Natasha Henstridge
Natasha Henstridge was not the first model DiCaprio was linked to, but because of her acting aspirations, it is with no wonder that their relationship wasn’t built for it to last. At the time when Natasha and Leonardo were introduced to each other, Leo was known to be at the edge of his acting career becoming an A-list star because of the release of Titanic. While on the other hand, Natasha had experienced her first success being an actress. These two never went out to the public with their romance.
Bijou Phillips
Leonardo DiCaprio seems to be a young man who is quite more experimental when it comes to his choice of taste with women. It is said that Phillips was not exactly the type of Leo. Leonardo DiCaprio usually prefers those leggy blonde models. Even so, their relationship was proved to be advantageous, no matter how short it was back then. Bijou Phillips came from a showbiz family, but it was Leonardo DiCaprio who made a way to connect her to the director that made her first film, Black and White.