Leonardo DiCaprio's Ex Girlfriends All Have One Thing In Common

It's a well known fact that Leonardo DiCaprio is a bit of a womaniser. But I mean, who could blame him? Well in honour of his Oscar win, we thought we'd take a look at all the women he's dated over the years on his way to Academy Award success and see what they have in common. We know he's just been holding out for Kate Winslet though, so it's totally fine.

1993: Bobbie Brown

Leo's first lady friend in Hollywood was Bobbie Brown, star of the famous Cherry Pie music video.

1993: Kate Moss

The two had a “casual” relationship in NYC when they were 20. Nothing too exciting or serious.

1994: Bridget Hall

Leo has really started to hone in on his type: models. This was a super casual thing though.

1994: Brittany Daniel

The two met while filming The Basketball Diaries, and dated casually (shocking) after.

1995: Naomi Campbell

A very high profile fling, Naomi Campbell and Leo remain friends to this day.

1996: Kristen Zang

Leo actually lasted a couple of years with model Kristen Zang until 1998, though it was on and off the whole time. It didn't last.

1997: Helena Christensen

Helena was one of the models that was rumoured to be getting with Leo while he was still with Kristen Zang.

1997: Natasha Henstridge

Another model...Really Leo, the theme is becoming obvious.

1997: Demi Moore

Demi was rumoured to have had a brief thing with Leo while going through her divorce from Bruce Willis.

1998: Amber Valletta

After a brief break from modelising, Leo returned with supermodel Amber Valetta.

1998: Bijou Phillips

The two dated for a time, with Leo helping Bijou get into acting. She ended things and started dating Elijah Woods not long after.

1998: Eva Herzigova

The Victoria’s Secret Model reportedly had a month-long affair with Leo while she was married.

2000: Gisele Bündchen

These two were on and off for just over five years - one of the longest relationships Leo had been in.

2005: Bar Refaeli

Leo was on and off with Israeli model Bar Refaeli for about six years. When neither of them wanted to settle down, they just realized being together was pointless. Leo's longest relationship to date that we know about.

2009: Anne Vyalitsyna

Leo dated Russian model Anne Vyalitsyna during a break with Bar Refaeli.

2009: Ashley Roberts

The Pussycat Doll was allegedly one of Leo’s rebound girls after his relationship with Bar.

2011: Blake Lively

Leonardo briefly dated Blake Lively for about five months before calling it quits.

2011: Kendal Schuler

After he officially ended things with Blake Lively, Leo spent some time with Australian model Kendal Schuler.

2011: Mădălina Diana Ghenea

Leo met Romanian model Mădălina Diana Ghenea while shooting “Great Gatsby” in Australia. The two dated for a couple of weeks and then it was a wrap for that. A brunette, for once Leo!

2011: Erin Heatherton

Leo dated this Victoria Secret Model for nearly a year, but their schedules were too busy to make it work with one another.

2013: Barbara Palvin

After dating Justin Bieber, supermodel Barbara Palvin met Leo when she was just 19.

2013: Toni Garrn

Toni Garrn was 23 when she started dating Leo back in 2013, but they soon split after she kept catching him with more models. It was reportedly when Leo was with 20 women at a Miami nightclub that they officially broke up.

2015: Kelly Rohrbach

The Sports Illustrated model met Leo back in 2015, and it seemed like things were getting serious when engagement rumors started popping up. Those rumors, of course, ended up being false, and they broke up before the year ended.

2015: Rihanna

Rihanna and Leo were spotted getting close at a Paris nightclub in 2015, but they’ve been allegedly messing around for even longer. The two have never denied anything, and clearly, their friendship is a mutual agreement.