A young star in her own right, Claire Danes and Leo not only starred in Romeo + Juliet, but had an off-screen romance (though never made official) from 1995-96, proving you can mix work with play.
(Photo by Frazer Harrison/Getty Images)Dicaprio was the one of the biggest stars in 1997 thanks to the movie Titanic having worldwide success—and his dating resume reflected that that year.
Leo scored Danish model Helena Christensen, with the two getting together a few times.
(Photo by Gareth Cattermole/Getty Images)In case anyone doubted the actor’s skills, his relationship with actress Amber Valetta is one of legends.
Rumor has it Leo saw Amber in an ad for which she was modeling for and told his people to contact her people—which they did, as the two got together.
(Photo by Toby Canham/Getty Images)She might be best known as Mrs. Tom Brady these days, but the model and actor had a steamy relationship for about five years before finally calling it quits in 2005.
(Photo by Frazer Harrison/Getty Images for AFI)Actress Sienna Miller has had a relationship with Tom Sturridge for a few years now, but before dating both him and famously Jude Law, she allegedly had a short fling with Leonardo DiCaprio in 2005.
(Photo by Ben Pruchnie/Getty Images)After the two met backstage at a U2 concert in 2006, they had an on-again, off-again relationship for five years.
(Photo by Ethan Miller/Getty Images for Sports Illustrated)A member of the Pussycat Dolls, Ashley Roberts was able to dance her way into Leo’s heart—well, for a short time, anyway—as the actor spent some time with Ashley in 2009 during a break in his relationship with Bar Refaeli.
(Photo by Alberto E. Rodriguez/Getty Images)The last of Leo’s flings while on a break with Bar Refaeli, model Anne Vyalitsyna became arm candy with Leo for a short time in 2009.
(Photo by Michael Loccisano/Getty Images for Sports Illustrated)While she’s married to Ryan Reynolds now, actress Blake Lively was actually the rebound girl for Leo following his final break-up with Bar Refaeli, with the two hanging out for about five months.
(Photo by Kevin Winter/Getty Images)Yet another beauty that DiCaprio has been linked to
(Photo by Gaye Gerard/Getty Images)One of the most stunning ladies on the planet, Leo was able to balance work and play while filming The Great Gatsby a few years ago, finding time to hang out with his Aussie girlfriend Madalina Ghenea, with whom he dated for a few months while shooting the picture.
(Photo by Ian Gavan/Getty Images)DiCaprio found himself cuddled next to Victoria’s Secret model Erin Heatherton for nearly a year from 2011 to 2012, with the actor calling things off because of their busy schedules.
(Photo by Charley Gallay/Getty Images for Victoria’s Secret)With quite the list of supermodels and actresses, Leo’s current girlfriend is another model, the German-born Toni Garrn.
Together since May, 2013, the two are approaching their one-year anniversary—which, based on some of these other relationships—is quite the feat for the actor.
(Photo by Ian Gavan/Getty Images)
