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He saw Amber in a magazine he was reading and tracked her down.They dated briefly in 1998, although it didn’t last long, according to reports.The year was 1995, when rumors were sparked that Leo had been seen with supermodel, Naomi Campbell.

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Kristen Zang dated Leo for two years back in the day. We don’t know if she regrets it, but she actually finished with Leo, apparently because he was too immature for her!

Surprise surprise, another Victoria’s Secret model, this time, it’s Helena Christensen.

He’s dated Victoria’s Secret Angels, actresses, singers; and why wouldn’t he? He may only be in his early forties, but Leo certainly has a knack for landing beautiful girlfriends.

Here are 20 of the lucky ladies, and some even lasted a few years…

Some say that Madalina was the hottest girl Leo ever dated, even though she wasn’t really his type.

He met her after breaking up with Blake, and they met while he was shooting The Great Gatsby in Australia.Ahh, young love, and just look at how spritely Leo looks in this one!She was his first model girlfriend, and got dumped by Leo back in 1998, after four years together, on-and-off.What a surprise, another blonde in the mix for Lea.He dated this stunner in 1994, and apparently she seduced him, and not the other way round!Perhaps not the Leo type, not being blonde and all, but apparently he fell for Bijou. As per usual it seems for Leo, things didn’t last long, and she moved in soon enough to date he co-star, Elijah Wood.

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