Leo dated supermodel Gisele Bündchen on and off between 1999 and 2005. Gisele was reportedly the one who called it quits, but in a 2009 Vanity Fair interview, she admitted that there were no hard feelings between them, saying, "We know what we had. We were very young, and we grew together in a lot of ways. We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best." Gisele went on to marry NFL star Tom Brady and remains the only woman Leo has brought as an award show date besides his mom, Irmelin, or his BFF Kate Winslet.