Don: Congratulations, Dick, you got yourself a hell of a rhymer. I mean, I've tried to rhyme, you know. There was a dog who sat on a log, his name was...Rog? That sorta thing. Hold on to her, Dick. She's one of a kind.
Dick: So you like the the rhyming, eh? You like the rhyming?
Don: Yeah.
Dick: And what if the rhyming were never to stop? On, on, and on till your head doth pop. Oh, look! A book! A book on schnook! What kind of crook took my schnook nook book? Perchance, methinks, thee, hither, yon, thou. I think I'm going to have a freakin' cow!
Don: You sure seem to hate her, sounds really tough.
Dick: Hate is a strong word, but not strong enough.
Dick: You have a little tofu on your lip.
Jennifer: This smoothie is delicious. Please have a sip.
Dick: Ah, thank you. But, no, just uh, please, go like this [makes wiping motion near his mouth].
Jennifer: I've got an idea, how 'bout we kiss?
Dick: Okay, time out, you're missing my point.
Jennifer: Finish your food and we'll blow this joint.
Dick: Just listen to me, you have tofu on your lip. It's been there for what seems like an eternity, now please just flick it the hell off your face! [She despondently wipes her face.] Thank you, that's better. Now we can embrace.
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