Should You Date Your Friend's Exes and Old Conquests?

the cock block of the century
the cock block of the century

You're at the bar, with friends, when you notice the electricity in the air; you're having an intriguing conversation with someone who you want to take home and pound until the legs/wheel on your kitchen table/couch/race car bed give out. You can't help it, you're a sucker to chemistry and when two sexual people “lock-in” they generate a force of attraction that, like a 99 cent baby back rib deal at the local strip joint, is hard to resist. Ah, but there's a catch; this person that you want to pound like a raw piece of beef (or tempeh, if you're veg/vegan) used to date and mate with one of your close friends… What do you do about that?Well, children of the corn, I'm not so sure that there's an easy answer here. I can tell you that I've gone all the way with friends' exes and it's led to some awkward conversation, the dissolution of a friendship and some awesome sex, if not a rewarding relationship.

Cock Blocked and Two Smoking Barrels

However, I can speak to one particular situation where I was cock blocked before I could even get unzipped. Allow me to explain: Once upon a time I had a friend named Kayla. Kayla and I never really hung out too much, but when we did, we always laughed and had a good time and it was usually around my buddy, Mr. Riker. Now, I'm not going to bullshit you guys, I wanted to bend Kayla over a table and do things to her that are still banned in eight States in the Union. However, I kept it to myself and didn't “press the issue.” Fair enough. You see, Kayla and I would talk about getting together to grab dinner or drinks. Not really a big deal, it's what people do.

One day, I'd mentioned to Mr. Riker that I was attracted to Kayla. He got quiet and I asked him what was wrong. He said, “Look, brosef, I don't like my friends dating because if shit doesn't work out then I usually end up losing both friends and that sucks.” I looked at him and understood but I had to tell him that, while I understood his predicament, I had to ultimately dismiss it. I said, “Riker, it really has nothing to do with you. At all. We're two adults and YOU introduced us.” Our disagreement went on for a while longer after that; needless to say we didn't resolve that argument.

The following day I'd made plans to have dinner with Kayla, that night. When it came time to get ready, she texted me and told me that dinner was off and that she was sorry. After probing further, she had told me that she thought I was cool, but only as friends and didn't think our dinner was going to be about that… I continued to press and asked her why she said that. Enter Mr Riker. He had a conversation with Kayla and explained to her that my feelings were not precisely platonic. It didn't matter what I said, she still declined dinner…

I was pissed.

Did it end up being worth it?

I called up, Riker and let him know how pissed I was. He couldn't remove his own feelings from the situation and have two friends dating and potentially lose out on those friendships… Really, it, to me, was a practice in immaturity on his part. His meddling pretty much torpedoed that friendship. Had I gotten the chance to go out to dinner with Kayla, would anything have happened? Probably not and it's likely I would have picked up on the fact that she wasn't interested in me that way…

Should I have even bothered at all? I still think there was nothing wrong in trying and really, what did Riker expect? When you put two adults in a room and there's chemistry that develops you can't simply expect it to go away and have neither participant act on their chemically induced impulses. It doesn't work that way. Just is the way it is. If it's something that's going to bother you, don't put yourself in a situation where you have a front row seat to a train wreck you want no part of…

I'm still close friends with, Riker. I don't talk to Kayla anymore, though. I'm over it, though. In the end I suppose it doesn't matter; it just seemed needlessly dramatic and, really, no one wants that in their life.

What do you think? Should there be a hands-off policy for friends and your exes? Discuss in the comments below.

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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  1. Hmmm, I too, have had "intimate" relations with one of my friends exes, however, we (the friend and I) weren't all that close. I also have had my friends date my exes. I have a friend that has dated 3 of my ex-boyfriends and is actually married to one of them now. They have been married for 10 years at the end of this month.

    I will be honest, this particular ex-bf that she is married to was the guy I always thought I would marry, however, although our sexual chemistry was out of this world, we would have ended up in prison for killing each other had we stayed together…we fought constantly (we are both Scorpios). Anyway, I was upset when I learned that they were not only dating but living together. My friend tried to get in touch with me to let me know that they were
    seeing each other but at the time we were living in separate cities. I actually ended up finding out from my Mom. After the initial shock wore off and I had the opportunity to be around them, I have to say I was thankful that this amazing guy ended up with one of my best friends and not some ho! They have an amazing relationship, and to be honest, I even joked after he and I broke up that they should date, because they always got along better than he and I did. They both seemed grossed out by the suggestion because at the time they thought of each other as brother and sister.

    I am extremely thankful today that they are together, because you see my friend lost her Mom yesterday, and I'm so glad that she has such an amazing guy by her side to help her through such a difficult time.

    In hindsight, if it's over between you and someone, I think why not date someones ex? I mean yeah, there would be jokes about having one's leftovers, but leftovers aren't all that bad if they were a great main dish, right? 😉

    1. Hey Denise!
      Thanks for the thoughtful comment. I particularly love this phrase: "why not date some­ones ex? I mean yeah, there would be jokes about hav­ing one’s left­overs, but left­overs aren’t all that bad if they were a great main dish, right? "
      I completely agree!

      I think that there's a lot of selfishness involved when a person makes it taboo for their friends to date an ex… Sure, it would be awkard and even hurtful for a little while, but you're an adult. Get the f#ck over it and go about your own life and let others find happiness. Sharing is caring, after all. Ya dig.

      Thanks again.
      PS. I fixed your typographical faux pas, btw. 😉

  2. I'm not a fan of dating any friends' exes or dating within friend circles … it's just kinda awkward and makes things weird. I'm Indian but with a very very International background. I'm currently living in India and I managed to have a huge show-down with a very close girlfriend of mine just because her ex (he claims he was never her boyf) would 'speak' to me at parties with other people present. She thought I was going out of my way to somehow 'steal' him.

    People can be very insecure and for that reason alone – I stay as far away from friends' exes as possible. Sure when I was 13 – 16, I have had my friends ask if they can date an ex of mine but that's when you are a teenager and the whole 'girlf-boyf' is more or less hand holding, maybe kissing and that's it.

    A school friend of mine started dating this guy I broke up with when we were 13 – guess what – they got married last year .. they are still together 14 years later !!! Do I care – hell no. I think once you hit your 20's and your relationships take on more meaning – then it's difficult to digest when a friend wants to hook up with your ex.

    Unless I had deep feelings for someone to a point I wanted to spend my life with them – I don't quite care if a friend hooks up with my ex (mind you my friends don't have the same taste in men as me but I digress); if it was up to me to choose a random guy or a friends 'ex – I would go for the random guy. I don't need drama in my life !

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