Zimbio, in photo: Gisele Bundchen, boyfriend Leonardo DiCaprio
4. Gisele Bundchen dated Leonardo DiCaprio
2000 - 2005

Actor Leonardo DiCaprio and model Gisele Bundchen had an on-again-off-again relationship from 2000 through 2005. Sources close to the couple say that Gisele eventually got tired of Leo's party-boy habits.