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08:32 on May 25 2016

Rihanna, Leo DiCaprio, Nina Agdal -- Three's a Charm? (PHOTO)

TMZ — Leonardo DiCaprio had either the best night of his life or a super awkward encounter with former GF Rihanna and new rumored fling Nina Agdal ... both under the same roo... more info

Rihanna

19:05 on May 25 2016

Leonardo DiCaprio Parties at N.Y.C. Nightclub with Rihanna and Model Nina Agdal

People.com — The actor arrived at the club with Agdal and a group of friends, while Rihanna showed up solo more info

Rihanna

18:41 on May 26 2016

Leonardo DiCaprio Is All Smiles Following His Night Out With Rihanna

PopSugar — One day after his night out with Rihanna at the Up&Down nightclub in New York City on Tuesday, Leonardo DiCaprio was spotted cycling around town with a couple of friends.... more info

Rihanna