Hello, all you petrochemical sex cobras of the Internet. Welcome to Ask Dr. NerdLove, the column that puts the “Hell yes” in FPS.

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This week, we’re talking about experience. How much does being a virgin actually affect your dating success and how much of it is about expectations? And speaking of expectations: how do you handle your friends’ expectations when you’re newly out of the closet?

Let’s do this thing.

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Hi Dr. Nerdlove,

I feel like I should have reached out to you sooner, but I didn’t muster up the courage to reach out to you until now. I am currently a 26-year-old male who recently finished law school and took the bar exam. Now that I am moving on to working as a full-time attorney, I am starting to focus more on my future, which includes the search for a serious relationship with a woman, one that can hopefully lead to marriage if it works out. However, while I do not plan to focus on this until after I start working, I feel very uncertain as to how to deal with this situation. Simply put, I am a virgin who has no real relationship experience, and I take no pride in either of these facts. I guess I have never been interested in one-night-stands or just casual sex, preferring sex with someone I feel a genuine connection to. Still, I’ve never made a proactive effort to lose my virginity, so it doesn’t feel like I am in this situation by choice but rather my own shortcomings.

This lack of experience has made me feel concerned about my ability to find and maintain a successful relationship for a variety of reasons, the biggest one being that I feel like I don’t know what the hell I am doing and it just makes me pessimistic about whether I can achieve these goals.

Back in April of 2015, I decided to give some of the online dating apps a shot, and I ended up meeting about 15 women during the course of the 4-5 months I used these apps. However, only about 6-7 of them wanted to go on second dates, and I only went on a third date with one of them. I was so discouraged because I expected more success, though I realized over time how unrealistically high my expectations were and that I needed to really think about the qualities I was looking for in a partner. It also didn’t help that the one girl I went on three dates with tried to end things on the fourth date through indirect signals as opposed to just talking to me about it, which led me to wonder what I might have done wrong (she never actually told me what happened, we just parted ways and I realized it wasn’t worth continuing after realizing what had happened). Bottom line, I was grateful for these experiences, but annoyed by all the disappointment I had to put up with in the process.

I ultimately ceased using the apps once the summer ended to focus more on my last year of law school, but now that school is over I am thinking about how I want to resume these efforts. The obvious problem is that I have no idea what to do and am discouraged from doing anything because I don’t want to go through this much rejection all over again. Not helping matters is that I live with my brother, who has been going on dates and has had better luck on the first date alone, even though it has not yet led to anything serious for him. I admit I am not someone who aims for sex on the first date, but I also can’t help but feel a little jealous given my situation.

Since I’ve never really dated anyone exclusively before, I feel like whenever I try to date someone, I am uncertain and insecure about what to do, which may hinder my efforts. I know I want to find a serious relationship, but I am pessimistic about my chances of finding one. I just do not know how to approach this matter. I feel like the problem lies in both my lack of experience and my mindset toward the situation, because I know this bothers me way more than it should. What do you think I should do?

Confused and Looking for Love

Alright, CaLL, I think you have one big stumbling block here… and that’s your virginity. It’s not the problem… at least, not the way you think it is.

To you, your being a virgin is like a giant neon sign, a scarlet V blinking overhead. It’s an indicator of someone who’s managed to miss out on his window and now he’s screwed because who could possibly want somebody who’s still a virgin at his age? That big ol’ V is symbolic of everything you should already have figured out by now and the life that you think you should be having but aren’t.

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Thing is though: your virginity is pretty much irrelevant to most of this. The bullshit stigma that you’re feeling about your lack of experience—and the narrative of How To Be A Man that tells you you should be knee-deep in pussy right now—is throwing you off. You’re letting being a virgin psyche you out and it’s giving you a distorted view of what dating is like.

Let’s take your experience with dating apps as an example. Meeting 15 women in the span of four months is a pretty respectable ratio; that’s around a date a week. The fact that more than half wanted a second date is, again, pretty damn good; that’s a rate of more than 50%. You’re doing far better than you realize, with a success ratio that a lot of people would envy.

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Did you get a girlfriend out of it? No… but that doesn’t mean you weren’t doing well. Dating, and online dating in particular, is a game of numbers. You’re going to have a lot of false-positives - people who seem appealing on paper at first, but that you don’t click with once you spend time with them. You’re going to have dates that go nowhere and dates where one of you decides to give the other a second date just in case but realize that it’s not going to work. Rejection, as much as it may sting at first, is part of the game. Welcome to dating; wear a helmet.

But here’s the thing: rejection may suck, but it only has to suck as much as you let it. Not investing in the importance of each individual date at the get-go is key. That first date is like the first audition; you’re trying to see whether this person’s worth making it to the next round. If they’re not… ok, cool, there’re others out there, time to go see how they stack up. I can count the number of people who’ve ended up in long-term relationships with the first person they ever dated on the fingers of one foot.

Your brother has a lot of dating success because he goes on a lot of dates. Like shooting a shotgun, the more lead you throw out there, the more likely you are to hit something. Go on a lot of dates, you’re more likely to find people who’re worth dating - or, in your brother’s case, who’re up for sex on the first date.

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Yeah, you’re not entirely sure what you’re doing. Neither is 99% of the population. Every first date is a lot of fumbling in the dark and feeling around, trying to see how much of you meshes up with how much of them. The less you worry about being perfect and more just about trying to connect with them, the better you’ll do.

Now, I’ve written a fair amount of best practices when it comes to dating in New Game +, and it’s worth your time to check it out - if only because it may help to have a blueprint to follow. But don’t worry if you’re not Studly Good Night with his smooth moves. There’s a reason why the term “adorkable” was invented. Grant Gustin’s Barry Allen is the pinnacle of awkward, but his earnestness and sincerity is what gives him so much appeal.

Put yourself out there and go on more dates. That’s how you build your experience points. You’ll find your success rate will go up and find the people who you’re compatible with. And of those, you’ll find someone that you have a genuine connection with, along with everything that comes with that.

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Good luck.

Hi Doctor!

I’ve been an avid reader of your posts—I’ve read a lot about your self-help posts, and they’ve genuinely helped me through a tough time, and help me fix my negative frame on things. But one thing I’ve struggled with recently is the fact that I have a rough time getting close to guys.

Here’s a little context. I’m a gay male, and am currently finishing up high-school, and I guess that you might venture to say that I may simply not connect with them because I have a predisposition towards feminine things, but I feel like that isn’t the case. I tend to crack bro-ish jokes, and I find myself laughing at what is usually considered crass.

However, one thing I’ve noticed is that my male peers have become less acquainted with me as of last year, and I’m not too sure whether this was due to me coming out or because of puberty pronouncing gender roles more firmly, as back then, I was actually very popular with guys and girls.

As a result, I’m always somewhat nervous around guys, and very self-conscious about what I say. I try to “tone down” my gayness, which sounds very conservative, or what-not, and I don’t know if it’s counter-intuitive. I’m not sure how to be myself around masculine bro-ish guys anymore, and it’s chipping away at my self-esteem.

Maybe it’s also worth noting that my school is casually homophobic. Like, I reckon an upwards of 90% of students would support gay marriage, but a lot of students tend to exhibit a lot of expectations of how a gay person should stereotypically act, and I’m afraid that I may have internalized it, leading to unnatural, janky conversations, or that it might simply that their casual homophobia makes it so that they’re averse to talking to me.

Should I learn to embrace myself more in front of them? Is there a certain trick to becoming a guy’s guy? Or are they just homophobic

Unsurely Insecure

Alright, UI, I want you to keep in mind that I’m a straight, cis guy. As a result, I’m not going to have the same perspective that a gay man my age might have, so take my advice with suitable amounts of salt.

So with that being said: I think there’re two things going on. First is that your friends may feel a little uneasy around you because they’re into terra incognita now that you’re out. Some may worry that you’re going to hit on them. Others may not be sure what to expect from you—like you said, a lot of your classmates are casually homophobic, and if you’re not falling into their idea of a stereotypical gay man, they may be confused. Still others may worry about saying or doing the wrong thing and have decided it’s easier to avoid you. And some of them may be dicks who don’t like gay guys.

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The second thing is that your own discomfort may be affecting them, too. Feeling uncomfortable and awkward can lead to others feeling equally uncomfortable. A lot of people tend to take their cues from the folks around them—if one person is at ease, the others tend to follow.

So what should you do? Well, in an ideal world, I’d say that the best thing you can do is start being your authentic self, whether that’s bro-ish, campy or whatever you might be when you’re comfortable. Keep in mind: you may well need some time to figure out who that is. Now that you’re out, you may need time to find your level, and that may necessitate some trying out different personas, as it were—just like most people do during high-school. Don’t turn down your gayness if you don’t need to; after all, straight folks aren’t turning down their straightness. It’s part of who you are.

I say “in an ideal world” because I don’t know if that casual homophobia you mention might put you into actual danger. But as long as you feel safe, be your out self and let others deal with it. Realizing they have a gay friend may well make some of these folks reconsider how they talk and think about gay men and women.

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And should it turn out that they’re just homophobic jerks… you’re almost done with high school and college is right around the corner. You’ll be entering a new world with new friends to make and new experiences to enjoy soon enough.

Good luck.

Hey there, Doc.

I need some advice about a complicated situation. It isn’t exactly about a romantic relationship, but I feel like you’d have some good advice for me.

Let’s start with the context. I’m a gay man and I have a friend who was and may still be attracted to me. We both are kind of flirty, but I’m only flirty around people I’m comfortable with that I’m not interested in in a romantic sense (aka I only flirt with my friends), but his flirtations are at the very least semi-serious. So we flirted a bit with each other, although he flirted with me far more often than I flirted with him. Anyways, there was a bit of a mutual attraction, which, looking back, was probably just because he was the only gay guy that I interacted with regularly at the time – I guess it wasn’t because I was attracted to him, but because he was there. Suffice to say that, after one particular interaction, any attraction on my end was wiped out pretty quickly.

I tend to be very frank and open when it comes to any discussions of sexuality, mostly because of a lack of a filter and a casual attitude about the topic, so my close friends end up learning a lot about me in that regard. Anyways, so I’m out with some friends, including the guy in question, and he ended up saying things that went a lot further than anything he had previously said to me. It was completely unexpected. Let’s just say the things that he called me while whispering in my ear were the kind of things that you don’t call someone without prior negotiation. On top of that, they were things that I am really not into, so that made me even more uncomfortable. Sure, the topic of BDSM had come up in conversation, but we weren’t anything but friends – we weren’t dating, we weren’t fucking, we weren’t anything but a possibility at the time. It made me really uncomfortable and it takes a lot to make me uncomfortable. In essence, I felt that several lines were crossed.

So I avoided being alone with this guy, avoided any touch other than a hello hug, even avoided sitting next to him. Obviously, I didn’t trust him; I still don’t, not that I’ve actually told him this. But we’ve been getting closer again, as friends. I don’t know if he’s still interested in me, but that’s not a thing that’s happening, not after that fiasco. But we’re still friends. But he’s still just as physically affectionate with me as back then, and I don’t like it – there’s still those times where he kisses my neck when we hug, or the butt-grabs. In the case of the latter, it’s something that isn’t uncommon among my friends, but it’s different when it comes from him versus when it comes from, say, one of my female friends. Neither of the two things are reciprocated, nor are they wanted, if I have to be frank. Honestly, I’m not even comfortable being close to him unless it’s the typical hug-as-greeting, which probably says a lot about what I think about him.

So here’s my question, Doc: how do I go about establishing new boundaries where there weren’t any? I want to salvage this friendship, but I don’t want the other things that seem to come with it. I don’t really want to say “You went too far once, so now everything is too far if you’re doing it.” or “We’re friends and all, but please don’t touch me.” What are your thoughts on my situation?

- Too Far

If you’re that uncomfortable with him now, I’m kind of wondering why you’d want to salvage the friendship. But hey, if you’re cool with him being in your social circle as long as he keeps his hands to himself, then I’m cool with it too.

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You establish new boundaries by letting your friend know that those boundaries now exist. The fact that you were flirty—whether you were flirting with intent or just for fun—doesn’t mean that you’ve given up your bodily autonomy. Being friends doesn’t give him the right to make you uncomfortable. The fact that you let other people hug you or play grab-ass also doesn’t mean that everyone gets the same privileges.

So, like you said: tell him “hey, please don’t do that” when he gets handsy. First time’s a warning. Second time is a very serious “No, I told you not to touch me.” Third time is a “Get the fuck off me or you pull back a stump”. You don’t need to explain or justify things; you and you alone get to decide who has the privilege of casually touching you. And if he can’t accept that or puts up a fuss, then it may well be time to reconsider your friendship with him.

Good luck.


How was your first dating experience? How long did it take you to get into your dating groove? Share your thoughts and experiences in the comments, and we’ll be back in two weeks with more of your dating questions.


Ask Dr. Nerdlove is Kotaku’s bi-weekly dating column, hosted by the one and only Harris O’Malley, AKA Dr. NerdLove. Got a question you’d like answered? Write doc@doctornerdlove.com and put “Kotaku” in the subject line.

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Harris O’Malley is a writer and dating coach who provides geek dating advice at his blog Paging Dr. NerdLove and the Dr. NerdLove podcast. His new dating guide New Game+: The Geek’s Guide to Love, Sex and Dating is out now from Amazon, iTunes and everywhere fine books are sold. He is also a regular guest at One Of Us.

He can be found dispensing snark and advice on Facebook and on Twitter at @DrNerdLove.