I guess the biggest fail I've had was about a year ago, A whole bunch of of my friends decide to go ghosting at about 10:00 at night. For me and my bes friend, it was our first time. And man, was it a first time! The first house we hit turned out to have a crazy guy living in it. It was in the middle of a field, so we decided to run behind into the cornfield. Well, I guess the guy figured the same, and sent his dog in there. Well, the dog found me first, and it started a beeline for me. But once it came for me, I bashed on the head with this pole I grabbed out of my friends garage just in case for the exact reason. (and everybody laughed at me) Well the dog was almost knocked out and ran back to the guy. He then paused for a minute or two and went back inside. We waited around to see what would happen, and he comes out in a HUMMER with a police SEARCHLIGHT and kept driving back and forth, scanning the cornfield with the light. We just got on your stomachs and stayed there motionless for about 5-6 minutes, then he took the Hummer back inside. We took that as our chance to get out of there. So we followed the gaps between rows and came back out on the street. We were about to cheer when the garage door opens up, and the hummer starts to pull out. We dive into the ditch and wait, but he wasn't going anywhere but that one little part of the street. I signaled that we had better get out of here and started army-crawling in the ditch and the others followed suit. After a while, he guy started to widen his search, and kept passing by us. Shortly after, I realized that my other ghosting virgin friend wasn't there. The others said f*** him, and kept going. I turned back. After a while of Splinter Cell stealth, I found him hiding under a bush, he was in a bit of trouble. The distance to the ditch was too far to away to get in time befor the guy turns around and comes back the other way. So we devised the crazy idea of going to the tree next to us. And we climbed the tree, and we crawled on a branch farther from the tree untill we were directly over the ditch a good ways up. (I think you have the idea by now) and we went through with it. We jumped, and landed without harm in the ditch. The lucky thing was that we landed in a soft, wet part of it, and it cushioned our fall.
So we begin army-crawling in the ditch again, but we we on the wrong side of the street, so as soon as The Guy turned around, we rolled across and into the opposite ditch. We both agreed that we were getting nowhere, so when every he turned around, we got up and ran, then when he turned around and started getting close, we dove down and army-crawled some more. Now, when we walked there, we walked straight for a long time, then turned left, then walked straight for a long time again. So on the way back to our house, we had to turn right. Anyway, I look to my right, and I can faintly see the dark blots that were my other friends running and cutting through the fields back to their house. I gesture to Matt, and he sees them too. After an exchanged look, we both realized that this was too awesome to ruin by cutting through the field.

So we continue the same pattern, until I took a step into a sink hole about 6 inches deep, and go down. Hard. And an unfairly jagged rock was just the perfect lengh from the sinkhole, and where my knee was going to land. Yeah. So it lands on it, cuts through the pants, cuts through my skin, and just about cut everything else in my knee area. Yeah, it hurt, a lot. So I'm laying there, fighting with all my strengh not to scream, and meanwhile The Guy is still looking for us. Matt takes out a small flashlight, waits until the guy turns around, and examines the wound. I have never seen so much blood in one place in my life. It had already soaked up the front of my pant leg. But me being the stubborn being that I am, I tell him that I can still keep going. We had nothing to bandage it up, so I had to make due without. Keep in mind that we still aren't even halfway back to my friend's house yet. So we continue our crawling, but this time I'm on my back doing this kind of rowboat-backstroke thing to eep my knee from getting full of dirt. Oh, man was in painful. After about a half hour of crawling and Matt running and me trying to at least hobble with him, (he kept me on his shoulder) we finally made it to the corner. And The Guy finally gave up and went back in his house, so the rest of the way, we walk together with Matt supporting me on his shoulder. We finally make it back to my friend's house where my other friends thought we were definatly caught.
So we are sitting in the heated garage, and talking about our experiences with this one. And, if you can believe it, me, with the knee that's almost useless, with a lot of blood still coming out of it, breal the silence and say "Let's go again." Everybody looked at me dumbfounded. I'm like, "what, that was awesome!"
Here Matt and I are the ones who had never done this before, and we were the bravest.
I have to say, that choosing to keep following the ditch of ours was a pretty fail thing.
My knee is fine now, but is has this wicked nasty scar/bruise thing on it, I'll post pictures of the knee tomorrow morning.
But yeah, that was pretty much the most fail thing I've done.