Spencer seeks Dee Dee's advice to land a sophisticated woman, and again turns to Dee Dee for help ridding himself of the woman when she proves to be unbearably controlling. Gabrielle repeatedly refuses Spencer's efforts to break up with her. Meanwhile, Mona reluctantly gives Phyllis some advice before her first big romantic weekend with Glen. Dee Dee plans a bachelor party for a client.

After Dee Dee complains about Brett's sexist treatment of her, Charles and Spencer show up at the office to confront him. Their actions backfire, as everyone at the office begins thinking of Dee Dee as a "daddy's girl." Dee Dee, with encouragement from Mona, Phyllis and Big Dee Dee, sets out to prove herself by trying to land a successful athlete who has refused to sign with any agent.