Herb constantly hits on the station's receptionist, Jennifer Marlowe, and tells every man he meets that he and Jennifer are a couple (a fact he admits to her in the episode "Fire", when the two are trapped in an elevator during a fire). Jennifer finally agrees to go on a date with him in the episode "Put Up or Shut Up", in order to call Herb's bluff; however, Herb is so nervous at even the remotest thought of his fantasies finally coming true that he begins to hyperventilate (an act he repeats in later episodes when under stress), as well as admitting to Jennifer that he feels guilty over the possibility of cheating on his wife. However, there were moments prior to this when Herb showed concern for Jennifer beyond her sexual appeal, such as when he tried to comfort her after a blow-up with her childhood sweetheart (in the episode "I Do, I Do...For Now").