Is It Ever Okay to Date a Friend's Ex?

I hate to be the bearer of bad news, but the answer is usually no.

There is a possibility you can date your friend’s ex, but I don’t want you going into this with false hope. No is the default answer.

There are exceptions, though, which is what this post is about. Take these exceptions into consideration and then think about it. If none of these exceptions apply to you, take the default answer of no, don’t date your friend’s ex.

Enough time has passed.

First, figure out if enough time has passed. If the relationship only lasted a week and its been six months, you’re in the clear. If the relationship lasted two years and it’s been two months, you probably need to wait.

This is first and foremost for your friend and the person you’re interested in. You need to let them heal from the break-up. It’s difficult enough to heal when a relationship ends. If you start dating, you’re adding another heap of difficult emotions on top of those that need to heal. It’s not a good idea.

It’s also for your own reputation. If you date a friend’s ex too close to when they were dating, it looks suspicious. Other people might start to think stuff happened between you two while they were dating your friend.

You might respond to this “But it’s none of their business!” Okay, sure. They might be a bit nosy. But like it or not, relationships happen in the public eye and your friends will have an opinion on it. You shouldn’t obsess over what other people think, but you should at least care about what your friends think.

You are willing to let them find out from you.

If you want to date your friend’s ex, you need to be willing to tell them yourself.

You know your friend better than I do. How will they take it when they find out?

If I had to guess, they probably won’t be thrilled. They might feel betrayed or angry. You are probably tempted to avoid the problem altogether and let them find out on their own. This is a not a good move and will likely make bad feelings worse.

Because of your friendship, you have the duty to tell them yourself.

On top of that, if you are not willing to tell them, it’s probably a sign that you don’t want this relationship bad enough. Your friend’s negative emotions are a natural consequence of you choosing to date their ex. If you’re unwilling to face those consequences, you probably aren’t going to be willing to face other hard or uncomfortable things that happen in your relationship.

You are prepared to lose the friendship.

This is the hardest one, but you need to be prepared for this. Like I said earlier, you don’t know how they’ll react to the news. They might be angry enough and never want to speak to you again. They could say it's fine and slowly stop hanging out with you over time.

Whatever happens, you need to face the reality that starting this relationship could end your friendship with your friend.

So take some time to sit and reflect. How valuable is this friendship to you? How valuable is this new relationship? If you had to live your life with only one of the two, which would you pick?

It’s very possible you would pick the relationship over the friendship. But be warned, new relationships have the tendency to look better than they are.

If you meet these criteria, the answer might be yes. It is okay to date your friend’s ex. If not, reconsider the decision. There are real risks and consequences, so make sure you take those risks with discernment.