The Drew Carey Show (1995)

S3E5 A Very, Very, Very Fine House

Following Larry's mischief in the last episode, the government confiscates Drew's home, intending to auction it off. Inspired by Nicki, Drew decides to file for bankruptcy on the property to relieve his financial burden, and enlists Lewis to bid for him at the auction. Meanwhile, Drew struggles with the reality of Kate and Oswald's relationship, leading to heightened emotions and conflict as he grapples with their new romantic connection.