Duncan's friends replace him with Kimberly in their online video game tournament, so he joins the opposition to betray them and humiliate Kimberly. Meanwhile, Annie tries to force Jack to throw out all his old memorabilia cluttering the garage.

The town celebrates its annual Witch Day, which involves pronouncing a mortified Duncan the "town virgin" for the big ceremony, but he protests the celebration to impress Mia, who finds it sexist and barbaric. Meanwhile, Annie and Jack steal a dead woman's chili recipe to try and win the celebration's chili cook-off.