Molly teaches Rick how to be sensitive when he starts dating a new flame, but her efforts backfire when the woman dumps him. Meanwhile, Mary is obsessed with documenting her mother's past.

Mary enters Molly into the town's yearly Quahog Festival Pageant, which Molly doesn't even want to participate in until the teen hears someone insult Mary about her involvement in a previous competition. Meanwhile, Jerry recruits Grant to help him build a float for the festival's parade.

In Part 1 of a two-part episode, Molly develops feelings for her friend Ben and she considers asking him to the prom. Meanwhile, Rick learns that his name is on the deed to the Stage home and he inadvertently loses the property in a card game.