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In January, This American Life aired a segment in which reporter Ben Calhoun went to a few stores and tried asking for a “good guy discount” at the register. Here’s how Calhoun explained it: A friend of his named Sonari Glinton was interviewing a negotiations expert from Columbia University Business School who described a technique where you ask at the register, “Can I get a good guy discount on that? You’re a good guy, I’m a good guy — come on, just, you know, a good guy discount.”

Essentially, what you’re doing is simply asking if the salesperson can give you a discount — just for being a person who is supposedly good in this world.

Ben Calhoun: So Sonari remembered this when he was about to buy these shoes. And honestly, he didn’t think it was going to work.

Sonari Glinton: And I go, hey, is there a good guy discount? And he goes, what? You’ve seen me here all day. You know I want these shoes. It’s tough for me, blah, blah, blah. And he looks at me, and he goes, I’ll tell you what, brother. And he swiped the card.

Ben Calhoun: Like his little authorization card.

Sonari Glinton: Yeah. And he goes, I’ll give you 25% off.

So Calhoun went out shopping and tried asking for a discount. After three failures (and feeling embarrassed about asking for a “good guy discount”), he succeeded in getting a 5% discount off a pot at a cookware shop.

Calhoun concluded that if you have a thick skin, this discount-getting approach may work for you, but that if you were truly a good person, you wouldn’t ask for one: “I know that this is going to sound super earnest. And I’m real sorry about that. But I believe it, so I’ve got to say it. I don’t think that you should try it. I’m not going to try it again.”

Not long after this segment aired, I was at a housewarming party and my friend Adam, a reporter at The New York Daily News, began telling everyone about how he recently got a discount on three pairs of shoes, plus some free socks and a wallet thrown in for good measure. Was it the “good guy discount” in action?

We sat down and talked about it. Here’s Adam.

Too Afraid to Ask?

I feel like I come from a family that, while everyone is polite, when it comes down to it, nobody is afraid to ask for anything. And this is something that has manifested prominently at consumer goods stores — especially ones in which we we will be spending a lot of money. When they’re making large purchases, my dad and my mom aren’t afraid to push the salesman into giving us a couple of freebies.

I was at home in Milwaukee over Thanksgiving and my mom and I had a deal where she was going to buy me a new pair of shoes at Clarks for my birthday. They were having a buy one, get the second pair for 50% off sale, and I planned to get the second pair for myself. I really like Clarks and have a brand loyalty situation with them.

So we walked in there — they know me because I’ve been buying the same pair of Wallabees from them for the past six or seven years. So I went in there and I was planning on buying a pair of Wallabees, and the salesman kind of convinced me to change my look — telling me that I had outgrown the Clarks Wallabees. He showed me few other pairs, and I ended up liking another pair similar to the Wallabees: a wing-tipped loafer, as well as a pair of brown suede bucks. They were all priced reasonably enough that it was feasible for us to buy all three pairs, so it turned into us buying all three of them.

When we were checking out, it dawned on my mom that we were dropping somewhere between about $250 and $300, and she said, jokingly, “Why don’t you throw in a couple pair of socks? We’re spending good money here and my son has bought Clarks his whole adult life.”

The guy was really receptive: He said, “You know what, we are a family-owned company, we have lifetime warrantees, it really is our prerogative in the mold of L.L. Bean and a few other companies to make the customer happy, so why don’t you go for it?”

So I picked out three pairs of socks. Meanwhile I thought about how I needed a wallet, and they had a nice selection at the counter, and I said, “Can I have a wallet, too?”

He waffled. I said, “We’re spending a few hundred dollars here, what’s a $25 wallet?” And he said, “All right.” We started chit-chatting after that, warming up some more, and he gave us the “buy one get one for 50 percent off” on the first two pairs, and he ended up giving us his employee discount on the third pair. I’m sure the retail value of what we bought was close to $340, and we walked out of there paying probably just a shade over $250. It was a really positive experience.

He gave us his name. He said, “You know, we don’t work on commission, but if you fill out this survey, I’ll get some kind of bonus if you mention my name.” I went home and did that. It was a really satisfying experience buying Clarks.

When Do You Do It?

Adam, is this a one-time occurrence?

It’s a stab my dad takes anytime he’s spending a good amount of money.

Another time that stand outs prominently to me was when I was going to college, and my sister was starting high school. My parents were buying my sister and I laptops, and meanwhile they needed to buy a new computer for themselves. We went to Best Buy and didn’t pick out anything fancy — just two modest laptops and a modest desktop, and it was a lot of money for a middle- or upper-middle class family — it was a lot of money that we were spending. It was $3,000 and my dad is on the frugal side.

And my dad said in no uncertain terms to the salesman that if he was going to be spending $3,000, he wanted some perks. And they said, “Well, what do you want?” And he said, “Well, as a matter-of-fact, I’d like a free Microsoft Office suite, and two laptop bags for both of my children.

And the guy said, “I can’t do that.” And my dad said, “If you can’t do that, we won’t make this purchase.” He was bluffing.

But the bluff wasn’t called — I think Best Buy was still working on commission at that time, this was 2001, or 2002 — and the guy threw in those things. It was probably a value of $300. And ever since that happened, it stood out to me as an example of if you’re a customer, don’t be afraid to assertively but amicably ask for some perks if you’re spending a lot of money in one place.

Getting Past Feeling Weird

Does it feel weird asking for discounts or perks? Does it make you nervous?

I definitely feel weird about it. I felt embarrassed when my father did it. I was in high school. And I do feel awkward doing it. I never felt entitled to that kind of empowerment as a consumer, but after I saw my dad do it, it got my gears turning. Why shouldn’t I ask for it? The worst that can happen is that they say no. And if you do it casually, you don’t end up embarrassing yourself or causing a scene.

This is a theory: I do feel like it might have something to do with us being in the Midwest. Relationships on the East Coast — things are matter-of-fact and to the point, and people don’t schmooze as much. But in the Midwest, people are always schmoozing. It’s like a relationship, which makes it easier to say, “Can we work something out here?” That’s my theory. To that end, I would feel more comfortable doing it in the Midwest than I would here.

On the other hand, we’re asked to buy stuff all the time. I’ve been in the Banana Republic where people know me, and people try to convince me to buy more things. And I have a person who cuts my hair and schmoozes with me and tries to sell me products for my curly hair. I don’t feel offended that she’s trying to make that extra money. At the same time, if I need special services from her, I’m not going to be afraid to ask.

Sometimes, It’s Voluntary

This kind of thing has never happened to me before. The only thing that comes to mind is that I used to work at an office next to a fruit stand, and I’d go to that fruit stand every day to buy something. After a week or so, the fruit stand man started putting extra fruit in my bag: “Here’s free fruit! I’m doing this for you because you are my pal!”

Now that we’re talking about it, I have some other examples.

I have a particularly spectacular dentist — like a luxury dentist. He designs his practice for people who are particularly afraid of going to the dentist, and he models the whole experience on certain principles of Zen Buddhism. The place is really relaxing: There is a masseuse, they do foot massage. It was recommended to me from a colleague at an old job, and I thought it was so spectacular, I told my friends about it, one who was then writing for The New York Times. He ended up writing about it which brought him a lot of publicity, and a lot of customers, on top of the 10 to 15 people I had referred to him. As a result, he never charges me for dental work. When he does, he bills it in a way that never comes out of pocket. And it’s not like I needed emergency dental work. And it’s been without me asking for it.

That’s so crazy.

It’s pretty wild!

Where Else Can You Get Discounts?

Have you done this with, say, your cable bill? Negotiated a lower rate?

I’ve done it with annual fees for credit cards. I’ve pointed out that I have good credit and have never missed payment, and they waive the fee.

Last thoughts?

I don’t want to be seen as a penny-pincher, or cheap. But given my place in the world, and what I’m making, I don’t think it’s inappropriate to ask for perk here or there. Quite frankly, I rarely do it. But it’s something I take pride in and encourage people to do now and then.

This post originally appeared on The Billfold.

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