Will hits it off with the full-figured Dee Dee, but her size keeps him from asking her to the dance.

After winning at the country club's Monte Carlo night fund-raiser, Will learns that he's expected to donate the money to charity.

Hilary must work for a caterer after her credit cards are cancelled.

Needing a game show partner, Will must choose between bickering friends.

Will dislikes his mother's new boyfriend.

Ashley cringes when the family oohs and aahs over her relationship with Kevin , but Will chokes when she asks him about sex - and her curiosity about reproduction sends Will to a pregnancy counseling center.

Will and Carlton lose their shirts investing on a tip - then take jobs as strippers to recoup their losses and get Vivian's bracelet out of hock.