to go out there and have fun, this is the scariest part of the roller coaster ride that is relationships, just as it's cranking up the first hill, take a deep breath and don't forget to enjoy the ride.
posted by wwax at 10:23 AM on September 11, 2013 [6 favorites]


Best answer: It might not be the Best answer, but what I did (at an older age) was to maybe hint at being not very experienced. After getting the first time out of the way (like you, I was very anxious about it) I was able to talk about it more, and it was no big deal. Most people get better at sex with Each Other as they go along and get to know each other.
posted by ldthomps at 11:16 AM on September 11, 2013 [1 favorite]


Best answer: Now a common theme is that a couple should discuss their sexual history and get tested for STDs before they have sex for the first time.

While this is a common theme in internet discussions, it is not actually very common in real life, according to my own experience and the experience of other people I've talked to about it. That's not to say it's a bad idea, but don't just assume partners are expecting it of you.
posted by tylerkaraszewski at 12:35 PM on September 11, 2013 [5 favorites]


Best answer: I was in a similar situation re the experience (or lack of) aspect, and telling him was super-helpful. One of my dating issues had been that I was so shy and nervous about the physical thing (and psyching myself out about it because I felt like I ought to have done things I hadn't) that guys would interpret my carefulness as lack of interest when it was really just nerves. So when I finally met someone I really did want to pursue it with, I wanted to make sure he did not have any doubts about this. And it worked. Since he knew I was interested, he did not have to read anything into my behaviour other than what it was. That was two years ago and we are still together :-)
posted by JoannaC at 12:50 PM on September 11, 2013 [2 favorites]


Best answer: Disclosing your virginity will take a lot of trust, but if she's unable to deal with that, well, she's also going to have trouble with your many insecurities.

Here are some sites that may help:
http://www.scarleteen.com/
http://www.scarleteen.com/article/boyfriend/drivers_ed_for_the_sexual_superhighway_navigating_consent
http://www.scarleteen.com/article/body/with_pleasure_a_view_of_whole_sexual_anatomy_for_every_body
http://www.scarleteen.com/tags/virginityhttp://www.plannedparenthood.org/info-for-teens/sex-masturbation/what-sex-33828.htm
http://www.dummies.com/how-to/content/what-happens-during-intercourse.seriesId-225487.html
http://www.amazon.com/S-E-X-All-You-Need-To-Know-Progressive-Sexuality-Through/dp/1600940102
http://www.ugo.com/girls/sex-workout-guide-beginner - illustrates postions
http://ask.metafilter.com/tags/virginity
lots of attitude, but may be useful to read:
http://www.doctornerdlove.com/2011/10/sex-for-beginners/all/1/
http://www.nomoremrniceguy.com/forums/showthread.php?t=6091

The mechanics:
Take it slow, explore, caress, talk, ask what she likes, listen, tell her when she pleases you, really - take it slow. Make sure she's really ready - ask. Lubrication is really nice - go buy some. For beginners, the missionary position seems like a good choice. Face-to-face, with you and your legs between her legs. You've already explored her vagina with your fingers, right? and asked if she'd enjoy some extra lube and applied if she said yes, right? That helps you know where things are, too. Ask her to help guide you in. Take it easy.

FYI, an awful lot of people are terrified, anxious, awkward, etc. Some people have sex for the 1st time at 40, or 14, or never. It's okay to be a virgin, and it's especially okay to come to ask.me to get some help and support. I hope things go well for you both.
It took me a few boyfriends to get with the guy who was good at exploring, playing, learning, and I sure have fond memories of learning together. If you listen, are willing to try new things, want to please her, you'll be fine.
posted by theora55 at 6:22 PM on September 11, 2013 [3 favorites]


Best answer: I'm female, and most of my relationships have been with men.

Unless it feels somehow intrinsic to your identity or comes up in some other unsexualized and necessary way, I wouldn't mention being attracted to other guys. *Correction* I wouldn't mention being attracted to *anyone* else. Not your ex from college, not whatever guys you fantasize about, not any other women. Maybe this particular woman you've been flirting with is unshakably confident, but hearing your current partner fantasize about others is crazy-making for a lot of people (including me). And I think it's especially rough/harsh to tell your current partner that you've fantasized or been attracted to people who are utterly unlike her -- whether that means men as opposed to women, or people with a certain type of personality trait she doesn't have, or people who look totally different from her. When I've been dating someone and he's said a thing like that to me, it has made me feel insecure and I've had a really rough time shaking it. I've seen the same thing happen to guys I've been dating, when I've mentioned having experience with women or when I've brought up my exes in conversation -- so now I just stay as far away from doing that as possible. Unless you want a blow-by-blow of all the people she's found attractive, and how you don't have much or anything in common with them, don't give her a blow-by-blow of yours.

As for not having a lot of experience, she's probably going to figure that out really fast (but it's a pretty neutral thing, so don't worry too much about being "exposed" as a virgin). Good sex is more about having a good attitude and being responsive than it is about skill anyway, so don't worry too much about not having "practiced" enough -- and if there's anything she definitely wants you to do, just ask her to tell you about it. Personally, I've never had the STD talk, but I've had plenty of talks about what feels good! Totally normal, and can be very hot.

If I were you, I *would* tell her that I'd like to take things slow, because you do, and withholding that could result in some sad misunderstandings (ie, is he not coming onto me because he doesn't like me? is this a rejection? are we *ever* going to have sex? etc). I don't see why you'd spell it all out for her, though. If you want to tell her something general, like "I don't have a lot of experience," that's totally fine, and might make you feel more comfortable. But I don't think you need to go very in-depth with that -- again, because going too in-depth could make her feel pressure to reciprocate the candor, which could be uncomfortable for you and her both.

Maybe some of this feels strange to you because you're a guy and haven't been "trained" in how to deal with these situations, but honestly -- figuring out how to be discrete about your sexual past while communicating that you won't be terrible in bed, leaving behind an awkward/physically terrible virginity experience, and making sure the other person understands what pace you need to be on in terms of when you'll have sex -- this is all stuff that many women deal with constantly and which has been drilled into many of our heads. She might be a lot more understanding than you think.
posted by rue72 at 8:29 PM on September 11, 2013 [1 favorite]


Response by poster: Lots of great answers here. Not quite a consensus on what to disclose and when, but this is all helpful to me. Still not sure how I'll work this but I don't feel quite as at sea about it right now, and there's some great advice in here. Thanks!
posted by sauberbrezel at 9:05 AM on September 13, 2013


Response by poster: So in the end I hinted at my inexperience without having some sort of sitdown talk about it, although I did end up saying "I'm taking this slow, hope that's okay" in an email, more or less directly. Have left any question about my sexuality to another time when I imagine we'll both more comfortable about it.
posted by sauberbrezel at 12:12 AM on October 18, 2013


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