Leonardo DiCaprio’s Dating Back-Catalogue

We all know that Leonardo DiCaprio is a big fan of the ladies and it goes without saying that he is never lacking in the dating department, with a huge bevy of beautiful women constantly waiting in the wings to be his next conquest. However, there are a few women who have managed to tame the award-winning actor, albeit just for a few years at a time. Here are just a few of his most influential girlfriends…

1. Bridget Hall

The first in a long line of Victoria’s Secret Angels, Bridget Hall was widely considered one of Leo’s first semi-serious girlfriends when they were spotted in and around New York together in 1994. Sadly the romance was short-lived but his love of beautiful models was only just beginning.

Leo's dating back-catalogue

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2. Brittany Daniel

Next up on Leo’s dating roster was his co-star from breakthrough movie The Basketball Diaries, Brittany Daniel. You might also remember this stunning blonde beauty as one half of the twins from 90s TV series, Sweet Valley High.

leonardo dicaprio girlfriends

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3. Kristen Zang

The first of a couple of ladies who managed to secure Leo’s affections for longer than a year, Kristen Zang dated him from 1996-1997 and he even took her to the premiere of his hit movie, Romeo + Juliet.

Leo's dating back-catalogue

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4. Gisele Bündchen

Still arguably the great romance of Leo’s life, Gisele Bündchen was his girlfriend for five years only to see it end in 2005 when there were rumours that she wanted to get engaged. Perhaps this was for the best because, aside from her now being happily married to football star Tom Brady, their children might have been way too beautiful anyway.

Leo's dating back-catalogue

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5. Bar Refaeli

This is a bit of a tough one to call because these two were on-again-off-again for six years, from 2005-2011. But there is no denying that Bar Rafaeli fits the Leo dating-spec perfectly: Victoria’s Secret model? Check. Blonde hair? Check. A love of basketball and cycling around New York? Check.

Leo's dating back-catalogue

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6. Blake Lively

One of only a few non-models to make it in to Leo’s little black book, actress Blake Lively spent a short time being swept off her feet by Leo in 2011 only for it to end after five months.

Leo's dating back-catalogue

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7. Toni Garrn

2014 saw Leo vaguely settle down with yet another Victoria’s Secret model, Toni Garrn, who was 22 years-old at the time (18 years his junior). But alas it wasn’t meant to be with the couple parting ways after nearly a year when Leo was seen leaving a club with a group of twenty girls.

Leo's dating back-catalogue

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8. Rihanna

Certainly one of the most intriguing ‘romances’ of 2016, nobody quite knew whether Rihanna and Leo were actually a ‘thing’ but they were certainly spotted out looking decidedly flirtatious on several occasions.

Leo's dating back-catalogue

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9. Nina Agdal

Leo’s current girlfriend Nina Agdal (yet again another Victoria’s Secret model) might just be the one to tame him after he was pictured comforting her in August 2016 when the pair were involved in a minor car crash. Thankfully no one was hurt but these adorable photos made headlines all over the world and his lovable caring side got people thinking that he might just be ready to settle down. We’ll have to wait and see.

Leo's dating back-catalogue

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10. A special mention for Kate Winslet.

Although these two have never gotten together in real life they have kept the world on its toes for over 20 years with their amazingly sweet and loyal friendship. Apparently Leo even gave Kate a ring (something no other girlfriend has managed to get him to do) after filming wrapped on their movie Revolutionary Road and only the two of them know what it says. I don’t think fans of these two will ever stop hoping that they’ll get it together one day but for now we’ll just have to enjoy their cute red carpet appearances.

Leo's dating back-catalogue

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