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Leonardo Di Caprio's Girlfriends

Wednesday, Aug 11, 2021, 7:30 pm

1.Jessica Simpson

Let's face it, Leonardo has probably dated every beautiful woman out there, so really there are too many to mention. Flings that didn't last long included Jessica Simpson who by all means fits the criteria he seems to look for in a woman.

2.Sienna Miller

Being blond, an actress and a model as well as Britain's 'It' Girl, made Sienna very datable in Leonardo's eyes. It appears he got stuck in when Jude and Sienna were not getting along very well.

3.Trishelle Cannatella

Of course he dated Trishelle Cannatella, she was a playboy model and lingerie model. So, that is to be expected.

4.Liv Tyler

A brunette at last! Leo and Liv hooked up when Liv was very much 'in trend', which seems typical in his choices. Although no one really knows all the juicy details this early 90's hookup seemed to centre around Liv playing a love scene with one of his best friends. Perhaps he asked for an introduction. Pushy fellow that he is.

5.Bridget Hall

These two hooked up during Bridget's famed Sport Illustrated swim-shoot shoot period. Both were doing well, so both were real hook-up material. The interesting fact about these two though, is that Leonardo was Bridget's first lover, she was a virgin. She said afterwards that the whole thing was disappointing. Gosh, Leo certainly doesn't have a great rep between the sheets.

6.Claire Danes

Another blond pretty actress, but this time things seemed a bit different. Claire and Leo met during the making of the film Romeo and Juliet and what a lovely couple they were in that movie. The couple took it too far and thought maybe that their love would translate into real life. It didn't.

7.Linnea dietrichson

If you thought 5 months was short how about 5 minutes? Leonardo picked up British Linnea dietrichson at a nightclub. They went home and Linnea cited that, 'It lasted all of 5 minutes then Leo fell asleep'. If that wasn't scathing even she added 'He looked pale flabby and fumbled a lot'.


8.Blake Lively

This was one of Leo's shortest relationships only lasting 5 months. Blake Lively broke up with him on his birthday. Poor Leo perhaps he needs to stop dating beautiful models with luscious bodies?

9.Gisele Bundchen

If she is hip and happening and of course a supermodel then she is bound to land up in Leonardo's little black book. Gisele and he had an off and on type of relationship finally breaking up for good in 2005.


10.Eva Herzigova

Beautiful Eva was better known as the 'Wonder Bra Girl'. Of course with her gorgeous wholesome looks, sweet personality and supermodel status Leonardo just had to have her. She apparently an affair to him while married to Tico Torres at the time.

11.Amber Valletta

Another memorable supermodel turned actress. Leonardo apparently saw her in Vogue, decided her wanted her and called the modeling agency! Some guys have all the luck right?


12.Helena Christensen

Leo has always seemed to gravitate toward beautiful models when choosing a mate. Helena Christensen is one of the most famous and long standing models of all time. She has that feline type of beauty with a lithe long body and exquisite face.


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