Season 6, Episode 16: A Funny Valentine (1997)
Tim receives an invitation to meet with Liddy Talbot, a lounge singer who was the mother of one of his high school classmates. At a hotel bar where she’s singing, Liddy explains that she and Tim’s father dated before he met Tim’s mother. Liddy alludes to the fact that she and Tim’s father remained close after they broke up. Tim grows worried that his father had an affair with Liddy and he flees the meeting before he can learn anything else, not wanting to compromise his memories of his father as a decent man. After a chat with Wilson, Tim decides he needs to know the truth about his father no matter what and returns to the hotel. Liddy tells Tim that she and his father were nothing more than friends after they broke up, and that he loaned her money to buy her first piano - a debt that she now wants to repay to Tim.
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