​Ask Dr. Nerdlove: How Do I Become 'Boyfriend Material'?

What's up, Kotaku? Welcome to the latest installment of Ask Dr. NerdLove, the only dating advice column that knows how to help you max out your social links with the Major Arcana of your dreams.

This week, we've got questions of how to make the transition from "friend" to "boyfriend" and handling the fears of taking your online flirtation into the real world.

Let's do this thing.

Dear Dr. Nerdlove,

I'm a complete failure when it comes to relationships in general, and never really dated in life, despite being almost 25 years old. With that said, and after more than 3 years trying on OkCupid, I actually somehow not only got a reply or two, but actually developed a nice conversation that led to becoming facebook friends and (last weekend) we even met up for some random walking around and talking for an hour or so.

This is by far the farthest I've ever got on any relationship with a girl, seriously. And that's my issue here: I have absolutely no idea how to proceed from here. I can't even say I have any idea if she's interested in me as a "friend" or anything else. From our usual conversation, plus the day we hanged out, I can be pretty safe she doesn't hate me or anything, despite our conflicting taste in anime (heh), but now I don't know how to keep this going and potentially turn it into a romantic relationship. What's the next step from here? Should I quickly call her out to do something more...date-like? Should I wait sometime before calling her to do anything else? Should I wait and see if she shows some interest? I'm completely lost here, Doc, and I don't want to miss this chance because who knows when / if this will ever happen again.

Thank you for reading this.

Living In Oblivion

Before we get started, if you've been using OKCupid for 3 years and getting next to no responses, you may want to tweak your profile a little.

But beyond that LiO, you have two issues I see all the time in my fellow geeks.

First of all, you're dealing with what's known as a "scarcity mentality" - in this case, the belief that amazing women (or men for that matter) are a limited resource and every rejection is a step closer to dying alone, unloved and unmourned.

It's a deceptively easy mindset to slip into; when you haven't had much success in dating, it can feel like you can count the number of potential partners on the fingers of one foot. And to make matters worse, it becomes a self-perpetuating cycle. You see, when you have a scarcity mentality, you tend to treat each potential date as your last, best chance for happiness… which leads to issues like approach anxiety, extremely needy behavior and - my personal favorite - Oneitis. As a result: you move too fast, push too hard and cling too tightly… and end up creeping her out or pushing her away. And so the cycle continues.

The way to break the scarcity mentality is to cultivate an abundance mentality - the understanding that there are literally millions of incredible women out there and that any single rejection just puts you one step closer to finding someone who's right for you.

The first step is to recognize that rejection isn't inherently bad. At its core, rejection means either a matter of presentation or a matter of incompatibility… and getting feedback about that stuff is doing you a favor in the long run. Yeah, it sucks - I've been rejected more times than I can count - but you can take time to examine what went wrong and what to do differently next time. Because there will be a next time.

So, don't treat this woman as your only chance for love - that's a lot of pressure to put on someone you barely know and it's going to scare her away.

But what do you do? Well, this is the second problem: you're being too passive because you're trying to eliminate all risk. You don't want to make a move unless you're 100% assured that you're going to get the best ending, and that's a recipe for losing out on a potentially great relationship. You have to be willing to lay your cards out there and tell her you're interested in dating.

Can I let you in on a little secret? That's part of what she's looking for, too. You met this woman on an online dating site, not an online friending site. She met up with you because hey, there seems to be a bit of chemistry there, why not see how you two do in real life? And now she's a little confused because you mostly walked around and talked. Which can come off as you telling her you're not interested in more than friendship. As a result… well, she's going to start seeing you as a friend.

You have to put yourself out there and show your interest. You have to be willing to flirt a little, to show her that you like her as a potential relationship, not as a platonic friend to get together and debate whether Beyond the Boundary owes a debt to Devil Hunter Yoko and El Hazard. You have to take a risk because you're never going to actually get anywhere unless you do. Playing it safe just means that you're going to be waiting a long time because you will never have a 100% guarantee that you're not going to get rejected.

So, here's what you do: you call her up and take her out on a date. Not "get together to hang out". Not "do something, some time." Tell her you had fun with her but you'd like to go on a proper date this time and there's this amazing event/show/restaurant/thing you'd love to take her to.

And here's a tip: pick something active, something that will get you interacting with each other and get your heart pounding a little. Personally, I'm fond of something a little competitive - go-kart racing, for example. But whatever you do: make your move. Even if you get shot down, knowing that you were able to put yourself out there and take that risk puts you in a better position to try again next time. And there will be a next time.

Good luck.

Dear Doc,

I'm having trouble with online dating. You see, I am a male-to-female transgender person. And the small town I live in has no one remotely interested in that kind of thing. So for a long time now, I've turned to the world of online dating to sustain my need for affection. However, all my relationships seems to end the same way. Either I lose touch with the person or I found out things about their personality I really don't care for later down the line. I am always the one who has to keep up with the relationship. Starting texts, IMing first, bringing up issues; all that. I'm simply tired of it now and wondering if I should just give up completely. I have no trouble finding women that I am interested in and who are interested in me in return. But it becomes a struggle when you feel like you are the only one in the relationship.

I also have this great fear of meeting them in person. I feel like the persona I put on online (a more open personality) won't translate well to real life. I try to explain that I am a shy person in real life. But if given the time I become more open as I get to know a person. My fear is when they meet me I won't be the person that they've come to love. And maybe I won't be pretty enough for them. This has caused me to hold off meeting a lot of people. Only a few I have talk to and made plans to see. But like I said above, something always happens to end the relationship. What should I do?

~ Lost

Hey Lost,

Online dating can be frustrating, especially when you're just starting out. One of the trickiest aspects of online dating is that we don't have a lot of the same unconscious factors that control our interest in people. When you're at a party, for example, you have a number of opportunities to observe people and pick up on the subtle clues that help determine how likely you are to be compatible with them. You can see them interacting with their friends and notice that they're rowdier than you'd like, or you see them being an asshat to somebody else. You might hear them tell a joke you find offensive. They may douse themselves in Axe.

In online dating, you don't have those clues. As a result, you end up messaging a lot of false positives - people who seem good on paper, but with whom you just don't click in person. That's just part of the dance, unfortunately. Womp womp.

Now, before I get into the heart of the matter, I want to preface my advice by saying that I'm a hetero, cis-gendered guy, and I can't speak to the entirety of your experience. You may have some questions or concerns that I won't be able to answer. However, there are a lot of good and helpful resources for trans people there where you can find more specific advice and support. GAAD's website has a pretty solid list of resources to start from.

It's entirely understandable that you're afraid of meeting up in person. We're able to curate our presence online - we have control over our persona and our appearance in a way that we simply don't in real life. When we chat over IM or email or text, we have more time to craft a response or consider what we're going to say and have less of a risk of blurting out the things that make us want to dig a hole in the ground, jump in and pull it in after us. And if we've put that much work into looking goddamn amazing on Facebook and Instagram and Twitter, how are we supposed to match up when people meet us in real life?

But part of online dating is the dating part… and that means having to get to know people in the real world. We're on dating sites in order to actually meet people, and if we take too long to meet up in person, it's very easy to lose the emotional momentum and have things just peter out after a while. I suspect that this is how you're ending up losing touch with people; they're hoping to meet this awesome person they're interested in and if it just keeps not happening… well eventually, they decide it's time to move on and start pursuing potential relationships with folks who do want to meet.

To be fair: you've got reason to want to be cautious and to want to do your due diligence when you're talking with potential dates. Taking the leap from online to in person when you're trans can be huge. You have legitimate worries about your physical and emotional safety that need to be taken into account. So you should make sure that you feel safe, especially when you're planning on meeting in person, and pick a safe, public environment in which to meet up for the first time.

But there does come a point where you have to be willing to pull the trigger and suggest meeting up in person to find out if this emotional chemistry you have together translates into physical chemistry too.

My general rule of thumb is that if you've had three solid messages back and forth, it's worth swapping numbers and setting up an audition date - meeting up someplace public and neutral to feel each other out and see if there's enough interest (and safety) there to meet up for a real date. If you're wanting to be a little more cautious, you may want to have a few more back-and-forths before meeting. On the whole, though, meeting up sooner rather than later means that you're less emotionally invested in making things work out; if it turns out that they don't dig you or you don't dig them... well, it sucks but it's better to get it out of the way early rather than let it build up into something huge first.

All those fears you're feeling about not measuring up to your online persona? Totally legit. You're afraid of being hurt or being disappointed, of making yourself vulnerable and getting slapped down for it. But unfortunately, you can't find love and be completely emotionally safe at the same time. Dating means inviting a certain element of risk. There's always the chance that we're going to get rejected. And it sucks, believe me. But not only is rejection not the end of the world, it's something that can make you a better person in the long run. And at its core, dating means gambling that the rewards - meeting somebody awesome - are worth the risk.

Unless you're night-and-day different online than you are in person, then what you're really doing online is showing who you are when you're comfortable with someone. It's still you, just more of a preview of who you are after you've gotten to know someone more in person.

And if they're worth meeting, they'll totally get that.


Did you make the leap from friend to boyfriend? Have online dating tips that never fail? Share your thoughts in the comments section! And we'll see you in two weeks with more of your questions!

Ask Dr. Nerdlove is Kotaku's bi-weekly advice column for matters of the heart, hosted by the one and only Harris O'Malley, AKA Dr. Nerdlove. Got a question you'd like answered? Writedoc@doctornerdlove.com and put "Kotaku" in the subject line. Man, woman, single, married, he's got advice for everyone.

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. 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. Dr. Nerdlove is not really a doctor.

Top image from the Scott Pilgrim series.