Me and my buddy were at the bar last month when Jeff's ex (call her Lisa) walked in. She saw us and came over to say hello. This wasn't any kind of bros before hoes thing; like I said, their breakup was friendly and we'd seen her around a few times since then. It was always friendly because Lisa's actually pretty cool. This time was different, though. She stuck around a lot longer and usual and was pretty clearly making eyes at my buddy. When she got up to leave, she gave him her number and told him to call her if he wanted to hang out.

So here's our question: is my boy crossing a line if he makes a play for Lisa? I know you're not really supposed to do that sort of thing, but it's been such a long time. I can't believe Jeff would actually get mad about it; he and his current lady are practically engaged. I say my buddy should go for it, but he has some misgivings. I don't think she's playing games or anything; it seems like she genuinely digs him.

Thoughts?

Bro in Bangor

Dear Bro,

Oh, the tangled webs we weave.

Your pal has found himself in quite a little predicament, hasn't he? Navigating the dating world is difficult enough without the added pressure of potential friendship ruination. Makes you wonder if that young lady knew what kind of Pandora's box she was opening.

You're doing your buddy a solid by encouraging him here. I definitely understand his misgivings, but the truth is that there has to be a statute of limitations on this sort of thing. It'd be different if Jeff was still locked in his bedroom, singing Dio songs into a hairbrush and using black ink and black paper to write fitful verses of angsty bleakness in the key of Lisa. But he's not. He's moved into what sounds like a happy, stable, fulfilling relationship. So he shouldn't give a crap.

But he might.

It all boils down to what kind of character your boy Jeff has. If he's really happy now, he should also be happy that your buddy has a shot at something special. It might be a little awkward at first, but things will work out just fine. However, if Jeff is the possessive type, he might resent your friend for making a connection that he himself couldn't maintain.

It seems clear that this isn't really an argument. You're just looking for me to tell you that what you want to do is okay. It is. Whether Jeff will be okay with it? That's another story.

The heart wants what it wants, bro. If love and happiness is an option, you have to take a swing. Jeff's just going to have to suck it up.