My very first geocache ever was in the milwaukee area in a nice small park by the lake. It was a tuesday I think and I just finished with the worst job interview in my life (I suck at job interviews). Anyway the park was pretty empty and I was geocaching alone. While sitting at the cache location, which was on some high ground, I could see a guy walking around on the trails below me. I didn't think much of it and said hi to him on my way out. I stopped to take some pictures of new snowdrops (the flowers) and he came up behind me asking if I was a photographer. I replied that I guess since I was taking pictures I would consider myself a photographer. Well after a bit of talking the guy asked me if I would take some nude pictures of him. I realized this was a bad situation and i was alone and no one else was in the park and I needed to get out fast. I kept trying to leave and he kept coming after me and trying to stop me but eventually I made it to my truck and drove off. I saw a cop driving through the park a few minutes later and reported the guy. People just can't let things like that go. Anyway if worse came to worse I always carry a secret weapon with me, lucky I didn't have to use it.
Second worst was when I was trying to place a geocache and I mistakenly thought that if a road had a road name and sign it must be driveable. I got myself stuck in the woods from 6:00pm till 2:00am before my brother managed to find me and pull me out. I had to work at 6:00am so he came just in time. The skeeters were nasty. Oh and it was the 4th of July, i could hear the fireworks but not see them.