Jazz asks Will the favor of taking his sister Janet out on a date after she moves into town. Will does so reluctantly, until Jazz introduces the two. Will takes Janet on a date, but learns that she's extremely bossy and has her whole life planned out for the pair already. Janet tells Will what to do, where to go and how to look, and criticizes Will for every little thing. Jazz recommends that if Will doesn't like her he should introduce her to someone else. He does so to Carlton at a club. When Janet displays her rudeness, Carlton sternly tells her he expects his dates to be courteous and respectful to others, which surprisingly causes her and Carlton to become a nice couple.

One of Vivian's students, Kayla Samuels comes over for dinner and Will tries to impress her but fails. Eventually, Will wins her over and inadvertently starts taking time away from her studies so Vivian tells him to cut back on their relationship so Kayla can have a good future. Vivian winds up lecturing Kayla and revealing things about her own struggles to be successful.