Leonardo DiCaprio And His Ladies Over The Last Two Decades

Leonardo DiCaprio has captivated the public's attention since the highly acclaimed release of Titanic. He suddenly found his place cemented as a young heartthrob for a wide swath of young women. Leo quickly became accustomed to dating models, several of whom accompanied him to some of his biggest premieres. However, even though some of these women may have truly been the love of his life, for his biggest hit, the only lady he had on his arm was his co-star, Kate Winslet. It wouldn't be long before Leo worked his way through the ranks of supermodels, reeling in women who were ever more accomplished. But which lady truly owns his heart?

Leonardo DiCaprio may have achieved heartthrob status when he was barely 20 years old, but more than two decades later, he's still embarking on romances with some of the most beautiful models in the world. Leo's passion for models started young, as he was happy to trot out Bridget Hall as his first public girlfriend, all the way back in 1994. Sadly, their puppy love was not to last. So which leading lady is truly the love of his life?

When Leo began filming The Basketball Diaries in 1995, he had a new female costar to whom he could be romantically linked. As Leo's profile as an actor continued to rise, it's no surprise that the young heartthrob was all over the news for his romantic ties. Neither Leo nor Brittany ever confirmed their relationship, but considering their on-screen chemistry, there's some possibility that the two had a fling while they were working together on the film.

Claire Danes may have a high-profile husband of her own nowadays, but back when she was a teenager, she was the on-screen love of Leonardo DiCaprio. The rumors about their on-set relationship run the gamut. Some sources claim that though Claire was only 16, she found 22-year-old Leo unprofessional. That's a stark contrast to her recent confession that she had a crush on him while they were filming Romeo + Juliet. Danes implies nothing happened, but it's hard to know for certain.

As Leo's career ramped up in the mid-1990s with hits like Romeo+Juliet, it was only natural that he searched for the biggest names at the Victoria's Secret Fashion Show. Helena Christiansen may be one of the best known Angels, even today, but back in 1997, she was possibly even a bigger name than Leonardo DiCaprio himself. He may not have ever made things public, but it was pretty clear something was going on based on the number of parties they attended together.