It seems any mention of tipping is going to bring the same old debate.

I don't have an "aggressive" tip request story but I've had awkward situations when getting hotel room service (this could also be filed under biggest hotel pet peeve). The room service menu states the inflated food prices, some kind of service charge AND a delivery charge. I assume the delivery charge is the tip for the person who brings me the food but I ask just to make sure (not wanting the person bringing the food to get stiffed). The three times I've asked I've been told that they see none of that money and then they stand there expectantly. Then the sucker I am, I of course give them a few bucks even though I've already paid a service and delivery charge.

I don't ask anymore but still feel the need to tip. My reasoning is that I know when people bring something to your door they expect some cash, even if it's wrong. And if I "stiff" them, there's a good chance that it will quickly circulate among the employees that the people in room 2112 are cheap and the level of service will suffer.