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)
Dick's Big Giant Headache (1) - S4-E23
Trivia: When the Solomons meet the Big Giant Head at the airport and ask how his flight was, he says that it was horrible because when he looked out the airplane window, he saw something on the wing of the plane. Dick responds that the same thing happened to him. William Shatner appeared in the 1960's Twilight Zone episode "Nightmare at 20,000 Feet" in which a gremlin tried to destroy the wing of a plane. John Lithgow appeared in "Twilight Zone: The Movie" playing the same character in the same situation.
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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