Is It Ever Okay To Date A Friend's Ex?

Have you ever had a moment when you met someone utterly amazing? The time you spent talking with them made you yearn to close the distance between you. It’s truly an incredible feeling and when you discover she’s single, there’s nothing you wouldn’t do make a date with her happen.  That’s until you learn something you didn’t want to hear… that she’s the ex of one of your closest friends.

This isn’t a clear case of ‘ignore your feelings and cast her aside because there are plenty other women to go after’? No, it’s not that easy because the connection was a strong one. And everyone knows the strong pulls of the heart (or the loins) can’t be easily ignored. I’ve decided to write about dating your friend’s ex because I’m watching one of my friends wrestle with this problem right now.  Here’s the questions I posed to him to help him figure out if he should forget the girl or go ahead and have a talk with his pal so he can make this date happen.

Is there a Bro Code between you and your friends?
Guys live by a code that women don’t completely understand.  And I don’t care how many degrees in Psychology women may have, or how many brothers we may have grown up with, only another man can understanding the interworking of the male psyche.  All women can do is guess, assume, or hope they’re right.  So as you can see it’s pretty much hit or miss. 

What we know is a group of close guys friends have an unspoken rules about women they call their girlfriends, fiancés, or wives.  Women understand that men usually they don’t flirt with each others’ women, ask for graphic sexual details about someone they consider ‘wife material’, or stare at someone’s women for longer than absolutely necessary. 

But when it comes to ex-girlfriends. ex-fiances, or ex-wives, it gets a little tricky but one thing all guys seem to agree on is no man should to start a relationship with their friend’s ex unless he has done his due diligence first.  The phase, “Hey, man I didn’t know,” won’t wash between buddies. So if you’re thinking about touching any part of your friend’s ex’s body, you better know chapter and verse of your ‘Bro Code’ rules before you do.

How serious was the past relationship?
If the woman you’re interested in was once your friend’s high school sweetheart, long-term girlfriend, fiancé, or wife, you’ll need your friend’s blessing before you even talk to her.  Yes, that’s right; the beauty shouldn’t even know you’re thinking about her without your boy’s approval.

Now this isn’t a conversation you can have over the phone or via text message because you need to see your pal’s honest reaction. Some guys are very in touch with their emotions of shock and anger so they’ll let you know right away if they aren’t pleased with your request.  Other men are a bit detached from their emotions, so they could say they don’t have a problem, then display a very bad attribute for the next couple days. And there are some guys that are genuinely okay with you dating their ex because they are happy with their current relationship and have no intentions of going back to their ex.

But no matter what kind of response you get after you talk to your friend wait two weeks before contacting the woman in question. Why two weeks?  Well, because you have to make sure your friendship survived revealing your attraction towards your friend’s ex.

Some men may start speculating about your previous contact with women they’ve dated and may doubt if you’re capable of respecting relationship boundaries. So take my word for it, give your friend time to adjust to the idea before you try to talk to his ex.    

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How long ago was the relationship?
If the romance in question only lasted the duration of your junior prom and everyone is now over the age of twenty-six then you’re completely safe. If the former couple broke up last week and your friend currently trying to get his stuff out of her apartment, don’t be a moron and ask if you can date his ex. Such an ill-timed conversation is hilarious on a sitcom but could get your nose broken in real life.

Even if you know your friend was a lousy boyfriend to a great woman, you have to have some empathy for his feelings and wait for both parties to have the closure they need. This may mean waiting for both of them to have some transitional relationships and/or being able to hear each other’s name without looking like they smell raw sewage. This healing process may take months or even years so if the woman isn’t worth that kind of a wait then do everyone a favor and move on to liking someone else.

Is she the one, or just a woman you want to sleep with?
There’s a big difference in wanting to settle down with one woman and wanting to experience a woman in bed for a season or two. Make sure your head, the one with the two ears attached, is the body part making the decision to pursue this woman so vigorously. Choosing your friend’s ex can’t be about competition or trying to live out some forbidden fantasy, if she’s not the one you could see yourself with for a long time, save yourself any damage to your male friendships.

If this woman seems to get along well with everyone in your group, there’s nothing major you want to change about her, you adore her personality, and the thought of having a long relationship doesn’t scare you at all. Then she may be worth talking to your friend and asking if he’s over losing such an obviously wonderful woman. Just remember if he looks at you like he’s going to tear off your arms, he’s not over the breakup.  

Will any relationship with her put a strain on your friendship with your boys?
Let’s say your friend is totally comfortable with you dating his ex. That doesn’t mean the rest of your friends will automatically like the fact that you are dating (blank’s) ex.  You’ll need to do damage control before you ever bring this lady to a group gathering. Your decision to date her will be an unpleasant topic for some, and accusations that you always wanted to ‘steal’ her away from your friend may be implied by your group of buddies, but you’ll have to weather the storm and be honest about your thoughts and feelings.

Remember a strong man can take little retorts and snide comments from his pals. If you really like this woman then it will take some time for them to know if it’s a good match.  Don’t expect them to come around a few days after they learn the news.  If they’re good friends they’ll want to make sure this lady’s ex is totally okay with this new dating arrangement.  They’ll also expect you to prove you’re still the same loyal, reliable, and honest friend they knew before you decided to pursue this beauty.

Let your gut and your brain guide you on how to maintain your bond with your boys while dating this woman but make no mistake about it, she better be ‘The One’ because only a real jerk will dating one of his pals exs just to get laid. That's all for now, guys.

Stay confident, handsome and otherworldly! 

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