Would you ever date your friends ex-girlfriend (of two years)?

Never okay. This recently happened to a couple of my friends who lived together for a year. During that year, friend "A" dated a a girl for 9 months. They broke up shortly after the two friends stopped living together. Friend "B" started "hanging out" with the girl a bunch and asked friend "A" if it was alright if he started seeing her. To not make things awkward, he said it was okay but he meant in no way that it was alright for him to do it.

We all just look down on this friend B now...especially when he brings her around. It's just weird and he should have known better.
 
Well, in that case Friend A should have just been honest and said that he wasn't ok with it.

But it is a good example of how it makes things awkward in social circles, and why I try to stay away from it. Good friendships are hard to find, and relationships are hard enough, without added problems like that getting in the way.
 
Don't do it. Even if your friend is a man about it and wouldn't stand in your way and says all the right things, he's bound to be affected by it more deeply than you might think and for much longer than you might think. Don't underestimate the severity of private suffering on his part. If your friendship means anything at all, you'll forever shut the idea of dating his ex. There are, after all, times when noble character means abstaining from base desire. There are plenty of fish in the sea anyway.
 
It's probably better to find someone else but, that said...

If you're really into this girl (are you, even?) I think there is a way you can approach this without being a piece of sh!t:

Ask him. Do it very, very gently and make sure to impress that if he would not be ok with the idea, in any way, that you absolutely would not (and WILL NOT ) if he says no. In that conversation I would emphasize your friendship with him above all else and that you are trying to be honest and open and will absolutely respect his wishes.

This is the kind of conversation that you have before something happens with the girl.

The advice people are giving to wait two years.. come on - that's not realistic. If you really like her that much, it's a far too long and unrealistic time-frame to pine over someone. I think you're setting yourself up for some "whoops we had some beers and hooked up," if you're keeping this two-year time frame in the back of your head.

I had a similar situation where I dated a girl that one of my best friends had dated for a while (far shorter than two years (he broke it off with her, for the record)) but we managed to work it out. It wasn't completely smooth sailing - I won't lie to you there, but we talked about it and I don't think he felt like he was burned or backstabbed. A year later, I'm not with the girl, but him and I are still super good friends.
 
[quote name='Dingleberry']To not make things awkward, he said it was okay but he meant in no way that it was alright for him to do it.

We all just look down on this friend B now...especially when he brings her around. It's just weird and he should have known better.[/QUOTE]

That's the dumbest thing I've ever heard. To make things not awkward, Friend A said the complete opposite of what he felt. And now it's awkward all the time when friend B comes around?

Friend A is a moron.
 
[quote name='Eviltude']If you can bring yourself to stick your meat where your friend had his for the last two years, go for it.[/QUOTE]

I would not be able to stop thinking of this if I was in such a position.
 
[quote name='coltyhuxx']Ask him. Do it very, very gently and make sure to impress that if he would not be ok with the idea, in any way, that you absolutely would not (and WILL NOT ) if he says no. In that conversation I would emphasize your friendship with him above all else and that you are trying to be honest and open and will absolutely respect his wishes.[/QUOTE]

Pointless. See:

[quote name='Dingleberry']Never okay. This recently happened to a couple of my friends who lived together for a year. During that year, friend "A" dated a a girl for 9 months. They broke up shortly after the two friends stopped living together. Friend "B" started "hanging out" with the girl a bunch and asked friend "A" if it was alright if he started seeing her. To not make things awkward, he said it was okay but he meant in no way that it was alright for him to do it.

We all just look down on this friend B now...especially when he brings her around. It's just weird and he should have known better.[/QUOTE]
If you ask the guy, he's just going to lie and say he's OK with it, and then treat you like shit for the rest of your life for believing him.
 
[quote name='pete5883']Pointless. See:


If you ask the guy, he's just going to lie and say he's OK with it, and then treat you like shit for the rest of your life for believing him.[/QUOTE]

Then that is his problem and he isn't such a good friend himself if he can't be honest with you. I am not for or against it myself either way, it really depends on a lot of circumstances to me. Personally I wouldn't want to be friends with Dingleberry, his group of friends, or friend A in their case if they were going to look down on friend B over friend A's mistake.

I can almost promise had friend A told friend B that he was uncomfortable with it and been honest the way friend B was by coming to him, friend B would have backed off and wouldn't have held a grudge. In my eyes, friend B is by far the better friend even if he is the one that ended up with the girl because he didn't bullshit around with the situation.
 
I don't see a big problem with it (hell, technically, my mom married her sister's ex, and they get along fine.) Just be slow about it- don't go hopping into bed with her 2 weeks after the breakup if they do. And asking is fine- considering he's brought it up before, and his girlfriend has brought up being into you before, I think if he has half a brain he should know it's a serious question demanding an honest answer.

Just take your time with all of it... after they break up. I mean, they could work things out and this'll never be an issue, too.
 
[quote name='jaykrue']Why would that matter? :whistle2:s Every girl that has become sexually active has at least had one cock in the vicinity of her mouth not to mention the facial from the resulting orgasm. How is having a stranger's cock different from your buddies' aside from knowing the latter in person? As long as the girl doesn't have a dick in her mouth or jizz in her face WHILE you're kissing her as well as keeps herself generally clean, I don't see how this warrants serious thought (unless you're into that stuff).[/QUOTE]

You need to lay off the porn my friend.
 
What's going to happen if this chick starts banging some other random dude? Your buddy is going to be depressed, and you'll have missed out.

I don't know what I'm saying. I guess you'll make up your own mind, becuase I can't seem to.
 
Make sure your friend truly doesn't have any lingering feelings for her after they break up and is over it before you do it. Wait too long though and she'll just find another guy. You just want to make sure it won't be miserable for your friend if you all every hang out again.
 
[quote name='bvharris']You need to lay off the porn my friend.[/QUOTE]

And you need to grow a few pube hairs before you speak.
 
[quote name='bvharris']You need to lay off the porn my friend.[/QUOTE]

[quote name='jaykrue']And you need to grow a few pube hairs before you speak.[/QUOTE]

Oh, this won't end well at all.
 
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