Once my roommate’s boss saw me and my roommate couldn’t afford something we wanted when we ran into each other at the store by coincidence. A few days later I visited my roommate at work but forgot to bring something up from the car. His boss offered to go down and get it out of the car for me because I was having some trouble walking after hurting my ankle earlier that week. I gave him the keys and he left to go get what I had left behind.
My roommate and I got caught up chatting and eventually realized that his boss had been outside looking for about 45 minutes. He soon came back up and told us that he had only been gone a few minutes and that we had just not realized what time it was when he left. It was weird but we just let it slide. After I left the office to go back home I got to my car to find that his boss had taken my car to the store and bought us the item he had seen us put back after not being able to afford it and some groceries for the upcoming week. This is one of the best surprises I have ever received and it meant a lot to my roommate and I that his boss cared enough to do that for us.