Just as Dean prepares to give up on what he thinks is a hopeless search for love, he is reunited with Gail (guest star Christina Applegate), an old flame who restores his belief in romance. Meanwhile, Deb encourages Stewart to change his strict ways and let Lizzie have a supervised date with Joel Zadak.

Stewart convinces Dean he can't keep using his celebrity if he really wants to be a "regular guy." But when the brothers find themselves in serious trouble, Dean's fame might be the only way to bail them out.