Remember that one time Leonardo DiCaprio [1] brought a girlfriend as his date to the Oscars? Yeah, we almost didn't either. But it really happened! The Hollywood heartthrob was dating [2] supermodel Gisele Bündchen [3] 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 [4]), 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 [5] his first Oscar until 2016.
Leo and Gisele dated on and off between 1999 and 2005, and while their split was reportedly amicable [7], 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 [8] Leo has ever brought as an award show date. Keep reading to relive the historic moment.
