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

DEAR FEELS LIKE THE FIRST TIME: Alright before we get to your answer, FLTFT, I’m going to be honest: your question sounds an awful lot 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 it’s fair to define that as “sex” for one’s purposes, in no small part because it doesn’t f--king 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.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I’m a longtime reader, and have even tried putting some of your advice into practice, but likely haven’t put as much effort as I should have. My question is: how do I get started?

This is a little more complicated than it sounds. I’m a virgin at 39, on the spectrum, and currently living with my parents for the next few months (it was only meant to be a few months, but turned into years as my parents suffers health problems and major money problems). I also suffer from depression and severe social anxiety. So there are my main excuses – bad at socializing, bad with my emotions kicking my ass, and broke and living with mom and dad when I’m about to become middle aged.

As for my past, I have never dated, ever. I’ve had a few chances, but I literally cannot tell when someone is flirting, and have been told by a witness that sometimes a girl has actually tried flirting with me. I was too scared to even talk with girls in high school, any of my colleges, and only tried once at a job that led to very embarrassing results. I can’t even keep a friendship going, as most people find me boring after a while, but I also am in an area where finding people with likeminded hobbies and interests is rare (let’s just say I live in a place in Florida where even churches have political banners out front). So I just don’t have any history in sex and romance, and the few times people have either assumed this or I’ve hinted at it have led to some rather disparaging remarks.

Now here is what I’ve done in the last two years that counts as progress: I’ve taken an accelerated college course for a business degree, and despite a severe bout with depression nearly derailing that for a fourth time, I am only a few classes from graduating, likely in March. I am planning on following that up with getting a computer tech certificate with Coursera, and am taking a TEFL course in Mexico to teach English while I live in Mexico. I have started taking my hobby seriously (indie game dev, not aiming to be one the big success stories but make a steady living), and have started working out (for maybe the 10th attempt). I can’t promise all of these will prove fruitful, but I am trying.

So I’m asking how to get started in dating. On my good days, I don’t think I’m hideous, just very average and kind of forgettable looking. I have a stutter, but I’m not embarrassed by it normally, just a little frustrated at times. I am also an introvert, and know what places I just can’t get comfortable at tend to be the most popular for meeting people (bars, clubs, and concerts, or anywhere that’s crowded and loud just send me into a panic). I know my situation is a little less common (I am moving to Mexico, not just visiting, as I refuse to give up this time), but do you have any advice on how someone like me (older virgin with no experience) actually try dating or meeting people?

Thank you for any advice you can give.

Getting a Late Start

DEAR GETTING A LATE START: This is an increasingly common question, GLS, and I want to start with the same advice that I give a lot of people in your position: stop talking yourself down. You put far more effort into telling me why you can’t date or why you think you’re disqualified from dating and not nearly as much effort into acknowledging your good points.

You’re autistic and can’t tell when folks are into you? OK… that’s a challenge, not a disqualification. Yeah, it can make some social situations more difficult than they would be if you were neurotypical, but autistic people can and do date, have relationships, get married, have kids, the whole nine yards. The same goes for introverts – they have to plan how to manage their social energy more than extroverts do, but that’s just a difference, not a disqualifier. You live with your parents? Well, so do half of Millennials… I’m sure you see where this is going.

Now how about instead we talk about some of your good points – the ones you’re underselling. You’re generous and family oriented – you live with your parents because they have health and financial struggles! That’s goddamn admirable. You suffer from depression, but you’ve pushed through to get your degree – despite having failed before. That means you’ve got grit and determination and no small amount of ambition! You suffer from social anxiety, but you’re about to move to another damn country! That tells me you’re brave. You’re ambitious, you’re focused… these are all great goddamn qualities to have, things that people look for in a partner.

The things you worry about – being a bit boring, having a hard time connecting with people, being slightly awkward or afraid to talk to women… these are all things that can be fixed with practice and effort. The same with “just being a little forgettable-looking” – that’s a matter of working on your style and presentation.

In short: you’ve got a lot more going for you than you give yourself credit for. You have some challenges, sure, but most of what you think are handicaps are just matters of practice and experience. That’s all.

Now I think part of the problem you’re facing is that you’re focused more on an end-goal that seems nigh-impossible… or at least it does for now. I think what may help you more is if you decouple what you’re trying to do – improve your social skills, get more comfortable with meeting and connecting with people – and the ultimate end goal of getting a relationship. I think the seeming immensity of that goal is intimidating you, where if you just get rid of that last part – the “and get a relationship”, you might do better.

Let’s try looking at it in terms of coding and game development. When you first started learning how to code and develop games, you understood that it wasn’t just a case of “ok sit down, hit some keys for a bit and boom you have a game”. You had to learn a number of different, but interrelated disciplines. You had to learn to code, you had to understand graphics, design, rigging and animation. You had to have the math right to get the various systems to interact properly. Narrative flow and storytelling were important for making sure the game connects with its audience. Getting a solid base in these skills meant that when you sat down to work with a new engine – or trying to get an older engine to do things that it wasn’t designed for – you had a solid foundation to work from. Yeah, you may be using Unity or Unreal Engine for the first time… but you know its mostly a matter of getting used to that engine’s particular quirks. You had the skills necessary to make it happen.

Well, the same thing applies to meeting people and building relationships with them. It’s a series of seemingly disparate but intertwined skillsets that all merge together to give you the basic foundation of human interaction. So, since we know some of the areas that you feel deficient or less skilled in, we have a good place for you to start.

Let’s talk about your social anxiety, to start with. There’re two ways to approach this. The first is top manage the symptoms. Mindfulness meditation, self-directed Cognitive Behavioral Therapy exercises and managing your breathing all can help turn the volume down on your anxiety – they won’t eliminate it, but it can definitely serve to say “shhhhhhh” to your brain. And If this is a serious hinderance to your life, there are medications that can help – talk to a therapist or a counselor about what might work for you.

The second way to approach it – one I suggest that you apply in conjunction with the first – is that you treat meeting people as practice. Rather than worrying about trying to talk to women that you’d like to date, look at it as “I’m learning how to be more social”. If it doesn’t work out perfectly… well, it may be a bit awkward, but hey that’s the point of practice. You’re supposed to make mistakes and learn from them. Learning from your mistakes teaches you the most important lesson: that mistakes aren’t fatal, that failure isn’t permanent and you can recover from a truly surprising number of errors.

What about just meeting people in general, especially if you can’t do the bar or club scene? Well good news! The people you’re most likely to be compatible with aren’t likely to be there either, so going to bars or clubs or large crowded parties would just be a waste of your time. Fortunately, we meet people in all sorts of places. And since you’re planning on moving to Mexico, you’re actually in a position where you are more likely to find opportunities to meet folks.

The best way to go about doing this is to lay the groundwork in advance. Start by looking for online communities in the general area that you’re planning to live – Facebook groups or subreddits for expats and recent immigrants, community groups for people who already live there, etc. – and start participating there. Get to know some people virtually as part of your preparation for the move. The odds are good that you’ll make some contacts before you even get started packing everything into boxes, giving you at least a few people to say ‘hey’ to and help get you situated in your new home. Once you’re moved in or at least well on your way, you can even start asking if anyone has recommendations for places to hang out, cool restaurants or bakeries or the like to try, book stores or gaming centers… connect with people on that level and by the time you’re moved in, you may well have people who will be happy to show you around and help you get comfortable.

Those may not be your best friends for life, but at the very least they’re a good starting point; they can point you in the general direction of places to hang out and meet people that will be much more your speed than loud and chaotic venues.

From there, I recommend the classic move of “find a place you like and become a regular”. Becoming a known quantity – whether at the diner, the library, the coffeeshop or what-have-you – makes it easier to forge connections with the other regulars, if you’re willing to show some curiosity and interest in other people. This – incidentally – is also a good opportunity for you to practice your social skills.

I’d also recommend finding the communities there that match your interests. I’ve no doubt that there’re going to be other indie devs around you. Finding the places where your fellow game developers hang out, participating in game jams and the like will all be good ways of finding your people.

What about your difficulties in, say, telling when people are flirting with you? Well, first and foremost, you’re hardly alone in this; people are bad at telling when others are flirting with them in general. But in your case, I’d suggest leaning into the fact that you’re autistic. Right now, you seem to see being autistic as a negative, something that’s a hinderance to people liking you. But what if, instead, you just treated it as neutral, a simple fact about you? Being up front about things, rather than masking – telling folks when you don’t understand, asking questions if you’re unsure what they mean, even just saying “hey look, I’m autistic, so I’m going to miss stuff and it works better if you just tell me straight up” – then it goes from being something you have to hide or adapt to and just “this is part of what makes GLS who he is”. And as someone who’s speaking Spanish as his second language, asking for greater clarity and directness is going to be pretty understandable.

Yeah, I know, this all seems like a lot. But by breaking things down into discrete skillsets that all work together, it’s much easier to focus on the immediate need – working on your social skills – than putting all your effort on the overall goal of Finally Start Dating.

But funny thing? If you do start putting these into practice and working on them individually, without trying to date or meet people? You’re going to find that people will start coming into your life organically, almost without conscious effort on your part. All you’ll be doing is just living your life. Spending time in local hangouts and getting to know the other regulars will make it that much easier to find folks who grab lunch with or go see a movie. And if you make a point of making friends across the gender spectrum – talking to everyone, not just people you’re attracted to – then you increase the likelihood of meeting the people you’ll be compatible with. Some of those will likely be interested in dating. Of those who aren’t… well, they may not want to date, but if they’re your friend, they may well be the person who introduces you to the folks who do want to date you.

So TL;DR don’t worry about the destination and put more of your attention on the journey. Working on those aspects for their own sake will be what put you in the position to meet awesome people of all sorts. Some will be valuable networking contacts, some will be good friends… and some could well be your first step towards love.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com

DEAR DR. NERDLOVE: I saw this handsome guy who had braided his hair around Takoradi market circle seated in front of a shop with another guy who had also weaved his hair. we gazed at each other a lot. He start to follow me around but he couldn’t talk to me neither did I cos I was with my dad and bro now I regret not approaching him and I don’t know where he is now and I can’t stop thinking about him.

What do I do now Dr?

Want A Second Opportunity

DEAR WANT A SECOND OPPORTUNITY: This is going to sound like an odd digression WASO, especially if you didn’t live in America in a very specific point and time, but stick with me for a moment.

You know what I kinda miss? I miss the “Missed Connections” section of personals. Whether it was the classic alt-weekly page-filler or the best part of Craigslist, Missed Connections were just a gold mine. For every “you blinked twice at me while also being unspeakably hot, clearly we’re soulmates” entry, you would have dozens of flash-fiction stories, little moments of human connection in 200 words or fewer. So many little points of time when you can practically see the branching arcs of their stories, little hits of possibility that range from brief conversations to living lifetimes in the span of one evening, Before Sunrise-style.

And so many of these stories hinge on the tension between a burgeoning attraction and the fear that these moments are more ephemeral than a soap bubble and more easily lost than tears in the rain.

And most of the time a reminder that you miss 100% of the shots you don’t take.

(The rest of the time, they’re a reminder that computers and phones will go dead at the most inconvenient times, so keeping pen and paper on hand will never go out of style.)

But while the romantic in me likes those stories and I can turn off the dating-coach part of my brain long enough to appreciate them as stories, they’re still often a case of someone making a mountain out of a molehill and mistaking physical attraction for… well, something far less fleeting.

Now I mention this precisely because that’s what we have here, WASO. For all that it feels like the opening lyrics to an old standard – some enchanted afternoon, you’ll see a stranger… – this is just a moment. You saw a really pretty man and had a moment where your stomach did flip-flops. That’s ultimately all it was. Everything after that is your brain filling in a whole lot of blank spaces and “what ifs” based on nothing more than “really handsome guy at the market looked at me”. It’s very easy to regret those because now that missed connection is literally anything you could want it to be. He could be a gangster with a heart of gold who needs the love of a special woman to show him a different way of life. He could be a tech entrepreneur visiting his old haunts with a friend from back in the day, whose life of wealth and influence is lacking someone to show him what’s important in life. Or he could be the impulsive, devil-may-care kind of person who lives every moment of his life to the fullest and wants to show you the beauty and adventure of the world around you.

None of this is to say that he might not have been an awesome guy, don’t get me wrong. It’s just worth remembering that you don’t know anything about him other than his looks and that you missed your chance to learn more. Everything after that is just an exercise of your imagination, letting him become whatever he represents to you.

So what do you do now? Well… you can always revisit the market and hope that fate’s willing to smile on you twice. There’s a non-zero chance that you could run into him again if he and his friend hang out there regularly. But if I’m being honest… this is a long shot, and the odds that you’ll run into him are very, very low.

What I’d suggest is that you take a lesson from this: fate (or God, the Force, or the Universe) may show you a door, but you have to make the choice to walk through it. Luck is more than just random chance taken personally; luck is what happens when you’re in a position to make the most of an moment that presents itself to you. The people who we see as being “lucky” tend to be the ones who don’t hesitate when they see an opportunity and try to take full advantage. If you see someone who gives you those butterflies and flip-flops, and your family isn’t going to prevent you, then swallow those nerves and go say “hello”. If you’re having a conversation with someone you’re into and its going well, be willing to take the initiative and ask for their number or to connect on WhatsApp instead of hoping that they’ll do it first.

Yeah, it can be scary and intimidating, but that’s the thing about leaps of faith: you’re taking a leap without knowing what’s going to happen next. You’re making yourself vulnerable in the moment, with someone you don’t know. That means you’re opening yourself up for the possibility of being rejected or the chance that they’re a case of Crouching Nice Guy, Hidden Douchebag. You run the risk of falling when you make that leap and you have no idea how far down the bottom may be.

And sometimes when you make those leaps, you fly.

But that can’t happen until you take that leap. So enjoy the stories of What Might Have Been with this handsome stranger in the market place. But let it be a reminder that you’re ultimately the one in charge of your own fate; mysterious forces may put you in the same place, but you’re the one who has to make it all happen.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com