Can You Date Someone After Being Friends First?

So You're Falling For Your Friend - Here's What To Do Next

The Dating Nerd is a shadowy figure whose whereabouts and identifying details remain unknown. What we do know is that he is really, really good at dating. He’s been on more dates than you can shake a lengthy bar tab at, and he’s here to help the average guy step his dating game up a notch -- or several.

The Question

Hi Dating Nerd,

I’m kind of in love with one of my best friends. And I think it’s possible that she feels the same way about me. Initially, things didn’t seem romantic, but the energy between us has changed over time. And I’m wondering: do you think it’s a good idea to pursue a friend? Do you think that can lead to a good relationship?

- Amorous Alex

The Answer

Hi Alex,

So I have a suspicion about this letter of yours. I’m guessing that what you want me to say is “yes.” That you should absolutely throw yourself at this girl, that the length of your friendship is no obstacle, that the desire in your noble, manly heart will conquer all. Well, if that’s what you want, I’m going to save you some time right now.

That is not my opinion. I don’t think that it’s necessarily wise to pursue your friend romantically. In fact, I think you would be risking a great deal, and the chances of reward aren’t exactly stellar. My recommendation, unless you’re zealously, unshakably attracted to this friend of yours, is that you sign up for a few online dating sites, buy a few new outfits, and play the field for a bit. There are lots of cool people out there.

This is not to say it’s impossible for friends to become lovers. It happens. And sometimes a friendship can provide a great basis for a really deep attachment. But that’s definitely the exception and not the rule. And I can do is tell you why that is, so you have a better chance of figuring out whether your situation might become one of those lovely outliers where you end up happily in twoo wuv.

Let’s start by taking a step back. So, generally, the iron law of male/female friendship, presuming that both parties involved are interested in the opposite sex, is that such friendships form because there’s a lot of mutual admiration, but no sexual attraction to fuel it. A typical scenario goes like this: You flirt with a cute girl at a party, and the conversation is amusing and maybe even profound, but after you hang out some more, in a situation where there’s no alcohol around, it turns out that there’s absolutely no sexual chemistry. About 90% of the time, that’s how it goes.

RELATED: The Surprising Benefits Of The Friend Zone, Revealed

And, unfortunately, attraction levels are usually fixed. Which is to say, if someone didn’t want to make out with you in some previous era of your life, chances are they don’t want to slobber all over you now. You’ll probably find this to be true if you reflect on your own personal experience. Go on Facebook and look up someone who expressed unreturned interest in you, say, four years ago. Are you more interested in her now? Maybe marginally -- maybe she has a better fashion sense now; maybe a more impressive career. But your basic attitude probably hasn't radically transformed, right?

Of course, there are rare exceptions here. Occasionally, people can go up a few rungs on the attractiveness ladder. Maybe you do a Chris Pratt and radically change your physique. Or you do a Mark Zuckerberg and go from being a random nerd to a powerful rich person. But most of the time, adult people are roughly as attractive now as they’ll ever be. Personality, which is such a huge factor in attraction, tends not to change drastically. Shy people stay shy. Outgoing people stay outgoing. Tortured artists, power-hungry maniacs, sports bros -- they tend not to become drastically different people.

But maybe you’re still reading, because you’re one of these exceptions, and you’ve noticed that your longtime friend’s gaze is lingering on you in a way it didn’t used to, and your hugs are suddenly more prolonged and tighter than they used to be, and, suddenly, you’re both making a lot of excuses to spend time alone together. Great! Very happy for you. But you still might be facing an uphill battle here. Why? Well, asking your friend out in an appropriate fashion is really really hard.

Compare the situation you’re in to a more mundane romantic scenario -- like, say, a first date. People regard first dates as scary, but really, they’re not so hard, because there’s a great deal of default social frameworks around them. Everybody knows what’s going to happen. You check each other out, figure out whether there’s some sort of spark, and, crucially, you know that you’re probably going to kiss at the end, if things go well. So, when you go for her face at the end of the night, at the very worst, you’ll get confronted with a cheek.

That’s not the case with you. You can’t just randomly decide to make out with your friend, or go in for a kiss at a random moment, because, even in a moment that feels pregnant with a lot of romantic tension, that’s not what’s on the script. If you do, and your friend isn’t expecting it, and it’s unwelcome, this might even constitute sexual harassment. Not because that’s your intention, but because you might have read the signals wrong -- we’ve all been there -- in which case you’re just initiating unwelcome physical contact. Not good.

What this means is that the best you can do is have a hideously awkward conversation. Terrible, I know. You’ve got to sit your female friend down and say, “hey, I know this is a little weird, and maybe out of nowhere, but… as time goes by, I’ve found myself feeling more attracted to you in a way that’s not strictly platonic, and I was wondering whether you feel similar at all.” (Or however you would say the equivalent thing.) At which point, she either expresses joyful surprise, or cautious curiosity, or apologetic repulsion. And either your friendship gets taken to another level, or it gets killed off, or it somehow survives the awkwardness.

This is what you have to keep in mind -- that you might well be rejected. That it is, in fact, pretty probable that your poetic advances will be totally unappreciated. And if this is the case, it’s absolutely vital that you be a gentleman about it. Don’t whine and complain and try to change her mind by pleading your case. Remember: Your intense feelings towards someone don’t change the fact that they don’t owe you anything. You have to respect that this is her decision to make, and that you’re putting her in a pretty intense situation by baring all of that volcanic emotion that you’re carrying around.

If you still decide to go for it, in spite of all my cautionary ranting, I truly wish you luck.

Think you could use some dating help, too? Email the Dating Nerd at [email protected].