I can't even get a guy to text me back and Leo has, like, 2,332,939,293 sexy women surrounding him on the reg.
He's dated everyone from Bobbie Brown in 1993 to Blake Lively in 2011.
More than 20 years later, they still get together to look hot on vacation, save Russian tigers, and photobomb 50 Cent.
Kristen Zang, a model who dated Leo for two years (1996-1998), accompanied the actor to the premiere of Romeo Juilet.
"We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best," she told Access Hollywood in 2009.
Admit it – you’re intrigued by Leonardo Di Caprio’s dating history. We have said they were probably a thing UNTIL it was reported he'd been seeing 19-year-old Dutch Victoria's Secret Pink model, Chelsey Weimar. See Leo’s dating history - from 1994 (when he was 20) to now…
Although a source told The New York Daily News that Kristen was "the love of his life," she dumped him because of his immaturity and "posse of young model-hounds."The daughter of singer John Phillips, Bijou dated Leo in 1998.
He hooked her up with her first big Hollywood connection, director James Toback, who cast Bijou in his film Black and White.
But while a pretty face and slim figure are nothing unusual in Hollywood circles, the next requirement is rather more niche - they must be able to ride a bike...Leonardo Di Caprio is ready for adventure at a moment's notice.
The dynamic duo looked far from the glamour couple they are as they sauntered down the sidewalk in their scruffy ensembles.
He failed to take her as his date to the Oscars last month, even though they have been dating for around nine months.
Leonardo Di Caprio — who has reportedly been dating Nina Agdal for a while now — is rumored to be cheating on the 24-year-old with another bikini model. But now, almost six months later, it looks like the man has moved on… According to Page Six, Leonardo Di Caprio and his friends Lukas Haas and Tobey Maguire hung out with a bunch of models at Catch in LA.
Some eye-witnesses told Page Six, That's pretty cute (or disgusting!!! Page Six was told Leo's girlfriend was away on a modeling shoot while Paige and a group went back to Leo's place.