Back when I was in high school and lived in the boonies, and we had friends who lived north of the city, we decided to meet at a half way point (The mall) to buy concert tickets from him.
We knew exactly how shady it looked. Night time, empty parking lot, teenagers meeting an older (mid 20's guy) and exchanging money for an envelope. We even joked about it with our friend when he got there, with me in the passenger seat asking if he had the goods and him responding with asking if we had the cash.