You probably wouldn't have guessed, but the Hollywood dating pool is a lot smaller than it looks — so small, in fact, that celebrities often end up dating the same people.

Even more awkward than the idea of bumping into a former flame on the street? The idea of your best friend going out with one of your exes—who may or may not have broken your heart. Unfortunately, it's not that uncommon among celebs: this was the case for besties like Taylor Swift and Selena Gomez, Joe Jonas and Zayn Malik, and even more celebrity BFFs caught in the middle of infamous love triangles.

Check out our gallery above to see how these celebrity friendships fared after learning they dated the same person.