Dating Your Friend's Ex. The Ultimate Smite, or a Prelude to "Hugging it Out?"

This post isn't really looking to offer any sort of advice really.  More or less I'm just unleashing some unsightly “thought vomit.”  You see, I've had this conversation before: Should you or shouldn't you date your friend's exes?  It's a good question.  Most people I've talked to have a pretty hardliner stance on the whole thing.  However, I've been on both ends of this powder keg of a discussion…
@singlecityguy of www.singlecityguy.com (great blog, by the way) offered this morsel of insight on the subject when answering my question:

“Well you need three kinds of clearance for that.  You need FAA clearance, several gun permits and plain old clearance and then your friend's clearance.  Oh and don't get me started on what it takes for Moms…”

All I can say is “just wow!'  That's a lot of damn clearance and a college semester's worth of studying up to get it all right, methinks.  However, my personal opinion is that there's nothing wrong with dating your friends' exes, even if they don't live in Texas (sorry, had to go for it!).  I've dated friend's exes and I've had friend's date mine.  Sure, there was plenty of awkwardness in each situation, but you get through it and if your friendships are strong enough you can work through the issues… usually.

There seems to be this prevailing bro-code that states “thou shalt not date a bro's ex.”  Simple and straight forward; but why?  Is it to avoid awkward moments?  Is it to avoid dealing with lingering feelings of hurt and/or resentment?  Respect?  It could be any number of things.  However, I think in a situation where there is a genuine bond between your ex and one of your friends the rule shouldn't apply.  That is, unless your ex isn't engaged in a plot to drive a dagger into your still-bleeding heart by sexing it up with your friends.

One of the first girlfriends I had, had dated and, I think, been engaged to a good friend of mine.  I didn't tell him about it right up front and that was wrong of me.  In fact, it took almost three years after the fact before I said anything.  In my defense, he would have used my head as a soccer ball.  Just sayin'.  That I told my friend that I dated his ex (I was no longer dating her at that point) was more a selfish move on my part as opposed to a “coming clean” session.  It opened a lot of old wounds and made things uncomfortable between my friend and I for a while… Was it worth it, dating my buddy's ex?  Well, in many ways, yes, it was.  I learned a lot from her (not in a sexual way, you pervs… though, it should be noted that I learned some there, too) while we were together.

I guess why I'm on board with saying “yeah, it's okay to date your friend's exes” because I feel that if adults are, in fact, adults they govern themselves and can make an intelligent decision.  That decision being to pursue the person that makes them happiest.  I would think that my friends would have my happiness in mind, regardless of who I date… Do I think there's a discussion that should happen before a decision is made?  Yes, I do.  I think it's the inherent responsibility of the interested party to approach their friend about the topic.  If it's really going to bother your friend and you risk ruining your friendship then make a judgement call and determine what is more important.  However, I feel that if a friend presents you with that choice it's pretty immature on the friend's part.

In yet another situation there was a person I used to be best friends with.  He and his girlfriend had broken up.  He asked me not to speak to her ever again.  At first, I went along with it going with the “bros before hos” mantra… That was dumb, though. This “ho,” so to speak, had also become a really good friend to me.  She had seen me go through a lot (and I mean A LOT) of issues, setbacks and heart ache. I grew to really trust her.  In thinking about it further, it became inconceivable to me that I could ever break that bond of friendship.  Eventually things with my “best friend” had soured and we had a falling out, one of those issues being my continued friendship with his ex girlfriend.  Now, my friend's ex and I never dated or did anything romantic together, we were friends only.  Oh don't go quoting me by saying “But, didn't you say that men and women can't be just friends??” Jerks. =)

On the other hand, I've been that guy that's had a friend date one of his exes.  The gal I had been dating at that time had broken things off with me and said “let's just be friends.”  It was difficult, but I was coping.  Since her and I hung out in the same group, we were always seeing each other.  I could see that her and a mutual friend of ours were “clicking” and hanging out a lot.  It bugged me, but I didn't say anything.  One day my friend approached me and we went out to shoot some hoops.  That's what manly men do when they want to talk about matters of the heart, ladies, do pay attention.

We played and we talked.  He told me how he felt about my ex and how much fun they had together.  I took it in and sucked it up.  I told my friend that I was fine with him dating my ex.  I told him that I'd probably be a bit of an ass at times about it, but that I would get over it and to give me time.  I even gave him pointers on dealing with my ex and things to watch out for.  Don't get me wrong, I still wanted to rip something limb from limb… but I knew that I'd be able to deal with it and that I was ultimately being very selfish.

At the end of the day that's what dating or maintain a relationship comes down to:  Maturity, respect and just being able to deal with one's feelings.  As with most things in life, it's a two way street.  The intent to date a friend's ex should be made known to your friend, whose “seconds you intend to plate on your own tray.”  Also a healthy look at oneself and what the friendship really means and what your friend's happiness means to you.

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  1. Its funny to me that people have those hard-fast rules of "If I dated her, you can't". In some cases, I get it. I mean if there is a huge pain thing there and your friend isn't over it yet, its probably best to leave that ex alone.

    Otherwise, with some time after they've broken up and moved on, I don't see the issue.. provided that you ask/notify them before going public with it… and that the point of it is not to hurt anyone, but merely that you really do think that being with that person is going to make you happy/happier.

    Actually if a friend of mine wanted to date my ex-husband, I'd be more than happy for them both, and give her all sorts of advice about how to make it work.. of course after a very long conversation of "Seriously? Are you on crack?" but hey if she convinced me that she'd be happy with him.. why not?

    Stealing them while you're still with them though… No.. a friend doesn't get forgiven for that.

  2. Can I give you a non creepy hug? 😉

    I think you further my opinion on this topic. It comes down to maturity, ultimately. Oh and stealing someone's cookies that don't belong to them is a big no no. A big no no.

  3. I think it's a complete case by case situation. I would most likely be fine with any of my friends dating my exes if things ended in a friendly manner. Sometimes it doesn't work out, if you're friend and your ex are better suited why stand in their way? In fact I've set friends up with some of the guys I dated before. It's about letting go of the feelings and being an adult about it.

    However. I can't understand a friend of mine asking permission to date a man who treated me poorly. That would be absurd.

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