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Let’s get this out of the way first because we’re all thinking it: you probably shouldn’t date your friend’s ex. If at all possible, avoid dating your friend’s ex. It’s sort of one of those unspoken life rules. But then again, there are exceptions to every rule. You may find yourself in the rare situation where your friend is truly over her ex (or says she is), gives you full permission to date her ex, and knows that you and her ex are actually a great match. So let’s say nobody’s feelings are hurt on either end of things, and you know that your friend’s ex is the man you’re meant to be with—things are still bound to be a little weird. Nobody can help that! Here is what it’s really like to date your friend’s ex.

A troubled wife turns to Reddit for advice after struggling to forge a relationship with her new husband's ex.


She can relate to the fights

When you complain to your friend about annoying things your partner does or the fights you have, she can totally relate. She used to date him! She completely understands your frustration, which is at once comforting and strange. It almost feels especially wrong to vent about your boyfriend to your friend when they used to date. She certainly doesn’t have an objective opinion.




He can feel teamed up on

Your boyfriend will feel teamed up on anytime you and your friend disagrees with him. In fact, it will probably always make him a little worried if and when you run to your friend during a fight with him. Even if they’re on good terms, ultimately, your friend deemed him not a suitable partner. It’s hard for your boyfriend to believe your friend (his ex) isn’t whispering some bad words about him in your ear.




You’re Eskimo sisters…

You’ve had sex with the same guy. That’s weird. There’s no way that isn’t weird. He has received oral from both of you, and can compare and contrast. Damnit—he better not be comparing and contrasting!






You’ll swap vacation stories

When you and your boyfriend come back from a trip to Las Vegas, you’ll tell your friend all about it. And then she will tell you about the time she went to Vegas with your now boyfriend when he was her boyfriend. You’ll all swap stories about the restaurants you visited and the shows you saw. It will all be a little too Freaky Friday.




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His parents already know you

When your boyfriend brings you home to hang out with his family, they’ll do a double take. “Wait a minute…we’ve met this woman before. Wasn’t she at your ex girlfriend’s birthday party? And at your last house party? Oooooh….” Hey, at least they’re already familiar with you.





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Her parents are a bit confused

If you’re close with your friend’s parents, then you likely bring your boyfriends around them. That means when your friend invites you and your boyfriend to Christmas dinner at her family’s house, you’re bringing her ex. That’s a bit uncomfortable for everybody. This is the same ex that your friend was once crying about to her family after a breakup. Now, he’s eating their Christmas ham.




Some friends stop trusting you

Some friends will label you a boyfriend stealer and wonder if you’re sizing up their men as potential future partners. There’s little you can do about that but stick with your boyfriend and show the world you chose him because he’s the one for you and no other reason.





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People always ask her if she’s okay

People will probably ask your friend, “Are you really okay with your friend dating your ex?” every time you’re all together in a social situation. Some friends will even become detectives, looking for clues your friend is actually not okay with this. It can be very hard for many people to accept that this is a pain-free situation.





Your friend and your man may still fight

Your friend and your boyfriend broke up for a reason. On some level, they didn’t get along, didn’t see eye-to-eye, and just didn’t mesh. Those dynamics may come out again, and if you ask for all of you to spend time together, they may bicker. In other words, your best friend may not like your boyfriend very much.




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Her new bf and her ex have to hang out

Since you are keeping your friend’s ex in her life by dating him, that means any guy your friend dates will now have to meet her ex, too. No matter how you do the math, there will be two exes sitting at the table when you all go on double dates. That can be a lot to handle for the men your friend goes out with and, the truth is, you did that to her.



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You know all about their sex life

Because she used to tell you about it! Hey, how was your friend supposed to know, back in the day, when she was hot and heavy with her now-ex that he would someday be your boyfriend? She didn’t. So she told you every nasty thing they did in bed together. It’s hard for you to get rid of those visuals.






You work hard to make things different

You have to work hard to make sure you and your man don’t fall into the same routines that your friend and your man used to. If you guys end up eating at the same restaurant every Friday and visiting the same dog park every Sunday that they used to, that feels a bit bizarre.






You keep an eye out for old patterns

You’re well aware of the mistakes your man can make in a relationship. Remember that your friend used to tell you all about it. If you see even a hint of those old patterns popping up in his behavior, you panic.






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She still has his gifts

When you go over to your friend’s place, you drink out of the mug your boyfriend gave her, borrow the slippers he left there, and even see some of the old, romantic birthday cards he gave her.







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In ten years, nobody will care

The good news is that, while this may feel challenging now, in a decade, nobody will remember. Everybody will be busy with their spouses and their children and no one will remember how anybody got coupled up and settled down.

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