Episode #318 "Portrait of Tommy as an Old Man"

An obsessed Don steals a pair of Sally's underpants while she's folding laundry; later, feeling guilty, he unsuccessfully tries to return them. When Dick orders Tommy to go observe a rave, Tommy says he's too old for this crap; he's retiring from the mission effective immediately. Dick assigns Tommy's information officer job to Harry. Mary's teaching job is sucking her dry; at Dick's insistence Mary confides that her childhood dream was to be a torch singer. Dick is instantly determined to make Mary's dream come true; he gives Harry an assignment to find a venue for Mary's debut. Tommy, enjoying his "retirement," has begun playing Scrabble in the park with several elderly men; he likes his new life so well that he takes up residence at a retirement village. Dick and Mary go to dinner at the Stonehouse, where Harry has booked a singing gig for Mary; Dick anticipates giving Mary the thrill of her life, but when she's introduced as the evening's entertainment, she walks out of the restaurant. Don, terrified at what Sally's reaction will be, confesses to the theft of her underpants, but Sally, to Don's amazement, thinks that he's sweet and gives him her bra so he'll have a matching set. Back at the office, Dick persuades Mary to sing for him; he tells her she was wise to become a teacher. And Tommy decides that retirement "makes you old" and wants his job back.