A Timeline Of Leonardo DiCaprio and Brad Pitt's Dating History ⋆

A Timeline Of Leonardo DiCaprio and Brad Pitt’s Dating History

Leonardo DiCaprio is one talented individual who has had one of the most successful acting careers since way back in 1990.

He has a long list of Award-winning movies on his resume and an even longer list of Victoria Secret model girlfriends. With his Gatsby charm and Romeo romance, there’s no wonder his dating history is richer than anyone in the business! Let’s take a look at all the girls that have been in Leo’s life.

Bridget Hall

The first on the list is Bridget Gall. These two were linked in 1994 and she was the first Victoria Secret model he would date but by no means the last.

The two were young, beautiful, and famous and were spotted out and about several times in New York strolling hand in hand.

Brittany Daniel

In 1994 Leo also got cozy with Brittany Daniel, his co-star in his breakout film “The Basketball Diaries.

Though it would not last very long, it was short, sweet and passionate and not surprising considering the very steamy scenes between the two on-screen.