After reflecting on a short-term relationship with an awesome guy, I realized it was intense and fun …at first. I fell out of love with him just as quickly as I had fallen in love with him. And oh, yeah, we were friends for a solid four years first. So if you’ve fallen for your friend and are thinking about taking the plunge, here are the pros and cons of sleeping with – or dating – someone you’re already tight with.

Pro: You’re friends.

You already know you get along on a “friendship” level, which is important for any romantic relationship. That’s definitely a good thing! You have things in common and already enjoy spending time together, so there’s no worry that things will be awkward between you throughout your relationship.

Con: Um, you’re friends.

Dating a friend means risking your friendship. A week post-breakup, I think we’ll be able to be friends again soon, but I’m still not completely sure. I already don’t care about or like my ex as much as I did pre-relationship, which sucks. The situation also gets risky if you share mutual friends. Two of my buddies recently broke off a long-term relationship, and choosing sides has definitely changed a lot of the dynamic in our friend group.

Pro: You already know their friends/family.

This makes awkward introductions so much easier! In fact, it completely gets them out of the way. You’re already a part of their group, which makes things a lot more fun and totally easier than a relationship with someone new.

Con: You already know a lot about each other.

While you’re obviously going to learn new things about your partner once you start dating, you might already know too much about one another. Maybe you’ve known him since he was a kid and you can’t get that image of some embarrassing childhood moment out of your head. Or maybe you’ve been her best friend for so long that there’s nothing big left to learn that would otherwise make your relationship exciting. That’s definitely a bummer.

Pro: Less awkward moments!

You already love one another as friends, so that gets rid of a lot of the early relationship awkwardness most couples face. You know how to laugh around one another, so you can shrug off so many of those weird firsts. If he’s been your friend for years, chances are you’ve already seen one another blackout drunk, farted in front of one another, or chanced upon embarrassing yearbook pictures.

Con: It could still get awkward.

It’ll sting so much more if and when you guy break up. Everyone who mutually knows you will feel a little weird. In my situation, I had always liked my ex while he saw me as a friend until we hooked up. Once we started dating, I quickly realized we should have stayed friends while he began to fall hard. Now I’m sure we both kind of wish we hadn’t taken things further than a drunken adult sleepover or two.


If it works out, your romantic relationship with your friend could be amazing! I definitely think it’s worth the risk – depending on how close you are. In my case, I dated someone I wasn’t crazy tight with, so things shouldn’t be too awkward after some time and space. But if you’re falling for a BFF, consider being a bit more cautious. All is fair and love and war, but I’m not so sure about love and friendship.