Ask Him: Can I Pursue My Friend’s Ex-Boyfriend?

Q:  “I’ve been attracted to my friend’s boyfriend for a long time. They just broke up. Am I allowed to pursue him? And if so, how long do I have to wait, or what do I have to do to make sure my friend is OK with it?”

dating friend's ex

discretion is key.

A: Yikes, ma’am. You’re on some serious Simon Cowell sh*t right now.

My knee-jerk reaction to this question when I first read it was that you should absolutely NOT EVER pursue your friend’s ex-lover. But like any question you would decide to submit to a guy who tries to give advice to women, the answer is not as easy as your knee-jerk reaction.

Also, I’ve hooked up with a friend’s ex before.

I’m most definitely not saying that this is a good idea because most of the time it’s not, but I feel like I should be honest with you and let you know that I’ve done this before. (And in my defense, my friend was married to somebody else, but more on that later.)

Like most difficult life choices, this is a nuanced thing that depends on a number of variables. When discussing this with my dear editor and friend Arianna Schioldager, she told me that pursuing another girl’s ex is ostensibly a violation of Girl Code.

“It also depends on who broke up with whom,” she added.* “Like if he dumped her, NO WAY. If she dumped him, she probably doesn’t want to hang out with him anymore.”

So there’s that. If he dropped your girl like last week’s beat, not only should you not pursue him, but you should decline any advances he might initiate. What I’m saying is you can’t hit that. At all.

Unless you don’t care about the swift and complete ruination of your friendship. Which I don’t think is the case, because you wrote to me instead of immediately going out there and trying to bang your friend’s ex-boyfriend.

Now, if your friend broke up with him, then your road to becoming her Eskimo Sister** might be a little less paved with horribleness. Like Arianna said, she probably doesn’t want to be with him anymore. But you still have to have a serious talk with her before you make even the slightest move. I’ve noticed that even after people have allegedly completely moved on (and are even in serious relationships with someone else), they still feel slighted or weird or put off by your interest in sampling a person where they first planted their romantic flag.

And I should add that before you have this talk with your friend, you should analyze the situation that led to her decision to break things off. As a friend, you’re likely already privy to this information, but you need to make sure that there isn’t something about him that made her call things off that could also affect you. Like, maybe she declined to mention that her boyfriend had a weird collection of Barbie and Ken dolls that he likes to put into compromising positions or something, but she’ll definitely make with such insider information when you approach her about trying to bat cleanup on her previous man.

At the end of all of this, you should consider if this dude seems really worth all the baggage that will inevitably come with trying to date him when he has already been with your friend. (Friendly group hangs will surely be awkward.) There are plenty of other guys out there, and don’t fool yourself by trying to convince yourself that fate is urging you to go for this one person. Because fate doesn’t exist for people who aren’t trying to justify something that they can’t otherwise tangibly and/or rationally explain.

If after a while you still find yourself holding a flame for this bloke, then that is what it is. But if you can, wait until your friend marries someone else. Because then she can’t justifiably object to you going after someone from her past.

Good luck!

**This is the title for when you have had sex with the same person as someone else. It’s also known for dudes as “Tunnel Buddies” but I don’t think that applies to women. For obvious reasons.

Image Credit: Deviantart/audrenlerioual

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