out to dinner, is this a dick move?

[DasLeben]

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Then again, I used to be a waiter, and those who have worked in that type of industry will almost 100% think you are a dick here, while those who haven't may be more inclined to agree with your position.

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Yep, I agree here. I'm a server, and I think that this would be a seriously dickhead move. You're risking getting the server fired just so you can get a free dessert. Do NOT take the restaurant up on that offer if you're at all respectful to other people.