Ok so I have a small problem. My boss has asked me a few times to grab her some lunch from the cafeteria if she's going to be tied up and she says "Just let me know how much it is and I'll pay you back." The problem is that when I hand her the food she never asks how much it was or offers up the money and I feel uncomfortable handing it to her and basically being like "That'll be $7.50."
I don't think she intentionally avoids paying me back but she's very busy and I think it just doesn't occur to her. Sure, $7.50 isn't a ton of money but I can't afford to feed my VP boss all the time. WWYD?

Re: What if your boss owed you money?
I doubt it's inadvertant. When people owe money they know it. Did she think lunch started falling out of the sky?
You cannot afford to keep subsidizing her lunches so next time she asks say you have no cash on you and wait for her to give you the money.
You have to say something. If she's anything like my boss, she honestly does not even think about it or remember. If it were me, I would say something stupid and obvious but non-confrontational like, "Wow, they've raised the prices in the cafeteria. That grilled chicken salad used to be $6.50 but now it's $7.50." That will remind her that it actually cost money. If she doesn't immediately say, "Oh, that's right, how much do I owe you?" then she is doing it on purpose. If she's doing it on purpose, I agree with PP about saying something like, "Oh I don't have any cash on me today, would you mind buying this week since I bought last week?"
click the pic (blog)
This. Are you in a larger company? If my boss didn't pay me back directly - then I would submit my receipt to be reimbursed by the company and let them deal with the boss. Or, if you are in a smaller company and would submit stuff like that to your boss, keep all receipts together and do it monthly or something and just hand her a stack of receipts and say - I figured I would just do this all together - here are the receipts from lunch from May.
In this case - I would absolutely keep all the receipts and instead of asking her each time - I would give them all to her at the end of the month and say "I wasn't really sure how to handle this - but these are all of the lunch receipts for May. Should I give them to you or is there someone else at the company (HR, perhaps?) to whom I should submit these for reimbursement."
I would prepare a spreasheet for him/her with the date, name of the restaurant and total. I would photocopy of the bills. I would then write a very nice email something like this.
Name,
As per your request please find attached a breakdown the all receipt for the priod of _______ to _____ as you requested. I will leave a copy of the attachement in you inbox for review.
I look forward to your response.
Name
Scan the items you copied and attach them to the email.
Then put a print out of the entire email and photocopies in his/her inbox.
That way it's all business (no personal emoting) and is exactly what they requested.
She is taking advantange of you. I call BS on her not remembering. Lunch doesn't fall out of the sky. It starts to add up, and fast. And if the cafeteria takes debit cards, she can certainly give you hers to swipe for her sandwich.
I would mention the receipt - what a waste. To make you pay for it but then not eat it? Jerk!
I would write a small (handwritten) note at the bottom of the reciept "This is from Friday's lunch
" and then I would tape it to her computer monitory or phone or somewhere where she'll see it Monday morning.