When Jack learns that Will never learned to swim, Jack insists that he teach Will how. Meanwhile, Karen sets Grace up on a blind date with one of Malcolms friends, but Grace can't stand him or his penchant for bad poetry during their seemingly never-ending nine-course dinner.

The day before Will's (Eric McCormack) charity auction and carnival, Jack meets and begins dating Baby Glenn, who is still riding his fifteen minutes of fame from when he got trapped in a hole for three days in the eighties. The two "celebrities" agree to be auctioned off for charity - Baby Glenn's fans spend over a thousand dollars, but Jack begins to question his own notoriety when no one bids on him. Meanwhile, Karen just can't force herself to break up with Malcolm, so to soften the blow she recruits Grace to be his date to the carnival. But Grace can't stand his weird quirks and clingy personality and finally makes Karen confront him.