Jeffrey A. Townes

At Uncle Philip's insistence, Will joins his prep school's poetry club, and he enlists Geoffrey's help when he must present a poet for a reading.

Will returns from spending the summer in Philadelphia with a new look that doesn't sit well with Uncle Phil.

After Hilary appears in traffic court, part of her sentence includes several hours of community service at the Southside Free Clinic, where she meets handsome doctor Alec Hudson. Meanwhile, Jazz becomes a butler.

Will has girl problems after a date with Jazz's domineering sister, who's ready to pick out a china pattern before the night is over.

Will buys a used car and promptly crashes into a law student's vehicle.

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