How Do I Tell My Girlfriend I’m NOT A Virgin?

Estimated reading time: 16 minutes

Dear Dr. NerdLove, 

I’ve been trying to find an answer to my situation and I don’t think I’ve seen anyone answer a question like mine before, so I hope you can help me. I have a problem that isn’t like most people’s. I need to tell my girlfriend that I’m not actually a virgin like she thinks I am.

I guess I should explain. I (20, M) have been dating my girlfriend “Samantha” (20, F) for about three months now. When we met, I’d told her that I hadn’t had a real relationship before and she was excited to be my first. In fact, she’s been incredibly excited to be my first for everything, including my first time. 

Samantha’s been incredibly loving and supportive and doesn’t think that my having never dated before is a bad thing, which I really appreciate. I was afraid that she was going to see my having never had a girlfriend as some sort of red flag. But that’s what makes things awkward. You see, she’s looking forward to my losing my virginity to her, but I’m not actually a virgin.

I was never one of the cool kids in high-school but I had friends who were friends with them, so when they would get invited to parties, I’d get to go along. The summer of my junior year, I went to a party at someone’s house and got drunk for the first time. Apparently I ended up dancing with a girl I knew, then we were making out on the dance floor and then later on she and I hooked up. I honestly don’t remember much about things, just a lot of unclear memories and waking up with both of us trying to get back into our clothes and trying not to be sick at the same time. The only thing we know for sure is that there was a used condom in the trash. She and I never really talked about it after, but she was always friendly to me afterwards so I guess we had a good time?

Anyway, I haven’t brought this up to Samantha and I don’t really know how to say “hey, I know we talked about your being my first but I’m not really a virgin”. I’m worried that she’s going to be hurt that I lied and I’m going to get dumped because I wasn’t honest with her. My friends tell me I shouldn’t say anything and that my first time didn’t really count since I was drunk. My conscience tells me I should tell her everything. I don’t know what I should do.

Please help?

Feels Like The First Time

Alright before we get to your answer, FLTFT, I’m going to be honest: your question sounds like the plot to a book I read a few years ago, so I’m going to reiterate the DNL policy on potentially fake letters: if the question may be helpful to other folks in similar situations, I don’t worry about whether a letter is 100% authentic. Every letter is ultimately hypothetical to everyone who reads it – besides the original writer, anyway – so the idea that someone’s trying to sneak one by me doesn’t bother me that much.

And to be blunt, I don’t run the ones that’re obviously in bad faith or obviously trying to pull a fast one on me to shit on someone else.

Since your question deals with some topics, especially regarding virginity, what “counts” as losing your virginity and honesty in relationships, we’re just gonna roll with it. 

So with all that in mind, FLTFT… this is an interesting one. I get a fairly sizable number of questions about whether people – usually, but not exclusively men – should conceal the fact that they’re a virgin from potential partners. Most of the time, if I’ve gotten questions about people who want to hide that they’re not a virgin, it’s usually from women who come from incredibly conservative religious or cultural backgrounds. So a guy hiding his having had sex is, admittedly, a novel one here at NerdLove Industries.

However, this is one of those times when I think you actually have two questions running in parallel. The first question would be “is it ethical or permissible to lie about being a virgin (or not)”. The second would be “what counts as losing your virginity?” 

I want to tackle that second question first, in no small part because, frankly, I think it’s the more important one. For all that people make a fuss about the significance of (or problem with) being a virgin, virginity isn’t really a thing. It’s a social construct, not an actual state of being, and there really isn’t any meaningful definition that isn’t full of more holes than a ten pound block of Swiss cheese. What, precisely, defines virginity and how do you define losing it? If it’s strictly about penetration, then that opens up a lot of questions. Do gold-star lesbians count as virgins since they’d never had sex with men? Do gay men who only do oral sex or don’t have anal sex count as virgins or non-virgins? What about a gay man who’s strictly a bottom? Does it count if it’s anal penetration and if that’s the case, does that mean that the Christian kids who tried to exploit God’s Little Loophole aren’t virgins?

If someone penetrates their partner with a strap-on, does that count as losing one’s virginity, and if so, who’s the one losing it, the person doing the penetrating or the receiving? And for that matter, if a sex toy like a dildo or vibrator would count in that instance, does that mean that someone could theoretically lose their virginity to themselves? 

Similarly, if we accept PIV penetration as the defining standard for virginity, then what precisely counts? If someone doesn’t fully penetrate – they go soft, they play “just the tip” – does that count? How many thrusts are needed for it to technically be sex? Do the Mormons who practice “soaking” (don’t Google that at work) count? What if they have someone jumping on the bed for them?  For that matter, what about if penetration may or may not have happened? Does it really count – or count for less – if someone loses their virginity to a sex worker? If a guy loses his virginity in the woods and nobody’s there to witness it, does it really count? 

If you ask me – and, well, you did – I’d say that intent matters far more than the actual act. Oral sex is sex; it’s right there in the name. So is anal sex. So are other forms of getting people off. I think if you and your partner decide to interact with each other’s genitals for the purpose of intimacy and/or orgasm, I think its fair to define that as “sex” for one’s purposes, in no small part because it doesn’t fucking matter except to the people doing the deed. A person who’s got a hymen isn’t meaningfully different from someone who doesn’t and a person who’s put their junk in someone else’s – or had someone else in theirs – isn’t magically different from someone who’s never had anything of the sort. It’s just an experience that someone has or hasn’t had yet, no more or less significant or important than someone who’s been downhill skiing or bungee jumping.

Not having been skiing only means as much as any one person decides it does. Same with having sex. 

In your case, FLTFT, you had a sexual experience of some sort. You and your partner were apparently hammered, so there’s an open question as to what happened. You might’ve had sex, you might have orgasmed as soon as the condom was on, you and your partner may have used a condom for oral sex… there are enough unknowns here that this almost serves as Schrodinger’s First Time. In the absence of evidence otherwise – and really, I’d say this even if there were video proof of the two of you going at it like Jorge El Niño and an obliging MILF – I think you’re in a position to decide for yourself whether this “counts” or not. So if you want to either say it doesn’t “count” or assume that you didn’t complete the deed, you’re well within your rights to do so. Or you can decide that it did “count” and you are now in the Fraternal Order of Sex Havers. Up to you, really.

The question of “is it ethical to not tell your girlfriend” is… well, that’s where it gets thornier, mostly because now it involves someone else’s informed consent to a degree. A lot depends on how your girlfriend feels about this. Most of the time, the guys who are worried about lying about their status as virgins are worried that their partners are going to see that as a red flag – mostly under the assumption that their partners would assume this means there’s something wrong with them or that they’re just going to be shit in bed. Your circumstances are a bit different, and a lot depends on your girlfriend’s feelings on the subject.

Would she, for example, not have started dating you if she knew that you weren’t one of the Great Untouched? Is her interest in sleeping with you contingent on your status as a virgin? If she would have decided otherwise, then yeah, it’s not cool to lie about it. But what if it’s not a lie? What if you decided that no, that experience didn’t count? Well… on the one hand, I could see an argument for saying that you’re telling the truth and that this isn’t a lie, at least to you. But on the other, if she has strong feelings about what virginity means, then “it’s true… from a certain point of view” has never really mollified anyone.

(Ask some OG Star Wars fans about how that worked out.) 

At the same time, however, I think that how you genuinely feel about it – and I emphasize “genuinely”, not just claiming it so that you can bang someone – matters more. If someone’s going to lose their shit because they think X counts and you don’t, then that’s more of a “them” problem and a matter of compatibility than ethics. Think of it this way: if a guy will refuse to sleep with another person because that person doesn’t have an intact hymen, that’s the guy’s issue. Hymens aren’t signs of virginity and the lack of one doesn’t mean that someone’s had sex. 

Now with all that having been said: I’d err on the side of honesty with your girlfriend. Not because I think your not telling her would be bad – especially since the odds of her ever finding out are low – but because you seem to want an emotionally intimate and lasting relationship with her. Sharing this aspect of your history with her in all it’s confusion and complicated feelings is a sign of trust and vulnerability – things that help make a strong and successful relationship. It’s not as much about informed consent so much as “this is part of who I am and what makes me me”, information that she would likely appreciate. I don’t think that this knowledge would influence her decision, but I think it would give her a more complete and rounded picture of you as a person and influence how the two of you go about having sex for the first time. 

My advice is to have an Awkward Conversation about this. Explain that you haven’t told her about this because you feel conflicted and a bit embarrassed about it, how you have some complex feelings about whether that encounter “counts” or not and how what you ultimately want is for your “real” first time to be one that you deliberately chose, with someone who’s important to you, not an event that you can barely remember and one that you aren’t even entirely sure what you did. I would emphasize that you still think of yourself as being a virgin, even if this would slide under a technicality and that you see the intimacy and connection with her as being more significant and important to you than a random hook up. The odds are good that she’ll understand and that she’ll appreciate your being open and vulnerable with her about this. 

And for the record, I think you can claim having sex with her as being you official first time. The fact that it’s likely going to be much more significant and meaningful to the two of you is more important than any technicalities from a night you can barely remember. 

Good luck.

Hi Doc, I am a 27 year old male, I am writing this because I feel my particular issue has not been discussed and that is having Christian parents while living at home trying to date.

For some context, after high school I began community college, but stopped after the first year to try electrical work. My parents decided to move from the area I went to high school so I moved as well since I did not make enough move out yet and then decided to go back to community college and finished my associates degree in IT.

Still living with my parents at this point, I have gone between several IT support jobs but still don’t make enough to afford to move out without getting a roommate.

I feel my situation is different then what’s been addressed because my parents are Christian and don’t believe in letting me have girls sleep over before were married. My parents do not even want me closing the door to the room I’m in if I have a girl over. They will not give me a hard time if I sleep over at a girls house they simply state that those are the rules under their roof.

I have felt reluctant to even try to date for many years because it will look like my parents are treating us like were 15. I have brought this up with them, they are not forceful about it they simply state that’s what they believe in and it will not change, and I have been respectful of that.

I have not been on a date since I was 21 and I had not even tried to find someone until about a year ago due to still living at home. I don’t like dating sites so I have been going old school going to bars trying to meet someone. This has not been successful so far and I have been considering trying dating sites but I have been to worried about being 27 and having to tell girls I live with my parents and it being compounded by the fact that they cant stay over or even been in a room with the door shut with me.

I am not looking for hook ups either, which has made me feel like girls my age who also want a serious relationship would not want to deal with my situation.

Sorry for the long winded comment, I hope you can provide some advice on how I should approach this situation.

Thanks

No Place To Go

I think the fact that you live with your parents isn’t as much of an issue for dating as you might assume, NPTG. As I’ve said many times before, a majority of Millennials and Gen-Z live in multi-generational households; it’s hardly unusual and the self-imposed stigma about it is out of proportion to the people who are in that situation.

The bigger issue here is that your parents seem to have not accepted that you’re a grown-ass adult. That, to my mind, is the bigger problem here. But that’s a them problem, not a you problem, in as much as that their attitude towards you reflects on them. You don’t need your parents’ sign-off to be a grown-ass man. The fact that they treat you like a tween is much more shameful to them than it is to you; it suggests that they’re living in a cloud of denial and refuse to believe that you’re an autonomous and independent individual. That shames them.

The first question I usually have for people dealing with issues surrounding parental disapproval or attitudes towards their love life is “are you materially dependent on them?” In this case, yeah, you are, which means that they actually do have the leverage with which to say “my house, my rules”. The rules in question, again, are pretty fucking absurd to be imposing on a grown-ass man, but they do have the authority to issue them and to enforce them.

This is why the first thing I would suggest is to start saving up as much as you can in order to move out as soon as is feasible. It would go a lot faster if you found a place and moved in with a friend – or at least someone you can get along with well enough to share living space. I’m not entirely sure why you would hesitate to get a roommate; it’s pretty widely acknowledged that there’s an absolute crisis in affordable housing, so splitting the rent with someone isn’t exactly going to be a mark of shame, no matter how old you are. But if that’s not an option for you right now, it’s not an option, so let’s talk about alternative possibilities.

The fact that you may not be able to sleep with a hypothetical date at your place doesn’t mean you can’t date. Your parents may have a “no women past 8 PM” rule like a boarding house from the 20s, but that doesn’t mean you don’t have options. The most obvious option is “sleep at her place”; your parents have made it clear that this is permissible for them. It smacks me as being stupidly hypocritical – if it’s sinful to do it at your place, it’s sinful everywhere – but whatever. People will twist themselves into knots over the dumbest shit.

The other option is “get a hotel room” or rent an AirB&B. As they said: it’s their house, their rules, so get your kicks outside of their house. There’re even apps like HotelTonight that help you find rooms at the last minute, usually at a discount. Renting a room somewhere would even give you the option of long weekends together, so you don’t feel like you’re having to sneak around at some No-Tell Motel like a Republican politician cheating on his wife. 

But the bigger issue here – for you, anyway – is how you let this affect you. You and your parents are having a conflict over boundaries. They’ve made it clear: this is a hard limit for them. You can either accept that this is a limit for you, too, or you can establish your own boundaries – including “I’m not going to be treated like a child”. The core part of enforcing boundaries, however, ultimately comes down to what’s actually in your control. If you break their rules, they have the authority – both literally and effectively – to kick you out. If they violate your boundary – not treating you like an adult – then that should be contingent on your presence in their life. If they want you around, they can acknowledge that you’re 27 goddamn years old. If they’re going to act like you’re a kid, you can and should take off – especially since their issue here is apparently “sinning” is ok as long as they don’t get splashback from God over it. So I would make it clear: this isn’t cool, you’re not going to tolerate it and minimize your time with them as much as is possible until you can actually pack you shit and get out. 

I would also suggest that you take that attitude of “this is only temporary and I’m getting my own place as soon as possible,” and hold onto it as you date. Reminding yourself that this is a temporary situation that you’ve been forced into by circumstance is important. Everyone understands the realities of life, especially with the economy the way it currently is. If you see your living situation as shameful, then that’s going to hinder you in dating – not because of what other people think, but because you are letting it hold you back from even making the attempt. Reminding yourself that this is temporary, imposed from the economic realities of life in 21st century America and not something you’re “stuck” with will be important. 

It’s worth remembering: anyone who you would actually want to date is going to be dating the holistic “you” – everything about you, not just where you live or who you live with. That means that someone worth dating will be understanding, even sympathetic with your circumstances. The people who are going to have serious issues with your living with your parents – outside of their absurd restrictions – are people who will assume that this is a “failure to launch” situation, not “it’s next to impossible to get a place to live on the average salary”.

If they think that, then clearly they don’t know you, don’t care to know or understand your situation and have thus proven that they’re not right for you in the first place. 

Good luck.