His past dating history includes models Gisele Bundchen, Bar Refaeli, Erin Heatherton, Kristen Zang and Emma Miller — and they just keep getting younger and younger (Toni is currently 22-years-old). In her dreams...) Us Weekly was one of the first outlets to report the split.RELATED STORY: Leonardo Di Caprio’s a Rapper Now — and He Has That in Common With These 5 Stars So which up-and-comer will the Oscar nominee seek out next?
Leonardo’s longest run was probably his five-year relationship with supermodel Bar Refaeli.Media reports suggested that he took her virginity, something she has vehemently denied.FYI – Bridget was Leo’s first foray with a Victoria’s Secret model.If you know anything about Leonardo Di Caprio's dating history, it's probably that he tends to date blond models. They were most recently seen having lunch together yesterday in NYC.(His long list of exes includes Gisele Bundchen, Bar Refaeli, and, most recently, Nina Agdal, to name a few.) Now the actor appears to have a new love interest, and she's actually a brunette this time—but she's still a model. A witness said the pair "seem like an item" and Leo tried to make a low-key exit with "his hat over his eyes." The two were also reportedly spotted visiting Mo MA PS1 together, and Rae was also seen riding Citi Bikes with the actor last week.Leonardo Di Caprio is one of Hollywood's biggest stars - and he's certainly never been short of girlfriends.