12 TV Breakups that Left Us All Traumatized (5 of 7)

8. Blair and Chuck, Gossip Girl

Blair and Chuck were one of those on-again-off-again couples that could never seem to decide what they wanted in their relationship. It certainly didn’t help when Blair hooked up with Chuck’s sketchy Uncle Jack, which happened after Jack agreed to hand over ownership of his hotel to his nephew in exchange for a night with his girl. Not surprisingly, Blair and Chuck did end up getting married in the series finale because Manhattan kids are going to do what Manhattan kids want to do.

9. Rory and Dean, Gilmore Girls

This is a somewhat controversial pick as Rory’s breakup with Jess was something that left a lot of viewers devastated — especially when Rory confessed that she loved him but didn’t want to be with him anyway. But still, Dean was Rory’s first love, and the first breakup tend to cause the most heartbreak.