Having quit his job at the law firm, Will turns to a career in writing where he catches the eye of Malcolm, who claims to have high-profile connections -- but when his writing career fails, Malcolm has another job offer for Will. Meanwhile, Tom, an old flame from college, returns to ask Grace to design a hotel that he and his wife just bought -- only to discover that there are still romantic feelings between the two of them. Jack struggles to produce his latest show for OutTV, but spoiled child star Randall fails to embody Jack's vision. Under threat of a lawsuit, Karen is forced to publicly apologize to Beverly for an embarrassing rumor.

After his first day, Will becomes suspicious of his new job -- especially when he finds himself in an empty office with no co-workers, a German shepherd and a Russian-speaking thug.

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 how to swim, Jack insists that he teach Will how. Meanwhile, Karen sets Grace up on a blind date with one of Malcolm’s friends.

Karen is finally forced to come to terms with her feelings for her presumed-dead husband when Jack surprisingly tells her he thinks she belongs with Stanley, not Malcolm.

The day before Will’s 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.