S5·E10 One Hundred Tears

Ally defends a man who broke into his old house to jump out of his old bedroom window. Harvey Hall believes he can fly using wings he made himself. The house owner allows him to jump from the roof, and Harvey accomplishes his life long dream of flying, at the cost of his own life. Meanwhile, Harriet Pumple tries to find a match for Elaine, Coretta, Richard and John. She matches Elaine with Victor, who would have dumped her if it wasn't for Ally asking him not to. But Harriet can't find a match for John, so the entire office sings "we have to get you a woman" for him. John is profoundly insulted.