The one that started it all. Leo got his first taste of dating a Victoria’s Secret model when he and Bridget hooked up in 1994.

The Oscar-winning actor and Naomi had a blink-and-you’ll-miss-it tangle in 1995 before deciding they were better off as friends.

Helena caught Leo’s eye at their height of his fame in 1997 when Titanic came out but their fling only lasted a few months.

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The Czech stunner only dated Leo for two months in 1998. Was he that bad, Eva?

Gisele and Leo were the golden couple of the early aughts but the Brazilian beauty reportedly got tired of waiting for him to propose and the pair called it quits in 2005.

Leo’s sixth Victoria’s Secret romance, this one definitely raised the bar! They dated for a whopping 6 years, which is ages in our books.

(Read more: 10 Famous Couples That Found Love On A Movie Set Then Broke Up)

Leo continued to play Russian roulette with his love life, dating Anne V briefly in 2009.

Leggy, blonde and beautiful, Erin should’ve been perfect for Leo but the pair were together for only 10 months in 2012.

This gorgeous German-born model had a low-key relationship with the actor in 2013 but they ultimately couldn’t make it work.

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Will 10 be Leo’s lucky number? Nina certainly has what it takes to be a leading lady. Blonde hair? Blue eyes? Banging body? Check, check and check!