Martin convinces Toby to marry Gibby so that he can get his green card, but becomes annoyed when the wedding plans disrupt her work.

Ellen, a beautiful writer of Martin's, asks him to her apartment, with an unusual request that he conceive a child with her. After talking it over with Jude, he accepts under the impression that he'll get to make love to her, but she only wants him to donate semen.

Martin finds his bar mitzvah bonds in a closet and suddenly has extra cash. Toby encourages him to invest $5,000 in a fledgling business she is setting up offering stock tips over the phone, 555-TIPS. The business goes terribly, until a wrong number mistakes it for an S&M phone-sex chat line and stays on for hours. Seeing where the real money is, Toby employs the services of her family – Gina, Angie – in order to cover the phones.

Martin and Judith take a pre-Xmas drive and get stranded in a barn, Eddie is stood up by a girlfriend and spends Xmas in a bar with Santa Claus, Toby wants to become a nun and Jeremy's special Xmas present from his girlfriend doesn't quite go according to plan.

Martin is blinded in a bizarre accident.

Under pressure from Gibby to get an elite writer, Martin attempts to lure the writer dating Toby (who coincidentally, is an award-winning author).

Martin's friend likes Toby.