More times than not, going after your buddy’s ex is off limits and fully violates any type of guy code by which you might abide.

“Even if the two of them have split, emotions take a while to heal, so it’s unlikely that the friend is going to be okay with it.” But not all relationship experts see it this way.

“It’s ok to move in if they are estranged and no longer in love and divorcing,” says matchmaker Marla Martenson. It could be right under your nose, and circumstances have to shift for things to evolve.” As Martenson points out, “It’s a delicate situation, but why let a potential love match get away?

It’s also important to remember the evolving power of social norms.

Your friend may be OK with what’s happening at one point, but their feelings may change." Seriously, what is it about him or her that's worth potentially ending a friendship over? Do you think you two actually have a future together?

The news about Simon Cowell getting it on with his good friend’s wife — or estranged wife, depending on who you talk to — has sparked a great debate once again.

Under what circumstance is it acceptable to pursue your friend’s former love interest? because I just don’t see why of all the people in this world you need to choose to put yourself in such a complicated situation. Read on for Fox News Magazine editor Meghan Sharp’s guest blog about this very subject: Simon Cowell recently sparked some scandalous headlines when it emerged that he is set to become a father — with the wife of his close friend.

Your friend broke up yesterday and today you were seen romancing with his friend. Your already-devastated friend would get even more miserable.

If you are interested in your friend's ex, go slow and steady.

Assess the situation by putting yourself in their shoes and thinking about how you would react if the situation was flipped.

"The thing to remember is to be open about your feelings", says Dr. "Though you always run the risk of hurting others, no good ever comes from keeping secrets in these types of situations.

do when pursuing the exes of their best friends, or less-than-best friends, even.