S7·E23 Rich Woman, Poor Man

Milan fixes up Drew with her mother, Lindsay, because she wants her to finally meet someone who isn't just after her money. Drew makes the mistake of allowing Lindsay to drive his car, and they are trapped for several hours after she crashes into a ditch. Lindsay finds Drew's lifestyle charming, and wants to continue seeing him. She is scheduled to leave town a few days later, but suddenly announces that she is moving to Cleveland. Drew is alarmed to learn that Lindsay would lose her $500,000 per month alimony if she ever re-married. He predicts that she will soon grow tired of the novelty of living like a poor person. He challenges her to spend one week in his world. She tries her best to adjust to a simple lifestyle, but really doesn't take to it. She begins breaking out in rashes and losing her hair. Drew decides that he is in love with Lindsay for some reason. After he tells her this, she announces that she is leaving. She never really liked him that much, and cannot sur