Hugo, the loathsome health inspector who torments Bob, quits his job to become a nudist after discovering the town's new nude beach. His replacement, Tommy (guest voice Fred Armisen), seems nice enough until he blackmails the Belchers into letting him perform his terrible music at the restaurant, which drives all the customers away. Unable to tolerate it anymore, Bob decides upon the lesser of two evils and braves the nude beach (and bares.. well, everything else) to find Hugo and bring him back.

When a heart-shaped pancake simply doesn't cut it, the kids convince Bob to let them skip school in order to help him find a Valentine's Day gift that will "wow" Linda. Meanwhile, in the spirit of the romantic holiday, Linda sets up a speed-dating event at the restaurant that doesn't go exactly as planned.