Nine Reasons You Shouldn’t Date Your Friend’s Ex

14 Min Read

When it comes to dating your friend’s ex, most of us know “The Code.”  It’s that Girl Code that contains the unspoken rule that dating your friend’s ex is TOTALLY out of the question. He’s off limits…period. But are there any “loopholes” when it comes to this “rule?” For example, what if they dated in high school and you’re now 40 years old and your best friend is married to another amazing guy? What then? Is it okay to go after a friend’s ex after a certain amount of time has passed?

Dating is hard, and when there are slim pickin’s, it’s not easy to just toss a good guy aside. If there is a genuine interest, a real chemistry and a feeling deep in your heart telling you that he might be The One, are you supposed to ignore that because of the “Code?” Or…do you follow your heart,friendship be damned? It’s tricky, but not unheard of. If you have your sights set on your friend’s ex, consider these things before you break the “Code.”

 

1. WHY DO YOU WANT TO DATE HIM?

It could be that you crossed paths with her ex, had no idea who he was, and the stars aligned so that you two could be together. But if she’s a long-time friend of yours, chances are you know all about her men, old and new. However, if she’s a “new” friend of yours, a colleague at work or social acquaintance, you may feel that the bond between you and your “friend” is not as strong and therefore, he’s fair game. Either way, examine your motives for even considering dating a friend’s ex. Are you secretly jealous of her and want to take what she has? Do you two have a healthy – or not so healthy – competition with each other and dating her ex is a way to “win”? If you want to date him for reasons that really have nothing to do with him, and more to do with causing her hurt, anger or embarrassment, you’re not a real friend and karma will be a b–ch!
2. IS HE WORTH THE DRAMA?

It’s one thing to find someone sexually attractive and to lust after him – hey, it happens – but totally different to feel a deep connection and think that he’s your soul mate. After all, you may have had time to get to know him if he’s in your circle, and now you feel the Universe is telling you that he should be your man. But take some time to really think this through. Is he a really good guy and things just didn’t work out for them, or did he treat your friend badly and you just hope he doesn’t do the same to you? Is there really something about him that you haven’t been able to find in any other guy that you’ve dated? What makes him so special? Answer yourself honestly and really determine if pursuing a relationship with this guy will be worth all the drama that could possibly ensue. If he’s “one of a kind” and you can’t see yourself with any one else but him, you have to proceed with caution knowing that your heart simply wants what it wants.
3. DOES HE FEEL THE SAME WAY?

If you’re going to possibly ruin a friendship, not only do you want to make sure he’s worth it, but you want to make sure the feelings are mutual between you two as well. Has he been flirting with you the entire time he was dating your friend behind her back? If so, you may feel that it’s really YOU that he wanted all this time, which can be flattering if you find him attractive as well. But, be careful because he could just be a jerk who looks to bag his girlfriend’s friends because he sees it as a challenge. If that is the case, not only is he grimy, but he’ll do the same thing to you. But if he’s an ex of hers from a million years ago, they ended on good terms and you are relatively new to him outside of their past relationship, then chances are he could truly be into you. Just make sure you know for sure before you let the world – including your friend -know that you and her ex are planning on kickin’ it.

4. BE DISCREET?

Sometimes, the only way you’ll really know if the relationship is worth causing drama is if you start dating the ex-boyfriend secretly to see if there’s really something there. I know this sounds shady, and it probably is, but this way you can determine if this is a relationship that has real potential or if it’s one that will crash and burn so quickly no one will even notice. Start hanging out with him and tell him that you want to be discreet for a while before considering telling your friend or going public. I know it sounds like sneaking around (it is), but the last thing you want to do is tell your friend that you want to date her ex, ruin the friendship and then the relationship doesn’t even work out. Then you will have lost a friend and a guy? Know what’s worse? You’ll probably miss your relationship with her more than the potential one you had with him. If it doesn’t work out between you two, there’s a possibility you don’t have to tell your friend at all. But if things go well, then you’ll have to decide how and when you tell your friend that you’ve been dating her ex behind her back. Hopefully by then you’ll know that he’s worth it.

 

5. IS YOUR FRIENDSHIP STRONG ENOUGH?

You may have decided that your friend’s ex, your new man, is the one you’re meant to be with ad that’s fine.  But have you stopped to think if your friendship is strong enough to handle what she could see as a betrayal? Now, if you two have talked about boundaries or if exes are off limits and she has said that she couldn’t care less, then you probably already know that your girl won’t have a problem with it. After all, she didn’t want him, and she wants you to be happy –which is a very mature way to look at it. But if this is something you two have never discussed or she just assumes that all women know the “Code,” then you have to determine if she’s a friend that you want to risk losing her forever. Like I said before, if she’s just an acquaintance and there will be no love lost, go for yours. But if she’s a dear friend who you don’t want to hurt, really ask yourself if the friendship you think you have is strong enough to get through this.

 

6. TEST THE WATERS

Okay, so you’re not sure if you have the type of friendship that can sustain anything; you don’t want to lose her friendship but you’re also not sure you’re willing to give HIM up either. Rather than sneaking around with him, why not test the waters with her first to gauge her feelings on the subject? For example, say something like “I know you and John haven’t dated in eons, and you two are (not) still cool, but would you have a problem if he and and one of your friends started dating?” Or you could simply ask her how she feels about her friends dating an ex of hers. If she says she’s cool with it, read her body language to determine if she really means it or if she’s just saying that to appear “evolved” or “mature.” Most men and women, no matter how “cool” they try to be, would have a real problem with this whether they want to admit it or not. However, if she says she would never approve and would cut a chick who even thought about dating her ex, then you have your answer and you can decide how you want to proceed from there.  Some women may qualify their answer, saying it depends on which ex, how long ago they dated, how serious it was, etc. If the ex that you have your eyes on falls into the “it wasn’t that serious, you can have him” category, then tell her then and there that you sense an interest between you two. But if he was one of the biggest heartbreaks of her life, then stay away from him.

7. CONSIDER ASKING FOR PERMISSION

So say your friend says she couldn’t give a rat’s behind who her exes date – including friends – and she appears to be totally cool with whole idea, I still think it’s in good taste to actually ask your friend for her blessing in dating her ex. It’s only right and she may appreciate you more as a friend for having the courtesy and decency to tell her and ask for permission. You may think you don’t need to ask permission because you’re a grown woman or because you’re afraid she’ll say no. But if she’s a good friend, asking for permission is the respectful thing to do. After all, you’d want the same consideration.

 

8. WHAT IF PERMISSION ISN’T GRANTED?

If she says no and curses you out for even thinking that dating her ex is okay, then you might have done irreparable damage to your friendship already. But if you’ve been friends for years, she might simply say “no” and keep it moving…and then keep all her boyfriends away from you on the sly until she determines that you’re not a sneaky witch. But if you ask, make sure you’re prepared to let the guy go – don’t just ask simply to do it only to date the guy anyway. Be sincere when requesting permission and take the answer she gives you to heart. If you plan on dating him regardless of her answer, don’t even bother asking.

9. WHAT ABOUT YOUR “CIRCLE?”

Even if your girlfriend gives you permission to date her ex, your other mutual friends may not be as understanding. They may give you the side eye and label you a man-stealing, backstabbing wench – and will probably make sure that you are NEVER alone with any of their boyfriends. If this is the case, you may have to do some damage control before you ease him (back) into the circle and go public with your relationship. Not everyone will be cool with it, especially if they feel you have ulterior motives or always wanted him behind your friend’s back. Be prepared to take the backlash that will be coming your way and make sure your man is willing to take the heat with you.  It may take them some time to see that you and her ex really DO have a connection and make a great couple, so just weather the storm or stay away from the naysayers for a while until everyone is on board. Like I said before, hopefully you made sure that he’s worth all this drama, because a real friend would never break “The Code” unless he’s really, truly The One.

 

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