ENTERTAIN THISDrake and Rihanna through the yearsNEW YORK, NY - AUGUST 28: Singer Rihanna (L) and rapper Drake pose onstage during the 2016 MTV Video Music Awards at Madison Square Garden on August 28, 2016 in New York City. (Photo by Kevin Mazur/WireImage) ORG XMIT: 659513285 ORIG FILE ID: 597579536Kevin Mazur, WireImageNEW YORK, NY - AUGUST 28: Drake presents Rihanna with the The Video Vanguard Award during the 2016 MTV Video Music Awards at Madison Square Garden on August 28, 2016 in New York City. (Photo by Michael Loccisano/Getty Images) ORG XMIT: 659513207 ORIG FILE ID: 597576074Michael Loccisano, Getty ImagesNEW YORK, NY - AUGUST 28: Drake presents Rihanna with the The Video Vanguard Award during the 2016 MTV Video Music Awards at Madison Square Garden on August 28, 2016 in New York City. (Photo by Michael Loccisano/Getty Images) ORG XMIT: 659513207 ORIG FILE ID: 597616122Michael Loccisano, Getty ImagesNEW YORK, NY - AUGUST 28: Drake presents Rihanna with the The Video Vanguard Award during the 2016 MTV Video Music Awards at Madison Square Garden on August 28, 2016 in New York City. (Photo by Michael Loccisano/Getty Images) ORG XMIT: 659513207 ORIG FILE ID: 597576062Michael Loccisano, Getty ImagesLONDON, ENGLAND - FEBRUARY 24: Rihanna performs on stage at the BRIT Awards 2016 at The O2 Arena on February 24, 2016 in London, England. (Photo by Ian Gavan/Getty Images) ORG XMIT: 606687817 ORIG FILE ID: 512081044Ian Gavan, Getty ImagesLONDON, ENGLAND - FEBRUARY 24: Rihanna and Drake perform on stage at the BRIT Awards 2016 at The O2 Arena on February 24, 2016 in London, England. (Photo by Karwai Tang/WireImage) ORG XMIT: 606687899 ORIG FILE ID: 512135828Karwai Tang, WireImageORG XMIT: RH 39783 2011 GRAMMYS 2/11/2011 2/13/11 8:01:05 PM -- Los Angeles, CA, U.S.A -- Rihanna and Drake performs at the 2011 Grammy Awards.-- Photo by Robert Hanashiro, USA TODAY Staff (Via OlyDrop)Robert Hanashiro, USA TODAYORG XMIT: RH 39783 2011 GRAMMYS 2/11/2011 2/13/11 8:01:41 PM -- Los Angeles, CA, U.S.A -- Rihanna and Drake performs at the 2011 Grammy Awards.-- Photo by Robert Hanashiro, USA TODAY Staff (Via OlyDrop)Robert Hanashiro, USATLOS ANGELES, CA - FEBRUARY 13: Singers Drake (L) and Rihanna perform onstage during The 53rd Annual GRAMMY Awards held at Staples Center on February 13, 2011 in Los Angeles, California. (Photo by Kevin Winter/Getty Images) ORG XMIT: 108805628 [Via MerlinFTP Drop]Kevin Winter, Getty ImagesORG XMIT: RH 39583 NBA All Star 2/19/2011 2/20/11 7:55:39 -- Los Angeles, CA, U.S.A --Rihanna performs with Drake during the 2011 NBA All Star Game at Staples Center in Los Angeles, CA -- Photo by Robert Hanashiro, USA TODAY Staff (Via OlyDrop)Robert Hanashiro, USATLOS ANGELES, CA - FEBRUARY 20: Rihanna and Drake perform during halftime of the game between the Eastern Conference All-Stars and the Western Conference All-Stars in the 2011 NBA All-Star Game at Staples Center on February 20, 2011 in Los Angeles, California. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. Mandatory Copyright Notice: Copyright 2011 NBAE (Photo by Noah Graham/NBAE via Getty Images) ORG XMIT: 109272881,109009675 [Via MerlinFTP Drop]Noah Graham, NBAE/Getty ImagesThe two hung out at a party in 2010, too.Johnny Nunez, WireImage