A sketch about a boy and a girl that like each other, and give tips on how to be "the perfect couple". Heather Darling (Lisa Foiles) is the head cheerleader and Brad Dashman (Jack DeSena) is a jock and her boyfriend. Heather and Brad would often make weird kissing noises in between the discussion. At the end of the sketch, they would argue. Heather would then yell "INCOMING", and beat up Brad. Shane Lyons occasionally appeared as Cupid.

In Season 10, when Shane departed, the role was taken over by Denzel Whitaker (this replacement was mentioned by Denzel as Cupid when he told off Brad and Heather: "I've been stuck, listening to your stupid arguments and your weird kissing noises! I don't like it, and I didn't like it two years ago when I was a tall, white guy!"). In another episode, when Cupid fussed at Brad and Heather and treated them like jerks and morons, Brad and Heather yelled "INCOMING", and beat up Cupid.