Season 5, Episode 9: Chicago Hope (1995)
Tim and Jill have planned a romantic weekend at a Chicago hotel. But when Tim’s boss Bud asks him to help pitch Tool Time to the manager of a Chicago TV station that same weekend, Tim attempts to juggle both obligations without telling Jill. Tim running back and forth between business meetings in the hotel bar and marital business in their hotel room upstairs manages to piss everybody off - until the Chicago station manager learns what’s going on and encourages Tim to prioritize his relationship with his wife.
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