Will and Carlton begin their first year of college by moving into their own apartment, while Philip and Vivian enjoy their newborn son. Hilary learns that Trevor plans to propose marriage to her during an elaborate stunt on his TV news show.

Will and Carlton begin their first year of college by moving into their own apartment, while Philip and Vivian enjoy their newborn son. Hilary learns that Trevor plans to propose marriage to her during an elaborate stunt on his TV news show.

Registration day finds Will signing up for no-brainer classes, plus one that might truly challenge him - a philosophy course he takes to meet a girl.

Stuck with caring for Nicky for the day, Will soon discovers the benefits of baby-sitting: he's suddenly a big man on campus with the women so long as he poses as a single dad.

A bro with dough? Carlton's upper-class upbringing may make him unwelcome at a black fraternity.

Will breaks a date with Jackie to accompany Hilary to a Playboy Mansion reception for weather reporters being photographed for the magazine.

On academic probation, Will schemes to improve his grades by fixing up a newly divorced English professor with Hilary, who soon finds fault with the man, further jeopardizing Will's academic future.

Will uses booze to prove his manliness while competing with a hulking football hero who wants to score points with Jackie, and his fraternity brothers leave drunken Will in a cemetery, where he is haunted. Meanwhile, Ashley learns that beauty is in the eye of the beholder.