Is It Okay To Date Your Friend’s Ex?

Mean Girls is a classic for a reason. It captured the toxicity of the passive aggression that women often learn to give and receive, loads of memorable one-liners that never get old, and plenty of questions about the differences between being a girl’s girl and being a mean girl.

One particularly famous scene in the original movie is when Cady Heron (Lindsay Lohan) opens up about a crush she has on Aaron Samuels (Jonathan Bennett), a boy in her calculus class. The only problem? Aaron Samuels just so happens to be Cady’s new “friend” Regina George’s (Rachel McAdams) ex-boyfriend.

Her interest in Aaron is quickly met with wide eyes and Oh, no’s from Gretchen Wieners (Lacey Chabert) and Karen Smith (Amanda Seyfried), Regina’s minions. “You can’t like Aaron Samuels. That’s Regina’s ex-boyfriend…Ex-boyfriends are just off-limits to friends. I mean, that’s just, like, the rules of feminism. Don’t worry, I’ll never tell Regina what you said. It’ll be our little secret,” Gretchen says. Cady, though, doesn’t seem entirely on board and continues to secretly carry a torch for Aaron Samuels.

From that point on, the mere thought of ever dating one of your friend’s exes brought to mind that scene. Getting involved with a friend’s old flame goes completely against the rules of being a girl’s girl – even the mean girls knew that. And yet, you’ve found yourself in quite the predicament because you sort of have a thing for your friend’s ex-boyfriend. Well, actually, it’s more than just a thing. You have real, undeniable feelings for him. And you know you’re not supposed to, but you haven’t been able to convince yourself to not like him.

So, with this in mind, you can’t help but wonder: Is it always against the “rules of feminism” to date a friend’s ex, or is it more case by case? What if you’re missing out on the great love of your life because of this rule? Is there ever a time when it’s…okay? Justifiable? Or should you force yourself to just forget all about him? Here are a few questions to ask yourself.

How Serious Was Their Relationship?

Were they official, or did they just go on a couple of dates that never led anywhere? How long were they together? Were they ever serious about each other? Were they in love? How far did they go, physically speaking? The answer to any of these questions will alter whether it’s wise to pursue a relationship with him or not, but if there were ever a situation where it might not be a huge deal to date your friend’s ex, it would be if they weren’t serious or even officially together. If the extent of their dating was a few dates that didn’t end up leading anywhere, then there’s a chance that your friend won’t think too much of it.

But the things that will probably make it difficult to approach a relationship with him? If they were official, if their relationship lasted more than a couple of months, if one or both of them were ever serious about the other, and if their physical relationship ever went beyond kissing. Not only is it likely that your friend could feel awkward and betrayed by your new relationship with her ex, but there’s a good chance you could end up feeling jealous about the connection they used to share, even if it ended.

Has She Totally Moved On? Has He?

The longer a relationship lasts, the longer it takes for us to emotionally disentangle ourselves from it. And yet, there’s some truth to the old adage that time will heal at least most wounds. With this in mind, it’s important to consider whether or not your friend has totally moved on from her relationship with her ex or if her feelings are still raw.

Did they break up just a couple of months ago? Or has she since fallen in love with her new boyfriend or possibly even married someone else? The further away she is from her past relationship with him, the more likely it is that she won’t have quite as many objections to you dating him. On the other hand, if their relationship only ended last season, it wouldn’t be surprising if the thought of you going out with him would upset her – especially if she hasn’t dated at all since.

But let’s shift the focus away from your friend for a moment. What about him? Is he over her? Has he dated at all since their breakup? Is there any chance that he still has feelings for her? The last thing you want is to feel like a consolation prize, the second choice, the rebound he didn’t really want but went for anyway – or worse, the girl he only dated in order to make his ex jealous.

Are You Absolutely Sure He Likes You?

You know that you’re into him. You know that you get butterflies at the mere mention of his name, that your heart skips a beat whenever you see his name pop up on your Instagram likes, that if it weren’t for your friend’s relationship with him, you would’ve made your move a long time ago.

But do you know if he feels the same way? Are you certain that the feeling is mutual? Has he more or less directly expressed interest in you that clearly went beyond just a hookup or a “let’s just see where this goes” type of thing? Is there no doubt in your mind that he genuinely likes you? If you don’t have the assurance that he’s just as taken with you as you are with him, the risks may outweigh the benefits – and you just might walk away with a rejection and one less friend.

Is He Worth Losing Your Friend Over?

Here comes the most painful question of all: Is being with this guy really worth your friendship? Because the reality is, even if your friend has moved on and you’re sure he truly likes you, she still has every right not to be comfortable with the relationship – and there’s a chance that going forward with it could cost you her friendship. So, is he really worth risking your friendship for?

If you have very little doubt that he’s the one, or if you aren’t even that close with her, then maybe. But if what you feel for him could be a passing crush that would fade over time and with less proximity, or if she’s always been a good friend to you, we’d recommend thinking twice about diving into a relationship with her ex – and maybe even denying yourself the excitement of a new romance that could end just as quickly as it started, for the sake of your friendship. 

In the end, the question it all boils down to is this: Is your friendship with her valuable enough to you that you’d give up a potential relationship, or is your connection with him strong enough that it would all be worth it? Only you know your unique circumstances, so only you can answer this.

If You Decide To Date Him, Be Classy About It

You’ve gone through each and every question, and you’ve realized that you don’t want to pass up the opportunity to date him. And while you wish he and your friend had never dated at all, you’re willing to look past it. So, how can you start this relationship the right way? How do you navigate the waters of dating your friend’s ex in the classiest way possible, with the fewest feelings getting hurt?

First, be upfront and honest with your friend. Tell her about your feelings for her ex and ask for her thoughts. Be ready for a variety of reactions; maybe she’ll give you her blessing, or maybe she’ll get upset. Either way, make peace with the fact that your friendship, if it continues, will change. She might distance herself, refuse to hang out as a group, or pretend to be more neutral about it than she actually is. Let her decide the closeness of your friendship going forward. And once you start dating him, do your best to keep it low-key, even if that means not posting about each other on social media for a while.

Closing Thoughts

Every situation is different, but one thing is for sure – dating your friend’s ex can quickly complicate things. While it’s generally true that if it’s possible, it would be best to date basically any other guy, there are times when the connection can’t be denied and when you would regret letting the past dictate your future. Still, we advise that you really think things through before getting involved with your own Aaron Samuels.

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