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For the vast majority of us, the expression “There are plenty of fish in the sea” is meant to provide encouragement and proper perspective when our relationships don’t work out. Don’t give up; there are lots of guys, girls and mermaids who are just dying to date you. You just need to purchase yourself a high-quality fishing net or something. But when you’re a regular swell like Leonardo DiCaprio, this expression takes on an entirely new meaning. You see, we struggled mightily while researching this article and were only able to find 24 girls that have dated Leo, but all we can do is accept this and move on.
1. Bridget Hall
A model and actress, Hall was DiCaprio’s first legitimate girlfriend after having achieved a certain amount of fame. They dated in 1994, and it was rumored that Leo dumped her because she wasn’t impressed with his performance in the sack. Of course, she denies anything took place at all. But one thing is certain: after their breakup, he never dated a supermodel ever again. Except that I’m completely lying.
2. Brittany Daniel
These lovebirds met on the set of The Basketball Diaries, but when it became abundantly clear that Leo wasn’t the basketball hotshot that he pretended to be in the movie, the relationship was doomed. Or more likely they just realized they weren’t made for each other.
3. Naomi Campbell
In 1995, when DiCaprio dated one of the world’s most famous supermodels of that time, it marked the last time he would be with somebody who was arguably more famous than he was. It was, of course, the huge billion-dollar blockbuster The Beach that would turn Leo into the A-list actor we are all jealous of today.
4. Kristen Zang
If you care to know, Kristen Zang is a leggy supermodel. But, really, couldn’t that be said of literally every supermodel except for those who happened to have been born a mermaid? It’s been said that Leo was completely head-over-heels for Zang — the fact that they dated for nearly two years would seem to support this — but ultimately she found that he lacked maturity. And he seemed to enjoy the company of other young supermodels. She wasn’t too interested in playing the 12th fiddle.
5. Helena Christensen
There isn’t a whole lot to say about Miss Christensen — who was (surprise!) yet another model — other than the fact that she realized Leo was nothing like the Jack Dawson whom she had watched dying of hyperthermia over and over again during repeated viewings of Titanic.
6. Natasha Henstridge
Henstridge might not be a household name, but there was a time when you might have been able to recognize her as the chick who was secretly a repulsive insect-looking alien in Species. Their relationship didn’t last long. Perhaps she really was from another planet, and Leo couldn’t come to terms with this? Who knows.
7. Amber Valletta
Amber’s “Dating DiCaprio Origin Story” is a bit bonkers. Reportedly, he saw a photo of her in a magazine and flat out decided he wanted her. No — he needed her. When you’re Leo, you can do things like that.
8. Bijou Phillips
Phillips was the daughter of John Phillips, the singer from The Mamas & the Papas and…you can totally look up on Wikipedia if you care to know their story. Interestingly enough, she dumped DiCaprio for Elijah Wood, who possesses the largest eyes of any non-owl on the planet. She ended up marrying Danny Masterson, who you might know as the guy who’s in a heap load of trouble at the moment.
9. Eva Herzigova
Leo’s relationship with Herzigova wasn’t ever completely confirmed, perhaps because during the period of time in which they supposedly had a fling, she was married to a member of rock band Bon Jovi. Not Jon Bon Jovi himself. And not Richie Sambora. So it would have had to have been one of the other dudes.
10. Gisele Bündchen
DiCaprio and Bündchen were together for a whopping 5 years, which is the equivalent to eternity when measured in Leonardo DiCaprio Years.
