GISELE BUNDCHEN

DATED: 1999-2004 SPLIT: AGE 24

The model and the actor, then 19 and 25 respectively, made a striking duo when they got together in 1999. They dated for five years until they split in 2004, with Gisele later revealing she was going through a tough time.

“Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes.” Two years later the model met current hubby Tom Brady.