Leonardo DiCaprio's Dating History, From Naomi Campbell and Gigi Hadid to His Latest Fling

DiCaprio dated the supermodel on and off between 1999 and 2005. Bündchen was reportedly the one who called it quits, but in a 2009 Vanity Fair interview, she clarified 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." Bündchen went on to marry (and divorce) NFL star Tom Brady.