Reddit, what is the sketchiest transaction you ever had?

I used to collect Dragon Magazine and before the internet, it was difficult to find back issues. One day when I was about 13, I was reading a classifieds magazine and I hit the jackpot - a guy was selling 30 early issues I desperately needed. I called him and begged him to not to sell them before I could get there. He seemed cool on the phone. After gathering all the money I had, I convinced my mom to drive an hour to get them - to Lawrence, Massachusetts which is one of the seediest towns in New England. It's top tourist attractions were arson fires and collapsing decks. We pulled up in front of this triple decker with a mangy dog tied to a fence and a small dirty child wandering around with no shoes. I climbed up to the third floor through a dimly lit hall echoing with Spanish pop music. The door opened to a cloud of cigarette smoke. The guy was covered with paint and smelled like stale beer. "Hey man come on in" pointing to a mysteriously damp sofa. He sat down and starting chatting about the Red Sox. "Ummm Hey I'm here to pick up the magazines?" "Oh yeah yeah yeah. Riiiight" And then he kept going on about other stuff this chick from the club he was going to bang, his dick boss at the painting company, like I'm his best friend or something. I didn't know it then, but he just totally wasted. "Ummm I brought the money. For the magazines." "Cool cool - you got like $20 more?" "No. This is all I have" "Oh ... OK ok. Got any smokes?" "Nope" "Oh" Awkward silence. Then, he seemed to remember why I came and disappeared into a back room for 10 minutes. When he came back there it was, the box of Dragon Magazines. Awesome! They smelled like a cigarette factory, but they were about to be mine. He sat down, took a swig from an assortment of bottles, and started to read them. "Hey do you want a beer?" "I'm just a kid!" "Oh." Then he got really excited. "Hey do you want to stick around and talk about Dungeons and Dragons??!!" "Sorry, my mom is waiting downstairs" He seemed genuinely sad and disappointed, before coming up with his next great idea. "You can come back some other time! I've got dice." "Sorry, I live far away... uhh ... I have to go now" and I backed out of the apartment, box in hand.

/r/AskReddit Thread