Continuity mistake: When Jennifer comes into work the next day after her dinner date with Dick, her face is covered in hives from an allergic reaction. Later when Dick interrupts her choral group, the hives on her face have disappeared. She and Dick are wearing the same clothes in both scenes, so she couldn't have overcome such a reaction in such a short amount of time. (00:12:30 - 00:15:00)
Trivia: Dick is never seen walking in this episode and is only in an upright position when he moves from the chair in the lounge room to the wheelchair in the opening scene. This is because John Lithgow hurt his ankle playing tennis, and the episode was written to allow him to be in a wheelchair for the entire episode.
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Answer: The writers often have Dick respond to Mary with a retort that he thinks is in the common vernacular but makes a mistake in wording that is often funny. Dick seems to be imputing a criticism from Mary and responds with a corruption of the more common "I'm going to wear your ass like a hat!" I doubt it has anything to do with owing taxes. Probably just one of the writers assuming a common regional phrase would be universally recognized.
That makes total sense. I always interpreted it as perhaps snowshoes are an expensive item, and given that he was blaming Mary for his newfound financial woes, he was equating her living off his generosity and used snowshoeing as a metaphor.
Phaneron