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

Enrolled at the newly coed Bel-Air Prep, Ashley begins dressing to entice guys, using Will's preferences in women as her examples.

While Philip entertains rude, senile Judge Robertson, Will accepts expensive gifts from Lindsey Simon, a rich classmate who wants to buy his affection.

At Vivian's Lamaze class, Will cozies up to a pregnant sportswriter, who takes him to a game - and delivers more than just fun.

Geoffrey humiliates himself by insulting the Banks family and quitting his job when Will and Carlton trick him into thinking he has won millions of dollars in the lottery.

When Monique refuses to have sex until she's married, Will stages a mock wedding ceremony with D.J. Jazzy Jeff as the preacher.