It starts with Rihanna, like any good story should. Cuttler, who was there, says Port approached the singer at a nightclub, and the two gushed over each other's respective projects. Then, apparently, in walks Leo, insinuating that he, himself, is a fan of The City. The night progresses and while nothing happens between Port and DiCaprio, they do exchange numbers, and remained in contact via BBM (tbt) for around six months, according to the host.