He hooked her up with her first big Hollywood connection, director James Toback, who cast Bijou in his film Black and White.
Things ended with Leo, and she moved on to costar Elijah Wood.
Before Tom Brady, Gisele Bündchen dated Leo for five years, but ended it in 2005.
Leo's 1995 rumored fling with Naomi Campbell reportedly fizzled fast, but they became good friends.
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.
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.
The Oscar-winning actor, 41, has been dating 24-year-old Danish model Nina Agdal for the past two months, a source tells ET.
The two were caught showing plenty of PDA on the beach in Malibu, California, on Thursday, when the usually private Di Caprio was snapped giving Agdal a steamy smooch as she lay on the sand.
According to our source, things started to heat up between the attractive pair when they attended the Cannes Film Festival together in May.
He wore his signature newsboy cap and vaped as Kawalec was glued to her phone most of the evening.
The pack later celebrated Tao group partner Jonathan Schwartz’s birthday at Marquee, where, according to a spy, they appeared “couply. Leo was dancing with her in his arms and canoodling.
They were doing their thing, bumping and grinding.” A source close to Di Caprio told us it was just a typical night out for the star.
“Leo was with his friends all night and went home solo,” said the insider. This article originally appeared in the New York Post's Page Six.