Harriette's troubled cousin, Clarence, comes to live with the Winslows until he can straighten out. Instead of deciding to fly right, Clarence becomes a bad influence on Eddie and gets him and Urkel into big trouble when they are caught with a bunch of pretty girls ... and a stolen car! Eddie confesses and realizes he shouldn't have listened to Clarence, whom Harriette quickly becomes fed up with and kicks out of the house.

Urkel, Eddie and Waldo go on the teen dating show "Dudes," which Laura insists is raunchy and sexist. Urkel easily wins a date with one of the female contestants, but instead uses his live TV opportunity to reaffirm his love for Laura.

Eddie becomes despondent when he learns that Oneshia is two-timing him. At a high-rise party, he goes onto the fire escape to sort his emotions out ... and considers suicide. Urkel and Waldo, concerned for their friend, try to talk Eddie down, but all three of their lives are soon endangered when the fire escape begins to give way. Meanwhile, Fletcher Thomas proposes to Estelle, and her answer upsets Carl.

Urkel hosts three Valentine's Day stories. In "True Love," Eddie sings a song to clear up Greta's misunderstandings with his high-school ex-girlfriend Oneisha. "First Love" involves Richie and 3J vying for the affections of Kelsey Webster, Maxine's niece,when Richie decides to drop out, Kelsey decides that he's the better man. In "Lasting Love," Harriette accuses Carl of being cheap in buying her the same gifts every year and he enlists Richie and 3J to help him make up for it. Finally, Urkel gets his own Valentine's Day gift in the form of Myra dressed as a polka-costume-clad Cupid.

Eddie takes his pranks on Laura too far by inviting her ex-boyfriends over to the house whenever Stefan is around. Laura decides to fight fire with fire by conning Steve into helping her get even with her dim-witted brother. She uses his black book, which contains phone numbers of Eddie's previous girlfriends, and invites them over on his birthday. When he and Greta arrive to his birthday party to see his ex-girlfriends, they are incensed by the whole thing. Finally, Steve sets both Eddie and Laura straight on how ungrateful they were to have each other. Steve admits that he was always jealous of them because his parents never loved him and that the Winslows were like his own family. Both siblings apologize soon after. Meanwhile, Commissioner Geiss learns a lesson that sometimes it's better if a more experienced cop, like Carl, is promoted to captain over an inexperienced cop, like his son.