A Vicious Recycle

I'm a 30-year-old single guy. Two friends from college got divorced six months ago after being married to each other for less than a year (no kids or anything). The truth is, I had a crush on the woman before they even met, and I'm fairly sure the feeling was mutual. I'd like to ask her out, but I'm certain this will bring condemnation from all our mutual "bros," though I was never close with her husband. Does that trump the rule that you shouldn't date a guy friend's ex? Or is she off-limits forever?

--Wary

It's natural to want to express your sympathy to a guy whose marriage just broke up: "Hey, man, so sorry to hear you two didn't make it. By the way, did she happen to mention me?" Asking out a buddy's ex can seem like the dating version of poking your head over the booth divider at the diner and asking, "You gonna eat that?" It's especially unseemly to forage in the remains of a guy's relationship if he isn't exactly skipping away from it. But assuming the Jaws of Life aren't required to pry the guy out of the fetal position, a divorce is a breakup, not a "bent but still usable," meaning post-divorce, it's time for the ex-husband to release his ex-wife back into the wild. People typically advise choosing the friend over the girl (sometimes because they think they'll sound like bad people for advising otherwise), but you should consider what matters more to you -- possibly having a crack at her or maintaining your social cred. If you do go out with her, do it discreetly at first: Go places where people won't know you, and avoid the temptation to Facebook or live-blog your entire evening. If, after a few dates, you're hitting it off, it's a good idea to give the guy a heads-up via email. He might still be mad. But at least you'd just be a jerk, not a sneaky jerk. If it turns out you and she have something lasting, in time, people should begin to think of your relationship as something "meant to be" -- while perhaps hiding the silver and the women when you come around.