Rihanna-Leonardo DiCaprio Dating Rumors: Both Spotted At Drake’s Private Party In New York City

Rihanna and Leonardo DiCaprio were spotted together on Wednesday night, fueling romance rumors that surfaced earlier this year. The two attended the singer’s former boyfriend Drake’s private party that continued until Thursday morning in New York City.

Rihanna and DiCaprio were pictured at the party, which was also attended by actor Bradley Cooper and model Tyson Beckford, according to reports. The “Diamond” hitmaker was seen wearing a casual outfit, while “The Wolf of Wall Street” star reportedly tried to hide his face from the paparazzi.

"They were whispering and staring into each other's eyes,” an eyewitness said, according to Us Weekly. The 27-year-old singer and the 40-year-old actor were first seen together at a villa in Los Angeles in May 2009, according to Mirror Online. Later in 2011, they were seen flirting at the Coachella Valley Music & Arts Festival in Indio, California.

The dating rumors began after the two attended a Playboy Mansion party together in January. The Oscar-nominee also threw a birthday party for Rihanna in February. At that time, Chris Brown, who had previously dated Rihanna, spoke about the singer's rumored relationship with DiCaprio, saying that she upgraded by moving on with the Hollywood A-lister.

In March, Rihanna reportedly denied dating DiCaprio, explaining: “I'm so busy right now that I just don't have a lot of time to offer to a man so it wouldn't even be fair to be thinking of pulling somebody else into this life. But if I did, he would have to be man enough to live with my schedule and not get scared."