The Best DMs Sound Like...
"Tell me how you'd like to accomplish that plan, and I'll see if there's an appropriate check you can take."
"Oh, well, I think you actually ran out of arrows in the last combat, but I'll let you roll this one just for fun. Dexterity seems to be the most appropriate. If you roll high enough, I might look past it and let you substitute the shaft with something else on-hand."
"Ah, a Dirty 20, in more ways than one..."
"Well, before I answer that, roll a Persuasion or Intimidation check to see if he responds the way you'd like him to. I'll leave it up to you which one."
"Without needing to roll an Insight check, I can tell you that he doesn't seem to immediately hate it, and you get the impression that he secretly kind of likes it. But to everyone else, he's trying to keep a straight face, if you catch my drift."
"He whimpers, 'I thought you ran out of arrows...' How do you respond?"
"'Oh,' his eyes widen. 'Then what's...'"
"Very rad idea, but I don't know that particular rule--something like that might require an Initiative roll. Let me look it up quick."
"Hey, has anyone seen my PHB? Hmm...maybe it's in my room..."
"Mom? Mr. Drake?"
"No thanks, I'd love to join, but I have people over."
"Yes, I gave them napkins. I'm 24 years old, Mom."
"Hah, no, I don't have any, but I can cast a protection spell instead... Sorry, it's a DND thing. Anyway, gotta get back to the table!"
"Okay, so I was wrong, no Initiative roll yet, but if you succeed on your Strength check, it will trigger a surprise round first, then roll for Initiative."
"Sure, we can roleplay it."