Liz gets a surprising phone call from her father, who's planning a trip to New York, without Liz's mother. He begs Liz to not tell her mother about his trip. Liz remains confused by the phone call and goes to Jack to for advice.
Avery wants Jack to set up boundaries with Liz, which means no more acting as her mentor. Jack's forced to tell Liz he can't help with her latest issues with her father. A puzzled Liz leaves Jack's office, and Jack proceeds to search for a new mentee. He looks at Jonathan, but believes his assistant is too weak for the role.
Dick shows up at his daughter's apartment missing his glasses and wearing an Ed Hardy shirt. Liz immediately tells her father to go back home to her mom and work things out. Dick tells her that after 45 years of marriage, he and Liz's mother don't laugh anymore. Liz wants Dick to suffer through his "gentlemen's intermission" somewhere else, and asks him to leave.
Cerie tells Liz that when old guys hit on her, she brings up their daughters, which usually creeps them out. This gives Liz an idea. She dresses up and heads to the bar where she knows her father and his old Army buddy Gary are going. With Dick's poor eyesight, he has no idea the woman next to him is really Liz!
After Gary tries to hit on Liz, she reveals her true identity. Dick tells Liz that her plan just makes her look crazy. He grabs Gary and heads to a fun bar a few blocks away with pretty rainbow flags outside of it. Liz remains frustrated with her father's attitude.
After Jack confesses to Avery that he can't find anybody worthy enough for him to mentor, Avery allows him to continue his mentoring relationship with Liz. Now Jack can help out with her Dick's "gentlemen's intermission." When Jack calls Dick to threaten him, Dick immediately tells him he's heading back home to Philadelphia and his wife.