Grace contemplates having an affair with a married man. Elsewhere, Jack begins new career as a host of his new talk show "Jack Talk." Will gets some advice from Malcolm and tries to hide from Karen the fact that Stan is alive.

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.