Had this happen a few weeks ago.. our shoe store had a voucher program with a school for a period of a couple weeks where their employees could come and get a pair of black, leather, slip resistant shoes.
The school gave them a 50$ voucher and the employees could buy shoes for any price as long as they were black, leather and slip resistant.
On top of that, they get a 20% discount as school employees in our district.
If the shoes cost more than the 50.
This woman came in with her daughter and they shopped around for a long time before they finally came to the register.
Lady: I'd like to buy these 140$ designer sandals (the opposite of black, leather and slip resistant) and use my 50$ voucher as well as my 20% discount
Me: Ma'am, the voucher can only be used on black, leather, slip resistant shoes. I can give you the 20% discount on the sandals though as you are a school district employee.
Lady: Well, I already have a pair of the proper shoes from last year and I don't need a pair, but I wanted to get these sandals for my daughter and I'd like to use the voucher.
Me: Ma'am, I can't do that. It's against store policy and the school will be checking the receipts to make sure that the proper shoes were bought.
Lady: (wheedling and in bargain mode trying to convince me) what if you just put in that I bought the proper shoe but sell me the sandal.. I'll pay the difference!
coworker joins me by this point
Lady is smiling at us and tries being "friendly" in hopes we will bend the rules
Lady's daughter: embarrassed of her mom and red faced says with a forced smile "it's fine, I don't need them mom!"
Lady: I just don't need another pair of work shoes, and those sandals just cost so much!!
Me: Yes ma'am, they do. The best I can offer you is a 20% discount.
Lady: Oh, I just remembered, I have a 20% coupon, can you just combine them and give me the sandals for 40% off?
Me: No ma'am, we don't combine our coupons/district discounts as it says on your coupon. It'll have to be one or the other.
Lady: Just ring them up and do the 40% off and see if it'll go through!
Me: Ma'am, I can't do that.
Lady's daughter: drops head and is laughing nervously, out of embarrassment "mom it's fine"
Lady: Just let her do it and see what happens!
Me: Let me correct myself ma'am, I can actually physically do it, but I won't because what'll happen is that I'll lose my job.
Lady's daughter is thoroughly embarrassed at her moms lack of shame. We finish the transaction as the lady continues in about how expensive the sandals are.
My coworker tells me when they leave that basically the whole exchange was a repeat of what happened to her out on the floor when she was helping the woman out.