Chatting up a buddy’s lady can be a fun exercise in chivalry ‘ a few innocent jokes at your friend’s expense, the occasional flattery over a few drinks. Of course, all this falls under the category of friendship or good, clean fun. But what happens when your friend and his college sweetheart break it off? Is it fair game or something to steer clear?

1. Be upfront

Before proceeding, consider whether you should bring this up to the parties involved. Neglecting to do so may make you look foolish since some damage may already be done, and lingering suspicions may hurt your friendship once you bring up the possibility of the two of you together.

If he’s not a close friend, giving him a heads-up may seem unnecessary. But consider your reputation: Once you’re labeled untrustworthy around girlfriends, your close friends in relationships will take note. Losing their trust is not worth a one-night stand.

2. Taken just may be your type

Nothing is sexier than a woman you can’t have, but remember that it’s possible your interest is heightened by the danger of a scandal. Be sure to consider this before you pounce ‘ if she does leave her guy for you, the fantasy may be better than the reality. Give it some time for the dust to settle so you both know you’re doing the right thing.

3. The ex factor

Hooking up with a buddy’s ex is tough waters to charter. Codes and time lines do not replace your responsibility to address the issue head-on and there is no way to measure emotional capacity for recovery. Your friend may appear to be emotionally detached from his ex, but trying to gauge his reaction may prove crucial to determining your next move.

4. Eskimo brothers

Maybe the lady in question is a familiar face in your house. Never to sleep alone, she is familiar with quite a few of your roommates. It’s possible that your friend and her have set some boundaries like no hooking up with mutual friends. Whether she keeps her promise or not, you should always check before rubbing noses with your friend’s girl.

Mike Burzi, a senior majoring in finance and marketing, expressed his opinion on what constitutes a girl who is ‘fair game.’

‘If she has been with several of your friends and allows men to treat her unfairly, it’s safe to say you’re not stepping on anyone’s toes,’ Burzi said.

But let’s assume the worst: All your attempts to reach out to your friend have failed and you know he doesn’t approve, even though you’re spending a lot of time with his ex beau.

Dan Fischetti, a senior majoring in political science, feels it’s important to weigh the pros and cons of a delicate situation.

‘Things may never be the same between you and your friend, but you have to decide if she’s worth it,’ Fischetti said. ‘Time will ultimately tell.’