Out of his co-workers at the station, Herb tends to be the closest to Les Nessman. Les and Herb tend to have a love-hate relationship, as Herb routinely insults and derides Les. At one point, a jealous Herb tried to have Les' date with Jennifer for an awards banquet broken by manipulating Mr. Carlson, and at another time even goosed Les' mother, thinking she was Les in drag (as they strongly resembled each other), only to be confronted by an infuriated Les moments afterward. In turn, Les seriously injured Herb when pulling him along on a hang glider for a promotional stunt (Les had stopped at a stoplight, causing the glider to plummet to the ground). One time Herb actually loaned Les his speed boat only for Les describe to Herb about how the trailer hitch came apart..and sent the boat going down the highway; Les is so oblivious that he doesn't realize that the loss of his boat causes Herb anguish! However, Les and Herb have also shown signs of strong friendship. When Herb's wife threw him out, Les pleaded Herb's case to the others at the station so he could have a place to stay. In the episode "Les on a Ledge", when Les was considering suicide (due to rumors that he was homosexual) by jumping off a ledge outside Mr. Carlson's office, Herb eventually went out on the ledge himself to get Les to come back in (and ended up falling onto the firemen's nets several stories below, incurring yet another serious injury). Les summed up their relationship by saying "I hate him, but he "is" my best friend."