3. Bridget Hall
In 1994, very early on in Leo’s career, he was often seen canoodling with the gorgeous, young Bridget Hall. Bridget who, you ask. She isn’t very popular, but we can see what Leo saw in this gorgeous blonde.
By the age of 10, Hall was discovered and became a model. By 17, she was considered by Forbes to be one of the world’s highest paid supermodels. Hall covered magazines like Elle, Vogue and Harper’s Bazaar while modeling in huge campaigns for the likes of Guess Jeans and Pepsi Cola.