I realized not too long ago that I'm always working the angles. Trying to get stuff free or greatly reduced. Bartering. Haggling. Once in awhile, I have quite a streak.
I had a coupon for a free reusable bag from Trader Joe’s, so I found my 5 items that I needed, took them to the register, and the guy said “Oh, this is the first one of these coupons I’ve seen.” So I jokingly asked, “Do I win a prize?” and he and the manager gave me 6 bonus items, including some pricey trail mix and honey roasted peanuts!
And as if that’s not enough, last weekend I reserved a room at the Hard Rock Hotel downtown, using my corporate discount (totally allowed, even for non-business travel, since I’m paying), and I mentioned that it was my Big Milestone Birthday and could they upgrade me. She said, “I can’t, but ask when you check in.” So, when I’m checking in I’m feeling all silly about it and don’t say anything. But the receptionist says, “I see it’s your birthday. Here’s a free drink coupon, and we upgraded your room.” Hell yeah they did. It was a suite on the 32nd floor, with beautiful views of Millennium Park, Michigan Avenue, the river, the lake. It was spectacular. We paid about a third of the standard rate.
It pays to ask. If you don't ask, you don't what you might be missing out on.