At the supermarket Jack and Dante tease Will about his attraction to the 20-year-old checkout clerk Tina, but both men encourage him to ask her out. Meanwhile at home Nicole is asking Carly if it would be all right for her to go out with Preston, Sarah's 22-year-old trumpet instructor. Carly says Jack would never allow it. When the men return telling the story of Will's crush on Tina, Nicole angrily demands to know why it's OK for Will to date an older person, but not her. Carly, disdainful of Jack's double standard, sides with Nicole. Trapped by his hypocrisy, Jack declares that if Will gets a date with Tina, Nicole can go out with Preston. Jack thinks he's safe with this solution, but Tina promptly accepts Will's invitation to go out.