Unhappily Ever After (1995)

Season 1: Episode 9

Jennifer is depressed because she can't get a date, and wants to be lusted after. When Jack takes the rest of his stuff out her basement, she decides to fix up the house. She hires Matt, a twenty year old who just moved into Jack's building, who was captain of the football, baseball, and basketball teams in high school. When Jack tells Jennifer that Matt has a habit of sleeping with the women he works for, Jennifer goes after him. Tiffany gets really aroused by him, and Jennifer forces her to stay away from him so that she won't have to compete. After Matt shows no interest in her, and runs off with Mrs. Wilson, who has a big butt and four chins, Jennifer complains to Jack that she isn't attractive.