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Celebrity Breakups That Will Make You Glad You're Single

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October 11, 2009 - Bryan Bedder/Getty Images North America more pics like this »
9. Blake Lively and Penn Badgley

Gossip Girl fans hoped this romance would last forever, and for a while there, it seemed it might. Lively, who played Serena on the hit CW series, and Badgley, who played Dan, seemed to mimic their on-screen personas when they broke up right around the time Humpherwoodsen was no more.

No explanation was ever offered for their split, which kept fans obsessing over what exactly had gone down. Not cool, guys. Not cool.