Will wants to go out with a beautiful girl he meets at the country club, but first he must figure out how to impress her extremely snobbish and very protective father so he seeks tips from cousin Carlton on becoming preppie.

Will gets a visit from an old pal named Ice Tray, who, to Vivian and Philip's dismay, warms up to Hilary.

Will challenges Carlton to spend time in a tough neighborhood, trying to survive by masquerading as a financial consultant.

R&B singer Tevin Campbell plays teen idol Little T, who surprises Ashley on her birthday with a special song and an invitation for a date.