I love the idea of forming a friendship before starting a relationship with someone. I like to know all the potentially-deal-breaking details as early on as possible, and if those details make me uncertain, it’s nice to have that “buffer room” that the so-called friend zone provides. There’s only one big problem with this idea: Once you break up, it’s going to be really awkward because you’re still going to see each other on a fairly regular basis. The realities of being in the same friend group as your ex are difficult, painful, and of course, sucky.

(As a side note, these are often the same reasons why I advise against dating a coworker – things can get weird, really fast.)

Wondering what the specific reasons that make up that bigger problem might be? We made a list.

Your friends are going to talk to her.

And of course, she should still talk to your friends, if you were all friends together. In fact, it’s highly unethical to ask your friends to choose between you and your ex – especially if you guys met through them. (I know, it’ll be tempting to ask, if she did you really dirty – but if you actually care about your friends at all, you’ve got to leave them to their own opinions of her.)

Your friends are going to talk about her.

Whether your friends still talk to your ex or not, you better believe that – if they met her – they’re probably going to talk about her. In most cases, there are two categories of talking about a friend’s ex: Either they remind you of funny stories, or they trash talk her. Either way, she’s going to be on your mind quite a bit.

You’ll be tempted to check up on her.

As much as we’d like to pride ourselves in our ability to keep our distance, it’ll be a whole lot harder if you know that you can ask your friends what’s going on in her life. Even if you never do actually ask, the temptation will make you feel guilty, and there may come a time when you’re not able to resist.

She’s got an “in” to keep tabs on you.

If your friends are friends with your ex, and they’re telling you what’s going on in her life, chances are it goes both ways. Of course, we’d like to hope our friends wouldn’t gossip about us, but in many cases, someone who gives into the pressure to gossip will give in more than once.

You’ve got an “easy out” when it comes to being anti-social.

Most of us are pretty bad about falling out of touch with our friends when we’re seeing someone. But if your ex is in your friend group, this antisocial behavior can continue even after you’ve broken up. In an attempt to not see her (thereby avoiding your feelings), you also don’t see your friends, because she might be there. You rely on your friends coming to you all the time – and that’s not a very fair expectation to them.

You’re still going to see her.

It’s psychologically impossible to get over someone if you’re looking at their face three times a week, but you’re going to want to spend more time with your friends after a break-up. Most of the time, your friends are probably going to try to keep the overlap to a minimum, but it’s not really fair to push your friends to choose one of you over the other. (Personally, I tend to side with whichever friend didn’t make me choose.)

You’ll probably end up hooking up.

If the two of you are hanging out together on a regular basis, you’re probably going to end up having “ex sex”. You tell yourself it’s just to get some closure, or maybe for old time’s sake, but you end up destroying whatever progress you’d made in moving on. There’s nothing inherently wrong with this, but if it hasn’t been long enough for you to fix the compatibility issues you had, you’re just prolonging the inevitable heartbreak.

It’s going to be more difficult to move on.

Even if none of the other factors involved end up being appropriate here, the pain of the break-up is going to be extra tough, because you’re losing not only a lover, but also a friend. Break-ups within the friend circle can be incredibly awkward and painful, but that alone shouldn’t deter you from dating a friend. If the connection is there, and the feelings are mutual, you know what they say – it’s better to have loved and lost than to never have loved at all!

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