Break-ups are messy, especially when the friendship fallout happens and sides are chosen. Although you may have hung out with your ex-boyfriend’s friends while you were dating him, chances are, if you two split, he is taking his entourage with him.

One of my best male friends from college dated this awesome girl freshman year to the end of junior year. When their relationship ended, I stopped talking to my buddy’s ex-girlfriend. I’d say “Hi” to her if I saw her on the street senior year or at a party, but it was always a hug and a “See Ya Later” once she was no longer his girl.

 I figured I knew him first and he needed to know I supported him and his decision. She became a good friend of mine during those three years they were dating, but it felt wrong to keep talking to her or seeing her. It came down to a respect issue for me and I decided to protect my friendship with him.

Read Do Guys Prefer Women With Big Boobs?

Then the two rekindled their feelings a month before graduation and everything went back to normal in terms of our friendship. The three of us acted like no time was lost at all.  If anything, my relationship with her grew stronger post-college since she lived in New York City too and he lived out of town. The three of us were back. Reunited. That was until they broke up again. When the second breakup happened, she and I just stopped talking. I stopped calling her and she stopped calling me. It was tough.

With my own ex-girlfriend it was an easy call for my guy friends. They hated her. I knew it and she knew it, even though I still tried to convince my ex that my friends liked her. So, when the two of us ended things my friends were happy they didn’t have to see her anymore and I’m sure she was happy she didn’t have to see them (and probably me) anymore, either. It all worked out.

But what if you really liked a friend of your ex-boyfriend’s, is there any chance your friendship still stands a chance after a breakup with his friend?

"Typically, it’s s a package deal and the breakup is not just the couple, but the shared friends as well. Real buddies have each other’s backs in any circumstance and the idea of staying close with his ex, especially without him knowing, is out of the question,” Booth, from Scranton, Pennsylvania, says. “Even if my buddy seems cool with my having a friendship with an ex, chances are he’s not. The reason I say that is because a lot of times guys will take the ‘high road’ just because they don’t want to appear insecure in front of their guy friends. But real buddies understand that about each other and there’s an unspoken respect thing that puts the brakes on any post-breakup friendship."