The Last Temptation of Chuck

Deciding Chuck has had enough time to grieve over Nora's death, Pop gallantly sets him up on a blind date. Since Chuck doesn't have the backbone to do so, Kit tells Pop that he has no right to play matchmaker for his son, especially since Chuck is too shy to be fixed up. Despite Kit's protests and Chuck's desire to remain a one-woman guy, Chuck ends up going through with the affair... albeit with a toupee. Although his date, Bonnie, is better-looking than he is, and a good ten years younger, the two of them have a couple things in common -- her mother fixed her up, and she's no more confident on the dating scene than he is. But he comes home from their dinner date feeling like he did everything wrong, starting with his failing to admit to her that he's balding. When Pop apologizes to Chuck for meddling, claiming that he didn't want to see him end up alone like he is, Chuck nervously sees Bonnie a second time, sans the hairpiece -- after which he learns that she knew all along, and like

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S02E12 - The Cavanaugh Curse