Princess Carolyn's agency merges with that of her rival Vanessa Gekko, who takes her office and her client. She tries to get BoJack to do a bourbon commercial, but he is more interested in romantically pursuing her, forcing her to get Todd to do it. After Gekko one-ups her multiple times, she finally succumbs to BoJack's advances and goes on a date with him, only for him to get a foreboding call back from Herb and abandon the date, hurting her. She formulates a plot to lure her former client away from Gekko's project, getting Gekko fired and giving her her office back. She gives a director the idea to make a movie about the Hollywood Sign and convinces him to hire BoJack, only to get a forlorn call from BoJack as he returns from Herb's house. As Princess Carolyn looks out the window at a billboard of Todd being put up, her phone wishes her a happy fortieth birthday.