2000: Virginie LeDoyen

Leo was linked to his French co-star Virginie LeDoyen since they worked together on The Beach,. Rumor has it that their on-screen chemistry carried over off set, but LeDoyen later dismissed it as tabloid exaggeration. She was far more focused on criticizing the overwhelming media frenzy and said she would “not wish” his level of fame on anyone.

2000–2005: Gisele Bündchen

Then came his first truly long-term relationship: five years with Gisele Bündchen. At the time, they were one of Hollywood’s hottest couples. After their relationship ended, Gisele wrote a memoir in which she revealed that while she was growing spiritually and personally, Leo generally stayed the same. So in the end she decided to move on. But but she credited the relationship with teaching her a lot about herself.

2005–2010: Bar Refaeli

Not long after Gisele, Leo started dating Israeli model Bar Refaeli. They were together on and off for about five years, meeting at a U2 party and quickly becoming a paparazzi staple. According to reports, the relationship ended when friends and family pushed for marriage and Leo wasn’t ready to commit.