How do you handle requests from listeners when your station only plays requests during limited hours? You can level with a listener, as I once did, and say, "We're not playing requests right now, but (the song you requested) is scheduled to come up two hours from now."
"Two hours?" she replied incredulously. "Oh, come on. Be a good guy. I really have to hear it."
"OK," I relented. "I won't be able to play it immediately, but I'll try to play it soon."
Thus, in the next set, when it made musical sense, I played "You Can't Run" by Vanessa Williams.
The listener called me back and said, "Thanks, babe," after I played the song, and no one admonished me.
Sometimes, being an ever-so-slight outlaw is the right choice.