This is obviously a while ago and happened in college but was walking out of the dorm when a homeless guy on a bike approached me and asked if I wanted to by a stamp. The guy definitely looked down on his luck, though in hindsight he looked like a drug addict, and me being the non-jaded college freshman chose to oblige.

I knew I had some change in my jacket so I start digging into it as he starts searching for the stamp from his bag of random shit and implying that he would appreciate it if I gave him more than the stamp's worth. Totally get it, and I was prepared to give him the loose change I had since w/e.

That's the when the TIFU happened. He pulled out an obviously used stamp just as I pulled out my loose change and it hits me. I have 23 cents in my pocket, much less than the value of a stamp.

Not knowing what to do, I hand the money over to him and say that's all I have on me as he just stares at me for what seems like forever. I end up breaking the awkward silence by offering him his "stamp" back but he just bikes away with my change.

TL;DR - offered a homeless guy all the change in my pocket for a first class stamp. all the change in my pocket was worth less than the stamp