Judith calls Dag after Camilla says that she doesn't want to go to her prom, because the Secret Service will be there. Since Camilla really wants to go with her new date, Jeremy, Dag compromises by offering her minimum visibility protection. In assigning positions, Sullivan becomes chaperone, and Cole, an undercover high school student. Judith arranges for Sullivan to hook up with a former prom date that could've been, Patti, only to find out while he's chaperoning what a menace she's become. Meanwhile, a heavily made-up Cole makes another attendee jealous when her boyfriend develops a wandering eye pointed squarely in Cole's direction. Judith defies Dag's orders and tags along with him to listen to things from the monitoring van. Judith's family stories cause Dag to blow up, claiming he doesn't care to know them if it doesn't involve his job. Dag proves he does care by saving the day after Jeremy is caught on the microphones saying that he's using Camilla to get a good tabloid story.

With Valentine's Day approaching, Dag hopes to get back in the saddle after becoming hot under the collar for Judith's fiery temp secretary, Gina Marie. Trouble is, Agent Morton's got his eye on her, too. When the pair find themselves competing for Gina's attention, they make a deal that neither will go out with her to preserve their friendship -- a deal neither keeps. Also, Judith wishes to learn how to fire a handgun and enlists the aid of Agent Cole, while Sullivan seeks help from Agent Pillows to discover who his secret admirer is. Judith's attempts at shooting are a disaster, after which she confesses to Dag why she wanted to learn in the first place.