I know a guy. Let's call him Tom. He's a best friend, and the only person I know with whom I can carry an intelligent conversation with that neither makes me like an idiot or a smug asshole (then again, I don't have a lot of friends). We've known each other for a few years; he was with me on my 21st birthday to get hammered drunk with the family (as is tradition), and I was there for his a few years later.

All the time I knew him, he had a girlfriend. Let's call her Lynne. She was cute (I'd say a good 7-8/10), as well as being well-read and could carry a conversation, which I find huge turn-ons. When Tom, Lynne and I would hang out with other guy friends, they'd jokingly coddle up to her whenever she was around, making a mild pass at her from time to time. Those same friends would constantly say Tom and Lynne would one day get married, as they seemed perfect for each other. In those days, I agreed, but thought little of their plans for the future. I've always been under the impression that people grow until their late twenties/early thirties, and that couple don't last until then because people tend to grow in different directions.

After a while, it turned out I was right. After a few seemingly happy years and a very jagged breakup, they've been apart for a few months now. They tried mending things, but it just never came around.
I always had a thing for Lynne, but I never acted upon it. It always seemed slimy to me to make a pass at your friend's girl (even if you're just joking), even worse to actually fool around with her, and somewhat uncool to make a move after they break up. They loved each other, and it'd feel like betrayal to him and an unnecessary complication to her to do anything but keep one's distance.

They both live out of state now, so there's really no chance for me to make any kind of progress with her, even if I could get over my prejudices and do something. But what is accepted behavior, exactly? Or, if things changed in the future, when would it be okay to pursue, if ever?
This might sound like a case of oneitis, but I assure you it's not. Lynne's well outside of my priorities at this point, and I'm not putting my life on hold over something like this.

How would Tom take it?

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I don't know, that's the thing.

Generally, I think I would wait to the point to where they've both moved on and ready to see them date other people. But I'm not sure what it would do to you to see your best friend dating your ex.

He loved her, probably still does. When they broke up for the final time, he kind of leapt into his friends' arms for support (freely given, of course), then he went into remission for a while, then he actually did a bit of cathartic writing. He took a month to work on it, showed me a draft (he's the creative type; it was pretty good), then destroyed all copies of it, apparently embarrassed by it. Since then, Tom and Lynne hang out from time to time on a purely platonic basis.

Maybe this paints a picture. He's never been a violent person, or even the jealous type (it would seem). So ultimately, I don't know how he'd take it.

You are within your rights if it's over between the two of them. But if you don't talk to him about it, you're at risk at losing him as a friend. Even if he says it's okay, you two may not be friends eventually. So if this girl is worth it, go for it...just let him know.

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Don't. There are so many more women in the world to fuck up your social circle over one chick.

I agree with neo87 on this one. In most cases a friend is worth more than a female partner, and the way you describe your relationship with Tom shows that you definitely do care about this friendship. There are so many more women on this planet to not have to go there.

However, if you would insist on pursuing this, I would first talk with Tom about it. Not a simple phone call or text conversation, but invite him over, sit down and speak your mind. Even when he says he's fine with it, he might actually feel different about it so be careful in just taking his word if you take this friendship serious.

Stop dude.

If you were to act on this situation not only would you lose a friend but you would partially ruin your developing of an attractive mindset. Especially if you and the girl don't work out, which it is likely that it won't. This risk isn't worth the reward. I think that speaks for itself.

Cut it out man. have an abundance mentally. Do you know how many Lynne i've ran into one after the other after wondering if i'd ever meet another girl this cool again? They're everywhere. Just stop it man.

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Alright, it's final. I figured it wasn't a good idea, but I thought I'd confirm.

I posted this as a general question as to whether it's okay to do this with this particular Tom/Lynne case, or in general with friends and ex's. I think this is a general issue.
Thanks to everyone who answered.

You could just ask him if he'd be cool if you fucked her and see how he reacts to it... If he gets pissed about it, you've got your answer. If he's cool with it, you've got your answer.

Depending on what type of guy he is, he might be cool with it. I've had girls that I've passed on to buddies...

Sounds bad but the girls actually like it.

All those cocks. All that cum... 0 Judgement.