Expecting Amy

S03E02 Tony's Sister and Jim

After her divorce, Monica, Tony's sister, is back in New York, and Tony hopes to spark a romance by setting her up on a date with Alex. However, while waiting for Alex in the garage, Monica strikes up a conversation with Jim, and they instantly hit it off, leading to a budding romance. Tony disapproves of their relationship and urges Jim to stay away from her. When Tony unexpectedly finds Jim at Monica's apartment during a visit, he is furious and ready to throw Jim out. Monica stands up to Tony, calling out his childish behavior and attempts to control her life. Realizing his mistake, Tony apologizes and comes to terms with their relationship.