Jimmy encourages an ambivalent Paul to accept a career achievement award. Sean approaches Liz with a business proposal.

As Brian’s wedding approaches, Alice takes issue with how Jimmy is living his life. Liz learns a secret.

While trying to stay out of Alice’s business, Jimmy has to “Jimmy” an insecure Brian. Gaby leans on Paul for advice after her sister drops a bomb.

Jimmy, a therapist mourning his wife, takes a more proactive approach with his patients in the hopes that helping them will help himself.

Jimmy grapples with his guilt over Grace. Paul makes a decision about his relationship. Liz tries to help Gaby find balance in her busy life.