I'll start, I was 16 yrs old, just learned to drive and was just driving around when I saw it. It was a 16' homebuilt pretty well constructed of plywood and fiberglass on a trailer, except.. it was in pretty bad condition (hole in the hull, etc) but hey, 200 bucks. Fixed the hole, sanded and painted it, fixed the mast, repaired the mainsail (used nylon fishing line to lash on the sail hanks, etc), all myself and for cheap.
So for my first sail I took her down to lake michigan (8 miles away) and launched her with the help of a friend. A girl I was trying to impress (who was coincidently an experienced sailor with her own hobie cat) was on hand to watch. Pretty much everything went wrong during the launch, and by the time me and my friend got about a mile offshore two things became apparent. First of all, a storm was headed in and a low, planing hull really wasn't equipped for the waves that were starting to be generated. The boat was swamping. Second of all I discovered that the centerboard that had come with the boat was the wrong one, it obviously was barely longer than the well, so basically no centerboard. Ok, should have probably checked that before I started.
At that moment one of the buckets I had for bailing floated out of the boat and away, fortunately I had tied one in so we could still bail. My friend then calmly informed me that he couldn't swim.
I ended up having to get out of the boat and swim it around to point it back to the shore, then scramble in before it took off without me. it was like sailing a rudderless submarine, but we finally got back to shore about a mile and a half down from the boat launch.
The girl had left by the time we got the boat back and she never returned my calls.
It's a miracle I'm still sailing.