the past, various dates, sexual liaisons, and the like) seem to cross professional ones for Herman on a daily basis. Herman also has a studio apartment located downtown, which, in a first-season episode, is indicated as being a somewhat lengthy subway ride from the Waterton offices. The only other recurring setting is MacAnally's, a restaurant and pub, which presumably is located between Herman's residence and the Waterton offices. It attracts a rather upscale clientele, and it most often sets the stage for Herman's and the other characters' romantic pursuits. The regular real-life characters are as follows: Jay Nichols (Hank Azaria) is Herman's best friend, a resident writer for Waterton who works upstairs. Prior to the timeline of the series, he had helped Herman land a job as a fact checker in the research department. A smooth-talking ladies' man, Jay often is more gutsy when it comes to pursuing women, and typically, is subject to periodic rejection from women who do not tolerate his machismo and clichéd pick-up lines. He is often looked to by Herman as a level of confidence to aspire to, while Jay eventually ponders how Herman's more cautious, "nice guy" persona could work to his advantage. He has also made Herman feel insecure at times because of his position in the company being higher than Herman's. A frequent visitor to the research department, Jay always drops in to have spirited conversation with his best buddy, whom he always calls "Hermo", "The Hermster", or some variation thereof. Originally, Jay is exclusively seen chasing after flashy, status-conscious women, most notably Heddy Newman, who continually turns him down and gives him very little acknowledgement during his visits to the research department. He was engaged to a woman he was hopelessly in love with, but she left him at the altar—which nearly destroyed him. And so he now regards relationships with women as just for sex. His ex-fiancée returns and he falls back in love with her. He prepares to leave all of New York to go away with her, but she abandons him again. Jay pretends he left her this time, but Herman pretends he does not know that she left him. By the third season, Herman fixes up Jay with Louise Fitzer, and the two become an item. They begin to fall in love with each other. Heddy Newman (Jane Sibbett) is a fact checker in the research department