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When Should You Go After Your Friend's Ex?

should you date your friend's ex
should you date your friend's ex

You've probably heard about this before, from a trusted friend: “Hey, I got someone I want you to meet. Oh yeah, she's pretty hot, good appetite for the sex and stuff. How do I know her? Oh, I, uh, used to do her; I mean, um, she used to be my girlfriend. But, um, we're not dating anymore… So, yeah, wanna hit it?” Okay, that's not likely what you have seen before, but you know what I'm getting at. Would you pawn an ex off on one of your friends? Is it a good idea? How long should you wait?My girlfriend and I are not talking right now, because she is wrong… At least that is what I told her before she stopped talking to me; something tells me that I am wrong, but my male DNA refuses to admit it. “Keep reading your Newsweek honey.”

Anyway, the topic of picking up your exes leftovers is always a hot-button topic. Should you or shouldn't you? I'm probably not the right person to ask, since I do keep in contact with some of my exes and have tried to set them up with my friends…

Some question the wisdom of doing that. “Dude, don't you think that's just weird?” some will ask. No! I don't think it's weird at all. I'm a connector, dammit; I bring people together, or at least I think I do. I try to match up people when I can, I love seeing people happy. Sure, I get a bit of an ego boost when I help make a match happen; but who wouldn't?

That said, I do think it's okay to make a move on the ex lover… However, you shouldn't do it without fair warning or discussion with your friend first. Just to add some color to the convo, here's what some Twitter-philes have said:

[blackbirdpie id=”58218925250457600″]

[blackbirdpie id=”58210049755054080″]

[blackbirdpie id=”58226138065022976″]

[blackbirdpie id=”58225305176911872″]

I stand alone in the leftovers discussion. You are a giant turd. I win!

As evidenced above, not a lot of people feel that hooking up with a friend's ex is a good idea, let alone agreeing to the best time to hookup with said ex. In keeping with the question, “when is the right time to hookup with a friend's ex” it doesn't require a lot of thought, really. Just stick with me for a moment; hear me out.

Once upon a time  I was dumped by a girl who I was convinced had halitosis… She was a big part of my social circle and we shared many of the same friends, so I would see “Dragon Breath” (what I affectionately referred to her as) often, too often. It was a miserable time for our idiot… er… hero. However, my heart kept a beat for her… Yet, that heart did not beat alone. No, there was another.

A great disturbance in the force… not in my pants

The “other,” I mentioned, was my good friend, Ian. Ian had developed a like for Dragon Breath and I knew it. I could see the smitten look across his face. I could have drop kicked him or sucker punched him in the urethra; it was made worse when I watched Dragon Breath and Ian flirt… I couldn't take it. One day Ian shows up to see if I want to play basketball… We NEVER play basketball.

So there we were on the court, shooting around for what seemed like an eternity, like ten minutes, when I grabbed the ball and held it, much the same way a terrified mother holds her baby close to her breast. I sniffled and asked, “So, Ian, what the fuck are we doing here?” Ian followed up with, “So you and Dragon Breath… What's going on with you two?” At this point, I knew where this was going… I stood there, silent, clutching the basketball (or the rock, as we are known to call it) tightly to my man tits, I looked down and whimpered, “You wanna date Dragon Breath, don't you?” Ian shook his miserable James Edward Olmos pock-marked face and said “Yeah, man, I'd like to take it to her and break her hymen all over again…” Okay, okay, that didn't get said, but that's how I processed it mentally. However, I told Ian that it was okay and that I would deal with it.

So I did. It took a while, but I got over it and found an older pair of boobs to drown my sorrows in…

Is it okay to partake of your friend's leftovers?  I think so. It ain't easy though, don't kid yourself. When should you go for it? After you ask your friend and they tell you “it's okay.” Otherwise, get off the pot already.

Author profile

Alex is the founder and managing editor at the Urban Dater. Alex also runs: DigiSavvy, for which he is the co-founder and Principal. Alex has a lot on his mind. Will he ever get it right? If he does, he'll be sure to write.

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7 Comments

  1. I'm going to be real sexist right now. You say this because you're a man. Somehow you harder types can get over things easier, faster…or at least you act like you do. Us ladies, nu-uh. My girlfriends would kick my girly *ss if I attempted to date any one of their exes. I'm not going there, I like my booty just the way it is!

    1. Oooh, I like sexist women. It's so… sexy! =)
      I don't know that it really has much to do with being a guy though. It took me a long while to get over that girl, which wasn't helped by her being around as often as she was and hanging over the new guy, who was a friend of mine. Trust me, man or woman, there's plenty of ass kicking to dole out.

      I guess it comes down to how much BS you're willing to put up with.

  2. Its really tough to date the ex of your friend.I can't go with it.To find a new is better than dating friends Ex.Its my personal view but people have different views about this matter.

    1. Sure, there are different view points… I often look back and wonder why I put up with it. I tell myself that it's my good friend and I want the guy to be happy. Even though things ended badly with my ex, I didn't wish her ill. Perhaps I'm just cheesing out here, but I really did expect that they could find happiness, which would have made me happy, even if a bit uncomfortable.
      My recent post How to Publish Your Content Everywhere

  3. You don't own an ex. What is this? Slavery? You might not like it if a friend dates an ex, but get over yourself already. They're an ex for a reason: you're a douchebag. You don't get to control anyone's life. You're not Zeus, FFS.

  4. All is fair in love and war. If you're done with them then why stand in the way of your friend who may be happy with your ex? I set my exes up with my friends. I even set Alex up with my friend! People need to stop being so possessive, if your ex & someone else you know are better matched, wish them the best & go meet someone who wants to be with you.
    My recent post California Love

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