Gisele Bündchen Is Still Leonardo DiCaprio's Longest Relationship

Leonardo DiCaprio seems to be Hollywood's forever bachelor, perhaps snatching the title from George Clooney, who was previously known to date beautiful women but hadn't been very interested in getting married — until he met Amal Alamuddin, that is. DiCaprio has dated several high profile women in the entertainment industry over the years, from Blake Lively to supermodel Anne Vyalitsyna, according to Elle, but he just hasn't found the one with whom he wants to spend the rest of his life. 

DiCaprio has vacillated between quick romances and long-term relationships, but he has yet to get down on one knee. Regardless, some of his relationships were incredibly serious, and a handful even spanned several years. In 2006, for example, DiCaprio dated model Bar Refaeli. The two were together for five years, less a six-month break, before going their separate ways in 2011, a source confirmed to People at the time. 

To date, however, DiCaprio's longest relationship was with supermodel Gisele Bündchen. The two dated from 1999 until 2005 when Bündchen broke things off.

Leonardo DiCaprio and Gisele Bündchen were together for about 6 years

Leonardo DiCaprio and Gisele Bündchen were one of the hottest couples of the early 2000s. DiCaprio reportedly sought out the supermodel after watching her walk a runway show, per InStyle. Their relationship was like lightning in a bottle and there's one surefire way that we all know the two were serious. To this day, Bündchen is the only woman DiCaprio ever brought with him to the Oscars. The year was 2005. "It was nice to experience that once in a lifetime, and I love that dress," Bündchen told British Vogue in May 2022.

But, while love seemed to be buzzing around these two beautiful people, things came to an abrupt end after six years. We didn't know the reasons behind the split at the time, but Bündchen shared the details in her book, "Lessons: My Path to a Meaningful Life," which was released in 2019. "No longer numbing myself with smoking, drinking and too much work, I was becoming more and more aware of things that I'd chosen not to look at. Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes," Bündchen wrote (via E! News). Bündchen would go on to marry former NFL quarterback Tom Brady and start a family, while DiCaprio continued on his quest to find a new love.

Leonardo DiCaprio and Gisele Bündchen are technically both single

Leonardo DiCaprio has never been one to speak out about his personal life, keeping things professional and work-focused at every turn, but his romances always seem to make headlines. With Gisele Bündchen's split from Tom Brady in 2022, some fans may have been wondering if this would open the door for a reconciliation a la Jennifer Lopez and Ben Affleck. However, while it's possible that Bündchen may have been the one that got away, DiCaprio and Bündchen haven't made any public moves to give their love another go more than 15 years later. 

DiCaprio split from Camila Morrone in 2022 after four years of dating, according to People, and while he was spotted with 19-year-old model Eden Polani, sources tell TMZ that the two aren't actually dating. But it looks like Bündchen isn't looking in the rearview mirror at the present time. The Brazilian beauty has been romantically linked to jiu-jitsu instructor Joaquim Valente since filing for divorce from Brady. It's only a matter of time before DiCaprio finds another woman to spend his time with, but will she be the one that ends his eternal bachelor ways? We'll have to wait and see.