SNL: Issa Rae Almost Breaks Character During the World's Most Awkward First Date

If there's one thing that Issa Rae knows, it's awkward romances. On Saturday Night Live's Oct. 17 episode, the Insecure creator went on a first date where she and her beau, Chris Redd, were repeatedly interrupted by Rae's exes. We would never judge anyone's romantic taste, but it's obvious that working as Time Square's first-ever Black Elsa doesn't offer the best dating prospects. From the guy who sells roses on the corner to Karate Man and the silver robot, Sharon (Rae) has definitely had a bit of a checkered romantic past. If Rae almost breaking into laughter at Pete Davidson's Karate Man doesn't get you, then Bowen Yang's parting line calling her "Sugar Foot" probably will. Watch the sketch above.