I bought my first bike for 600 dollars on craigslist at age 19 in bumfuck connecticut. A phenomenally shitty 1979 Honda CB750F. I picked it up by myself in a U-haul van with a ramp and ratchet straps and everything. Being the prodigy I was, I obviously decided to take the van to the nearest parking lot, unload the bike, and zip around the neighborhood without a license plate, having never ridden a motorcycle (or bicycle) before. Naturally, I forgot to put the kickstand up before zooming off. (without a helmet) Miraculously, I managed to ride a good distance without any problems until I got to my first left turn. Sparks flew, and I couldn't turn left, much to my confusion. I rocketed straight forwards into someone's yard. (this was at 2AM)

Somehow I was able to muscle the bike left and the soft grass and dirt managed to fold the kickstand up without knocking the bike over and I made it back onto the road after a short tour of the neighbor's lawn. I came back a few nights later with two six packs and a note to apologize for the trail I made.

Ah, the follies of youth.