The Drew Carey Show (1995) : 4x12

Drew decides to take night school classes to pursue a master's degree after a young man he was mentoring suddenly receives an executive position at Winfred-Louder. When his statistics professor recommends that the students find study partners, Drew pairs with Celia, a 62-year-old woman who is the only other ""old person"" in the class. They have a good time hanging out at Drew's house after a study session, and soon realize that they are attracted to each other. Celia stays the night, although they do not have sex. Drew's friends mock him after learning of the age difference, but he insists that he really likes Celia. He is puzzled when Celia ignores him in class and says that she doesn't want to see him anymore. Drew shows up at her favorite bingo parlor, and Celia explains that she dumped him because she thought he would eventually become embarrassed by her. Drew proves himself by taking over for the bingo caller and publicly announcing his feelings. Celia agrees to date him.