16 Reasons to Not Date Your Friend’s Ex

He’s cute. He’s funny. He’s smart. He’s into you. Oh, and he’s your friend’s ex.

Yeah, honestly this article is only going to scratch the surface of why even entertaining this is all kinds of wrong.

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Now if the girl-friend is just someone you share a class or cubicle with, that’s not what we’re talking about here. What we’re about to tackle is when you have a really close friend who you spend time with and confide in (and they do the same with you) who has an ex-boyfriend who’d like to date you.

If that’s the case, we get why you might be tempted. But that’s not nearly a good enough reason to pursue anything beyond a hug when you run into him at the mall or the movies.

If you’re not totally convinced, here are some of the reasons why…

1. It’s not good for your friendship

16 Reasons to Not Date Your Friend's Ex
It’s not healthy for your friendship/via

If you and your friend are super close, then she probably told you about her relationship with the guy. Just think about how uncomfortable it will be for the both of you for her to know that not only are you aware of some of the innermost secrets of her relationship but now, you’re going to learn about some of those things firsthand. Yeah, awkward doesn’t even begin to cut it!

2. It could ultimately cost you your friendship

16 Reasons to Not Date Your Friend's Ex
It could ultimately cost you your friendship/via

If your friend does pretend that she’s cool with it at first (which is shocking all on its own), don’t be surprised if she’s not in the long run. She has every reason to think that you dating her ex is a bit on the side of disloyal. And when you don’t really trust someone, it’s hard to be friends with them.

3. It’s shady on your part (and his)

16 Reasons to Not Date Your Friend's Ex
It’s pretty shady on your part (and his)/via

Your friend is more than fair if she asks you how long you and her ex have entertained dating each other. And even if the topic didn’t come up before they ended their relationship, you certainly shouldn’t blame her for thinking that the two of you might have been sneaking around. And either way, thinking that being together is cool is pretty shady on both of your parts.

4. You’ll never be able to full trust him

16 Reasons to Not Date Your Friend's Ex
You’ll never be able to fully trust him/via

What would make you think that if he is OK with seeing two friends that he won’t mind doing it again with one of your other friends? And really, can you trust that? Probably not.

5. He might have a hidden agenda

16 Reasons to Not Date Your Friend's Ex
He might have a hidden agenda/via

Revenge reveals itself in a sorts of ways. And sometimes, you don’t really see it coming. Be careful about a guy who wants to date you shortly after his relationship ends with your friend. You might be nothing more than a pawn to hurt her feelings or make her jealous.

6. Chances are, you’ll dislike some of the same things she did

16 Reasons to Not Date Your Friend's Ex
Chances are, you’ll dislike some of the same things that she did/via

The reason why you and her are friends is because the two of you have some things in common, right? That’s probably why you like some of the same guys. Here’s what you probably weren’t prepared for, though. That’s also probably why you’ll end up disliking some of the same things about your friend’s ex as she did.

7. He may (openly) compare the two of you

16 Reasons to Not Date Your Friend's Ex
He may (openly) compare the two of you/via

It’s actually a given that he’s going to compare the two of you. That’s natural. What you might not be prepared for is him comparing you openly. “Sara would never wear that” or “Katie actually likes this restaurant, you don’t?” Who wants to feel like there’s constantly a measuring stick in their relationship. And not only that but someone who they actually know?

8. His friends may compare the two of you too

16 Reasons to Not Date Your Friend's Ex
His friends may compare the two of you too/via

Here’s an icky thought. Guys talk to their friends. This means that he talked to them about your friend (and who knows what was said) and now, you’re up for conversation. And yes, that also usually includes comparisons. Between you and your friend. This time, not only by one guy…but several.

9. It could be a reputation killer

16 Reasons to Not Date Your Friend's Ex
It could be a relationship killer/via

Honestly, at the end of the day, character should trump reputation. But in this case, they both basically work together. Even if you feel that dating an ex of your friend is the exception and not the rule, what is it about your character that thinks it’s a good thing to do? And if you don’t care, that attitude is what could ultimately affect your reputation.

10. You’ll both have messed with the same guy (Eww)

16 Reasons to Not Date Your Friend's Ex
You’ll both have messed with the same guy (Eww)/via

Doesn’t the picture basically say it all? Every time you kiss the guy, just remember that he kissed your friend. And how appealing is that? (No, we’ll wait for the answer on this one…)

11. You’ll have a hard time balancing the two relationships

16 Reasons to Not Date Your Friend's Ex
You’ll have a hard time balancing the two relationships/via

So, if you’re used to you and your friend telling each other everything and she can’t stand her ex and/or her ex can’t stand her either, how are you going to balance everything out? It sounds like a tug of war more than anything else. And what’s the fun/use/benefit in that?

12. It will be hard to get others’ support and understanding

16 Reasons to Not Date Your Friend's Ex
It will be hard to get other’s support and understanding/via

Hopefully, you have people in your life who are going to love you no matter what. But if a lot of them are like “We just don’t get this so we’re not sure we can offer the best advice”, don’t fault them for it. It’s complicated at best.

13. There’s a slim chance it will get anywhere…far

16 Reasons to Not Date Your Friend's Ex
There’s a slim chance it will get anywhere…far/via

When a guy knows that you’re willing to date your friend’s ex, it might cause him to wonder if you’re also capable of dating one of this friends up the road. That puts your integrity into question which may put an expiration date on your relationship before it even really gets off of the ground.

14. They might ultimately end up back together

16 Reasons to Not Date Your Friend's Ex
They might ultimately end up back together/via

Gee. Now wouldn’t this be a boomerang? How mad can you really be if after dating you, he goes back to the woman he was seeing before you? There’s a chance of this happening. Do you really wanna risk it?

15. There are plenty of other guys to choose from

16 Reasons to Not Date Your Friend's Ex
There are plenty of other guys to choose from/via

Aren’t there enough guys in the world that dating the ex of a friend is worth avoiding? Just asking.

16. You’re so much better than that

16 Reasons to Not Date Your Friend's Ex
You’re so much better than that/via

While there are rare instances where dating the friend of an ex could work, it’s close to the chances of winning the lottery. Between trying to get your friend to trust you, trying to keep the relationship from being super awkward and trying to keep any type of guilt at bay, you’re better than all of this. Don’t look at a close friend’s ex as “the ultimate catch”, but the ultimate distraction when it comes to finding someone who you—and your friend—can be happy about you being with instead.

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