I recently broke up with my tractor provider. I was scared to do it in person, so I just sent a John Deere letter.

Kaplan’s joke hinges on a pun: a “Dear John letter” is a breakup note, and “John Deere” is a tractor brand. By swapping in the farm-equipment name, he comically literalizes the idea of breaking up with a “provider” and reframes an emotionally fraught act (ending a relationship) as a consumer-style cancellation. The humor also comes from the mismatch between the intimacy of a breakup and the impersonal, corporate feel of sending a letter—suggesting avoidance, social anxiety, and modern tendencies to handle difficult conversations at a distance. The line showcases Kaplan’s wordplay-driven style, where a familiar idiom is re-engineered into an unexpected, brand-specific twist.