Jesus Christ Leo, can you please give us a chance?
Fresh off the back of his well deserved Oscar’s win, we thought it was high time we rubbed in Leo’s success just a little bit more with a look back through his dating history. Needless to say, in between shooting epic films and campaigning to save the planet, the man does extremely well with the ladies Victoria’s Secret models.
1993: Kate Moss
Leo started off his supermodel binge in style, bedding one of the most well known models of all time in Kate Moss. The relationship was apparently casual and short lived, but he got it done nonetheless.
https://www.instagram.com/p/BDw6Ckat4M5
1994: Bridget Hall
As a 19 year old, Leo bedded barely legal 16 year old model Bridget Hall – apparently breaking it off with her soon thereafter.
1994: Brittany Daniel
You might know her from White Chicks, Leo knows her from His Bed as a young whipper snapper.
https://www.instagram.com/p/_ZcrsSEjt9
1995: Naomi Campbell
One of the most recognisable supermodels of the 90’s, the two were rumoured to have had a fling in ’95 as both were hitting their straps career wise. (We don’t think he’s slept with DJ Khaled #major )
https://www.instagram.com/p/BdnQjzzHUEp/?taken-by=iamnaomicampbell
1996: Kristen Zang
His first proper girlfriend, the two dated for a year and DiCaprio took Zang to the premiere of Romeo & Juliet, so I guess you could say things were pretty serious.
https://www.instagram.com/p/BDs13foG9BM/?hl=en&tagged=kristenzang
1997: Helena Christensen
Leo supposedly hooked up with the 28 year old Danish bombshell/actress when he was a spritely 23. The pair were getting it on around the release of Titanic in 1997.
https://www.instagram.com/p/BAVA5WhhSs6
1997: Natasha Henstridge
Henstridge looked set to have a big career ahead of her after dating DiCaprio and starring in The Whole Nine Yards. Unfortunately her career went the opposite direction of Leo’s.
https://www.instagram.com/p/BDTYaTnywc8
1997: Demi Moore
As she was winding up her marriage with Bruce Willis, it was reported that Moore was spending time with DiCaprio. Discussing acting no doubt (or her penchant for younger men).
1998: Amber Valletta
Valletta is known as an actress who has done a little bit of everything but just never quite made it. She did however, manage to make it into Leo’s black book.
https://www.instagram.com/p/BcdfZTZgNnb/?taken-by=ambervalletta
1998: Bijou Phillips
The two met partying with DiCaprio’s infamous ‘Pussy Posse’ and briefly dated before she dropped him for Elijah Wood. Interesting call Bijou.
https://www.instagram.com/p/3DJXdDwewy
1998: Eva Herzigova
It’s around this time that Leo hits a purple patch (which happens to have continued unblemished for 18 years), starting out with the original Wonderbra model, Czech Eva Herzigova.
https://www.instagram.com/p/7i31hvGS0T/
2000: Gisele Bündchen
Gisele really needs no introduction. The two had a widely publicised five year on-again off-again relationship before she wifed up for one of the only men in the world who can compete with Leo in the dating game, Tom Brady.
https://www.instagram.com/p/BCWOd6AHjjc
2005: Bar Refaeli
Leo backed up one of his longest relationships with another one, seeing Israeli stunner and VS model Bar Refaeli for a number of years before realising that there were other models he had to see feel before he died.
https://www.instagram.com/p/BcxB_sVngdv/?taken-by=barrefaeli
2009: Anne Vyalitsyna
Leo took a break from the VS models when he briefly saw Sports Illustrated model Anne Vyalitsyna.
https://www.instagram.com/p/BcVUMWWAdHZ/?taken-by=annev
2009: Ashley Roberts
Leo bedded ex Pussycat Doll Roberts while on the rebound from Refaeli, an out of character digression from the model theme.
https://www.instagram.com/p/BCBW1SLqOnh
2011: Blake Lively
The two dated for about five months before parting ways. Ryan Reynolds quickly swooped in on Lively, one of the sexiest women alive. Good move Ryan.
https://www.instagram.com/p/BTE7f2cgLXL/?taken-by=blakelively
2011:Â Kendal Schuler
Moving on quickly from Lively, Leo turned his focus on Australian model Kendal Schuler, bloody good on him.
https://www.instagram.com/p/BcYyP9IlpzQ/?taken-by=kendalleeschuler
2011: Mădălina Diana Ghenea
Adding to his list of countries ticked off, Leo briefly dated (for a few weeks) Romanian model Ghenea in 2011 while shooting The Great Gatsby.
https://www.instagram.com/p/BDOnImAoNJI
2011: Erin Heatherton
Some of his finest work here. Leo and Erin were together for almost a year before they realised their schedules just wouldn’t work. Most of us would probably just adjust our schedules for Heatherton.
https://www.instagram.com/p/BbzkqRPl-He/?taken-by=erinheathertonlegit
2013: Barbara Palvin
It must get awkward when Leo’s name comes up down at the Victoria’s Secret runway. Another year another supermodel. Sigh.
https://www.instagram.com/p/Bcx_0FegdWP/?taken-by=realbarbarapalvin
2013: Toni Garrn
And another one…
https://www.instagram.com/p/BDnuweKDT_G
2015: Kelly Rohrbach
You’ll be seeing Rohrbach in the upcoming Baywatch film, Leo has already seen plenty of her.
https://www.instagram.com/p/BclCgUeBM4J/?taken-by=kellyrohrbach
2015: Rihanna
And to cap it all off, turns out Leo has been seeing RiRi on the side for the past few years as well. Damn son.
