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Unlike many of the women on this list, Toni and Leo were actually in a relationship for a while.The two were an item from 2013 to 2014 and were seen all over the world together.Leo and Erin were seeing each other from 2011 to 2012 – one of the longer relationships he has had. Erin, yet another blonde model, captured Leo’s eye much like previous women in his life.She was part of the Victoria’s Secret modeling group and was featured on their website as well as their 2008 fashion show.In 2012, Margarita and Leo were spotted kissing on board a yacht – his usual MO.Leo loves borrowing his friends boats and cruising around various countries around the world.Going on and on the blonde model front, Leo was said to have been dating model Kat Torres in 2013.Leo really does have a thing for tall, blonde, models.

Yes, Leo has been rumored to have had a fling with singer Rihanna and there were photos to prove it.

The couple was seen together in both New York City and Paris, making the rumors very convincing.

Lively is now married to actor Ryan Reynolds and has two children. However, we have to say the two did look good together, albeit briefly.

Today Rihanna is linked to other artists such as Drake and was formerly in a relationship with singer Chris Brown. Natalie Denning stated that she had engaged in a fling with Leo upon meeting him in Paris back in 2003.

Whether this is true or not remains to be seen since she may have used his name to get ahead, but she certainly fits the profile.

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