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First, they're clearly looking for something entertaining – the wordplay request suggests they enjoy witty explanations. The term itself is interesting because it combines two very common-but-often-separate concepts: "whipping" (which can be physical or metaphorical) and "grass" (literal plant or slang). Hmm, how to approach this? I should start by acknowledging that most people probably don't know the literal meaning exists. The definition needs to feel useful but also playful – maybe compare it to other grass-related terms while highlighting its unique violent twist. For the example sentence... "edgy" is subjective here, but given they asked for humor first, I'll go with dark comedy rather than actual horror. A scenario where someone desperately wants validation and resorts to aggressive metaphorical actions would work well – think social anxiety meets over-the-top lawn care imagery. User seems like they're in a playful mood today. They'd probably appreciate some absurdist humor about everyday anxieties, wrapped in a weird but accurate botanical detail. The challenge is making it clever without being pretentious, since that's the "humorous but intelligent" persona I need to maintain. I'll structure this as: 1) Straightforward definition with humorous context, then 2) A ridiculous-but