Leonardo DiCaprio Has Never Done This With Any Other Girlfriend But Gisele Bündchen

Remember that one time Leonardo DiCaprio brought a girlfriend as his date to the Oscars? Yeah, we almost didn't either. But it really happened! The Hollywood heartthrob was dating supermodel Gisele Bündchen when he received a best actor nomination for his role in The Aviator back in 2005. Instead of bringing his mom, Irmelin (or his BFF Kate Winslet), as he normally does, he brought Gisele. Dressed in a white strapless Dior gown, Gisele was all smiles as she practically floated down the red carpet on Leo's arm. Unfortunately, Leo went home without an award that night — as we all know, he didn't end up winning his first Oscar until 2016.

Leo and Gisele dated on and off between 1999 and 2005, and while their split was reportedly amicable, Gisele was the one who called it quits. "We know what we had. We were very young, and we grew together in a lot of ways," she said in a 2009 Vanity Fair interview. "We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best." To this day, Gisele is the only girlfriend Leo has ever brought as an award show date. Keep reading to relive the historic moment.