Recently, This American Life talked about this good guy discount, and I loved that it didn’t go in the direction I had expected. They sent out a reporter to three different stores where he asked for the good guy discount. He was actually successful in once instance, but ultimately felt that it was “smarmy” and like saying “the thing I’m going to do as a good guy is ask you to do me a favor and cost yourself money, that’s what a good guy I am.”
This has been the problem I have had since the first time I heard about the “Good Guy Discount.” Only a person who is not a good guy asks for a discount for no reason. It’s super pressurey and puts the sales person on the spot when they are already in a position where they don’t have much power. And it is always bad etiquette to make someone feel uncomfortable unnecessarily.
The best way to get a discount is to a) have a good reason (some kind of damage, paying in cash (but only in the type of situation where it is strongly more desirable to get cash), or just genuinely being a good guy. I have most often been given discounts when I didn’t ask for them, and I guess seemed really excited about what I was buying (also sometimes it helps to walk away and think about it and come back). But also, this has MOSTLY happened to me at antiques/vintage clothes fairs where there is expected to be some degree of haggling and you are dealing directly with the owner and they have high incentive to sell as much as possible.