Ally McBeal (1997)

S5E10 One Hundred Tears

Ally takes on the case of a man named Harvey Hall, who broke into his childhood home to leap from his old bedroom window, convinced that he could soar using homemade wings. The homeowner permits him to jump from the roof, and Harvey fulfills his lifelong dream of flying, tragically ending his life in the process. Meanwhile, Harriet Pumple sets out to find dates for Elaine, Coretta, Richard, and John. She pairs Elaine with Victor, who would have ended things if Ally hadn’t intervened. Struggling to find a match for John, the office breaks into song, chanting "we have to get you a woman," leaving John feeling deeply insulted.