The Drew Carey Show (1995)

S5E4 Drew's Reunion

As the group gears up for their high school reunion, Kate is eager to reconnect with Patrick, her once-geeky classmate who has now become a successful tech entrepreneur. Lewis hilariously poses as Bo Derek's chauffeur at the airport and unexpectedly secures her as his date for the evening, under the condition that he refrains from physical contact. Oswald reunites with his former barber shop quartet. During the event, Drew faces embarrassment when the speaker highlights his single status, unchanged job, and living situation with his parents. He's taken aback when Kelly, the former head cheerleader, suddenly shows interest in him. Bo Derek suggests that Drew's appeal lies in his kindness and stability. After Patrick arrives late, Drew invites everyone to his place for drinks, hoping to give Kate more time with him. Meanwhile, an attractive woman seeks revenge on Oswald for past insults and their brief encounter. Drew uncovers that Kelly's life is far from perfect.