A Definitive Timeline Of Leonardo DiCaprio's Dating History From his problem with dating a model love to the woman he's reportedly ready to marry - by Katie Douglass 30 Nov After a string of flings and relationships, rumours are flying around that Hollywood's most notorious bachelor Leonardo DiCaprio is finally ready to settle down and pop the question to his girlfriend Camila Morrone.
Below, we've compiled a timeline of the Oscar-winning actor's dating history. Naomi Campbell The actor reportedly had a fling with the supermodel back inhowever they went on to become good friends and even spotted hanging out on a yacht in However, the pair broke up after Zang dumped him for his lack of maturity and "posse of young model-hounds.
Toni Garrn Leo dated the Victoria's Secret model for 18 months until they broke up in According to tabloids, Garrn broke it off after Leo was spotted leaving a Miami nightclub with 20 women. Rihanna Hollywood was abuzz when DiCaprio was seen with the singer at numerous Hollywood parties in Magazine and said, "Everyone was just having fun - there was a lot of dancing.
The actor was photographed leaving a Los Angeles club with Perkins and spotted hopping into a car together.
You see models on television, in ads. They're in commercials, they're in movies, and it's like, “It would be so cool to date a model because I would get all this. I eventually decided that dating a model was potentially a I've heard this is often an issue with people who work in industries where you get.