Halloween at the diner finds Michael (Michael Landes) trying to prove he can be shallow when it comes to his sex life, and Gaby wanting to be open-minded about a guy she meets who fancies women's clothes.

Rhea Perlman guest stars as a bookie's widow looking to collect a debt from Jack (Jim Pirri); Gaby is sexually harassed at her temp job and Michael wants her to sue.

Jack introduces budding filmmaker Russell (David Krumholtz) to his prison buddy's girlfriend; Albie thinks Gaby is after his job.