(Full disclosure: I use the term ‘ex’ here loosely, referring to any guy a girl has spent any time liking, hooking up with, going on dates with, etc. I know some try to justify their actions by saying things like, “Well, technically they didn’t officially date.” Doesn’t matter. You don’t need to have an exclusive, labeled-relationship to have feelings. )
Dear Girl Dating Her Friend’s Ex,
I know that, like every woman, sometimes you worry you’re going to be single the rest of your life. We all have those feelings, even when we know it’s irrational. I also know sometimes you just can’t help who you like. However, I am here to tell you that these “feelings” are not an excuse to be a shitty person or friend.
You may not be able to help who you like, but you can help how you choose to handle it. If you choose to hook up with or date someone your friend has any bit of history with—however long ago or serious it was or wasn’t—you don’t deserve her friendship. Even if she is dating someone else, or hardly talks about him anymore, there is nothing to excuse intentionally doing something you know could bother her.
If you’re going to do it, don’t have the audacity to try and excuse it by saying, “Oh, I really didn’t think you would mind.” Not only does that make you conniving, it makes you a liar. Of course she would care; you are just capitalizing on the fact she maybe, probably wouldn’t admit it. And why is that? Because you know “she has no right?”
Girls are constantly told we’re crazy and overly emotional. When you ask her for permission—instead of letting her just find out from friends and assuming the position of, “Maybe if I just act like this isn’t a big deal, she will too.” )—chances are she will say she doesn’t care. This is the equivalent of telling a guy we’re “fine.” We’re not fine, and she does care. But her fear of looking like a psycho will prevent her from admitting it. And I think deep down you know that.
She has two options; she can tell you she does care, and look like a clingy, pathetic girl who hasn’t move on with their life; or she can swallow her pride and say go for it.
If she tells you it’s okay, that is still not reason enough to do it. Aside from the fact that she probably really does want to be okay with it, doesn’t mean she is, nor should she have to be. If she tells you to go for it, she has to watch you try to make things work with someone who didn’t work with her.
I don’t care if we’re talking about someone she casually hooked up with on-and-off throughout college or was her boyfriend of 3 years, if she had an intimate, romantic or flirty relationship and it didn’t work out, it hurt her ego.
Regardless of the reasoning or details, it didn’t work out with them because it wasn’t a good relationship. Do you know what feelings are never associated with not-good-relationships? Warmth, happiness and positivity. The chances your friend is 100% okay and happy about you dating him are about the same chances that this is going to end well for you—slim to none.
Even worse is if this is someone who caused her pain. Not only are you excusing his behavior, while dismissing and minimizing her pain, you’re setting yourself up for that kind of treatment too.
Sorry, but the odds are not in your favor. No relationship is healthy enough to last long-term when at least one of the participating parties is insecure enough to choose hurting someone they love just to feel validated by a relationship.
She might pretend it’s fine, but your friendship will never be the same again. You better hope it works out, for your sake—otherwise you are going to have one less shoulder to cry on. You broke that trust. To her, whether she admits it or not, and probably to some of your mutual friends, you are always going to be that person. You showed you were capable of doing that.
So go ahead and have your fun. But don’t expect those nagging questions in your gut, asking you ‘does this make me less of a person?’ or ‘is this going to bite me in the ass?’ to subside anytime soon.
You already know the answer.