The Drew Carey Show (1995)
S07E23 Rich Woman, Poor Man
Episode Overview
Milan sets up her mother, Lindsay, with Drew, hoping she finds someone who appreciates her for more than her wealth. However, when Lindsay takes Drew's car for a spin, she accidentally crashes it into a ditch, stranding them for hours. Surprisingly, Lindsay enjoys Drew's modest lifestyle and expresses a desire to keep seeing him. Just days before her move to Cleveland, she reveals that she would forfeit her hefty alimony if she remarried, raising Drew's concerns. To prove her commitment, he challenges her to live in his world for a week. Lindsay struggles with the changes, developing rashes and losing hair, prompting Drew to confess his feelings. However, she decides to leave, admitting she never had strong feelings for him.
