You’re Not a Bad Person for Wanting to Date Your Friend’s Ex, But You Need to Do It Right

It doesn’t have to be a choice between romance or friendship.
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It doesn’t have to be a choice between romance or friendship.
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You didn’t plan it this way. You didn’t even seek it out. It just sort of happened. You’re into it, he’s into it, there’s some serious chemistry, and you might have stumbled upon something really special. There’s just one problem.

He has history with one of your friends.

Now, you’re faced with a most unenviable predicament: Walk away from someone who could end up being the love of your life, or put one of your friendships in jeopardy.

In discussing this topic with my female friends, it seems to me that men are especially experienced in dealing with this dilemma. Like it or not, we find ourselves appreciating our buddies’ tastes in women (what can I say, great minds think alike!). Say a friend of mine breaks up with so-and-so, and we run into her at a party. We end up having a great conversation, and try as we may, sometimes no amount of telling ourselves, “Pull yourself together, man! Don’t be an a-hole,” can prevent us from wondering, “What if . . .?”

In some ways this is perfectly natural. Guys and gals get to know their friends’ significant others in nonthreatening, no-pressure contexts and learn to appreciate what their friend liked about them. They likely have things in common and, even after the breakup, still share many of the same friends, and we’re all looking for love, right? This sort of stuff happens more than you might think.

People often have a bad opinion of pursuing friends’ exes. And there certainly are times when people who go down this path find that it really wasn’t worth it. But if you’re wondering how to go about dating your friend’s ex, and you think the pursuit might really have potential, don’t worry, you are not a terrible person. But you do need to make sure you go about this right.

Luckily, a woman can approach this in pretty much the same way a man does, and that’s where I can help a sister out. Take it from a guy who has been in this tight spot a time or two—there are three things you must do before moving forward with your friend’s ex.

Consider the problem.

Perhaps you’re thinking to yourself, “We’re all adults here. What’s the big deal?” Here’s the thing. Anyone who has had any sort of meaningful romantic relationship can tell you that—over it or not—it would be difficult for them to be around their ex. So even if your friend is “OK” with you dating her ex, you are likely going to see a lot less of your friend.

A buddy of mine recently mentioned that he might invite my ex to a party that we were going to and asked what I thought about that. I was honest with him and told him I’d probably be less likely to go if I knew she would be there. It’s not because I still had feelings for her. I just wasn’t jumping at the chance to be around her.

And that’s really what we’re talking about here. Breakups require space. And if you want to spend time with someone who has been “spaced” by a friend, that will very likely mean that you will then be spaced from your friend, too.

The question you need to ask yourself, then, is whether it’s worth it.

So, is it worth it?

We all know the difference between a fling and something more. A fling and something more is the difference between, “He’s kind of cute,” “It’s fun having someone to be with,” or “It’s certainly better than being alone,” and, “He’s so great; I feel like we really have a connection,” “We have so much in common,” or “I really think there could be something there.” This distinction is the most important factor in deciding if dating your friend’s ex is worth it.

Recently, my friend was telling me that he wanted to go out with his ex’s friend. But he also mentioned that there were other women with whom he’d like to go on a date. Why not go out with the other girls first? Seems like a no-brainer to me.

I hope we can all agree that our friendships are more important to us than a few exciting dates with the next best thing. And if so, tread carefully when spending time with someone who has a history with a friend, especially if you don’t really see a future with the guy.

That being said, if you find yourself drawn much more strongly toward the ex, then it’s worth thinking about. If one of your biggest goals in life is to find someone to marry, I certainly wouldn’t dismiss something like that without some serious consideration.

You never know unless you ask.

Here’s the key to handling this situation well: You’ve got to ask your friend. Before it gets serious. Before it even gets semi-serious. Ideally, before anything really happens. Like even before a kind-of date.

It might be the case that dating this guy would completely ruin a friendship, and you’d have to move to another country. Or it might be totally fine. Or it might be somewhere in-between. But unless you ask, will you ever know?

Why ask? Why not just tell her that you’re going to date her ex? Admittedly, it’s mostly semantics. But it matters, nonetheless. I know men typically like to have control over situations or at least feel like we have control. I imagine that most women like to have the same sense of consent. But either way, think about it: Would you rather be asked about something or told that something’s going to happen a certain way? At the very least, it shows her the respect that she deserves given that you have had a relationship.

By asking, you let your friend know that you care about the friendship at stake. Let’s be honest, she’s probably not going to be thrilled about it, however it happens. But the longer you wait before you take the initiative and bring it to her, the worse it’s going to be.

Extenuating Circumstances

Of course, not all situations are created equal. There probably are some lines that can’t (or shouldn’t) be crossed. Sure, it might make for good cinema, but at what point are you willing to end friendships, complicate entire friend groups, and potentially divide families? It’s a good idea to go into any romantic affair with eyes wide open. The key to making a prudent decision here is to keep an emotional distance until you have made a conscious decision to move forward with your friend’s ex.

Ultimately, we’re all in this one together. We all want to be happy, and most of us are looking for someone with whom to live happily ever after. If you go about it the right way, many of these complicated relationships can, at the very least, be given a shot. The most important thing, as is true in most cases, is to be proactive, communicate clearly, and be thoughtful and considerate, especially when there are strong emotions involved. And remember, it never hurts to ask. As a wise man once said, “So, you’re sayin’ there’s a chance?”