Celebrity romances come and go so often, it’s hard to get really attached to Hollywood couples. But who are we kidding, we’re suckers for certain ones, so when relationships crumble for our favorite stars, it makes the room a little dusty sometimes. With a Sandra Bullock-Jesse James divorce likely looming and ready to join the ranks of the most painful celebrity break-ups, here’s a look at 10 that hit us hard: 10.

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THG Presents: The Most Heartbreaking Celebrity Break-Ups