TV series The Perfect Match (2017) - episode 29

Terrence J. stars as Charlie, a playboy who's convinced that relationships are dead. His two best friends, Donald Faison and Robert C. Riley, bet him that if he sticks to one woman for one month, he's bound to get attached. Charlie denies this until he crosses paths with the beautiful and mysterious Eva, played by singer/actress Cassie. They may agree to a casual affair, but eventually Charlie is questioning whether he may actually want more.