Ask Dr. Nerdlove: How Do I Become ‘Boyfriend Material’?

Ask Dr. Nerdlove: How Do I Become ‘Boyfriend Material’?

What’s up, Kotaku? Welcome to the latest instalment 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 behaviour and – my personal favourite – 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 recognise 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 favour 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 have 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 will 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? [email protected] 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.


  • I know this is a bit extreme, but to get over scarcity mentality some mates and I started walking up to girls and telling them “I just have to tell you your the most beautiful woman I’ve ever seen.” The reactions ranged from polite dismissal, right through to a mate of mine getting a straight backhand (which was a bit extreme). It was never successful. Ultimately though, it intended to toughen us up a bit. In the end, I think that you can increase you success with women just by approaching more of them, but you have to be able to handle rejection well.

    • “I just have to tell you your the most beautiful woman I’ve ever seen.”

      That’s all most people need to do and it totally works. Every single one of my relationships (where I approached them and not vice versa) has been initiated with a simple “Hi, lets talk.”

      People sometimes complicate this needlessly. Sure there will be plenty of failures, but in the end if you persist you’ll find someone you like that will reciprocate.

      • I wouldn’t ever say “you’re the most beautiful women I’ve ever seen” though, because that’s bullshit and people can sense it. Maybe instead try being honest and say, “hey, I just really wanted to talk to you!”

        • Honestly, it almost doesn’t matter at all what you say. If someone is available and likes you, it’s largely irrelevant. I got together with one of my exes after I said “wow, you’re hot”.

          “you’re the most beautiful women I’ve ever seen” is a bit tacky though.

          • Yeah – it really doesn’t matter what you say. I was OK with the ladies, and my mates always wanted to know what the trick was. There was no trick – I’m loud, funny, and polite. I would usually just introduce myself.

            I did have a mate that used to pick up girls by asking them: “Hey, want to see my bed, its on milk crates.” It was weirdly effective.

          • The most beautiful woman you’ve ever seen? Not bad. I prefer, “The most beautiful woman that I’ve seen today.” You can then qualify that with things, “But I haven’t got out much,” or, “…and I’ve been in the CITY.” They might teasingly reply, “What, only today?” and you can engage right back if they’re trying to continue a conversation, sure. That’s win, right there, don’t look a gift horse in the mouth.

            But most of the time, the key is just walking away. You’ve only said it because you were compelled to comment, like anyone might be compelled to exclaim when they witness some truly impressive work of art. They’ll feel better, and hopefully you’ll feel better too. The world can probably stand to have more moments of random compliments. Even if it’s just some guy’s nerdy video-game t-shirt, or you notice those glasses really suit that girl.

          • The world can probably stand to have more moments of random compliments.

            I completely concur dude! 🙂

          • Plus, by walking away you’re then the cool guy who said something in passing and made them feel good about themselves instead of the creepy guy who harassed them!

        • That was the point though – none of us had ANY notion that this would work. The whole idea was to get rejected by girls, without being obnoxious or deliberately making them feel bad or something.

    • I don’t think this is a good idea personally. If anyone ever approached me like that I would feel intensely uncomfortable, and really, it doesn’t show much respect if you make someone feel that way. I’m sure its not your intention, just something to be aware of.

      • I would say 95% of people seemed to really appreciate the comment. We did it non-indiscriminately too, from classically good looking girls, through to much older women who maybe hadn’t been complimented much lately. The goal was to get used to talking to strangers (and getting shot down too), not to make them uncomfortable. I think the fact it was such a stupidly over the top thing to say made it pretty clear we weren’t trying to pick them up.

        • Ahhh that’s pretty cute. I was thinking it was along the lines of ‘You’re beautiful! Give me your number!’ Which is a bit weird. Thanks for clearing that up 😛

      • Unless you’re pre-approved with social status or amazing looks, ANY contact up-front can make people feel uncomfortable. It’s not a good reason to not make the approach.

        If people get uncomfortable because someone came up and told them they were pretty or ask them for their number or a date, that’s their fault, not anyone else’s. They should be taking the attitude of being flattered and rejecting gracefully, then go about their lives as normal.

        One of the huge problems with geeks and nerds never making an approach AT ALL is because they’re way too hyper-sensitive to this concept of asking someone out or complimenting them as some kind of offensive act. It’s not. It can be momentarily awkward, but it’s better done than not done, or than the alternative of trying to collect enough data through observation to ensure that they know enough about the person to make an appreciated approach. THAT is textbook creepy, but what’s a sensitive nerd to do? Mind-read so they know that they are an acceptable person to make a come-on? Only ever ask out people they’re already familiar with?

        These are losing propositions. We need to get away from the idea that a moment of genuine human contact, of sincerity OR flattery is some kind of form of abuse because ‘it made someone uncomfortable’. People need to get over that. It is in no way, shape, or form ‘disrespectful’. There are disrespectful ways to do things, but just approaching? You don’t respect someone by treating them like a porcelain figure to be tip-toed carefully around and never breathed near for fear of breaking them.

        • the alternative of trying to collect enough data through observation to ensure that they know enough about the person to make an appreciated approach. THAT is textbook creepyWell, shit.


          • I don’t like the word ‘creepy’ because it’s basically code for, “Behaviour I would accept from someone I like, but not from you, and you should know your place enough to know the difference.”

            But yeah, that’s what the girls call creepy.

          • I dunno, creepy is creepy. Even if a guy I liked was scrutinizing my every move… I wouldn’t like them anymore. Creeperville!

            Also, I have responded to your above comment, but its TLDR and apparently needs to be approved 😉

          • Yeah, it happens. Happens for huge posts, posts with more than one URL in them, for new posters, and anyone who’s been downvoted into oblivion a few times. I hear you can often get around it by editing the post (with no real changes) and saving. Never tried, myself.

        • I think its all in the context (Which Magus kindly cleared up above).

          I don’t think complimenting or asking someone out is offensive most of the time, but there is a respectful way to do it, imo. Compliments with no intention is fine, I compliment my friends and strangers (yay customer service!) but doing it to get someone’s number or for an ulterior motive is what makes me uncomfortable- Magus cleared up it was purely innocent, which is nice, and yay for more positive influences in the world. But if you’re a stranger trying to get my number… yeah, me being uncomfortable is justified- you don’t know me!

          If you want to ask someone out, get to know them, be their friend. I find it personally uncomfortable when strangers have approached me on the street. I’m not sure if its something you can relate to, but as a female, being approached by a male, when you’re alone, can be intimidating. It puts us in an uncomfortable situation where we are unsure how this stranger is going to react if you say no. I have had someone follow me in the car and yell out ‘Slut’ to me as I walked because I refused to get in the car with them. Obviously not everyone is like this but its just a sad reality.

          I hope I’ve worded this right- its hard to explain without sounding all ‘AMG DAMN THE MAN’ because I truly don’t think that. But I would hope you understand it is not my fault for feeling uncomfortable when a stranger approaches me on the street, let alone a group of males like the above scenario.

          If you are going to ask someone out it should be in a comfortable environment where there’s no pressure either way to say yes or no.

  • Sometimes I find Dr. Nerdlove a tiny bit limp. A bit too prissy, if you will. But there is just pure gold in here that every nerd should internalize.

    “The first step is to recognise that rejection isn’t inherently bad. …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.”

    Even the hardened, most manipulative, got-everything-going-for-them professionals at this shit reckon on a 75-90% success rate at absolute best. EVERYONE gets rejected. Even super-stars. You and me not resorting to trickery or manipulation, just maybe a cute hook to get a conversation going? Much, much, much higher strike rate. And that’s OK.

    “You met this woman on an online dating site, not an online friending site.”
    “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.”

    I see my friends doing this ALL THE TIME and I just want to shake them. Shake them so hard to snap out of it.

    Ah screwit, even more things to quote… Forget it. The whole letter-response is pretty much perfect.

    Take risks, don’t fear rejection, make your intent very clear very early and don’t be ashamed of it, take the lead, don’t wait for perfect signs.

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