This would probably go under worst for me having thought it, yet probably one of the best due to it's effect. Since it's past the statutes of limitation for blackmail, I'll share.
I guess do to the anonymity here, I've been way more open for some reason than I am in general. I'm friendly, but I just don't tell everything I know like some. There was a guy in college like that, got his jollies trying to embarrass you or if I said something under my breath, he'd repeat it as loud as possible, etc.. He had no filter what so ever. If he thought it, he said it. Example: I skipped a lot of classes. A professor tried to set me and couple others straight. We had to go visit the professor so he could show us the error of our ways and take a pop test- his lure to get us there. It was his assumption that we missed his class to study for another. Of course the genius with no filter informs him that we weren't studying for another class, we just kept catching fish so we didn't get home till 3 a.m.
The guy was a notch above a pervert. One day in class a girl said something suggestive to a friend of mine. The guy was behind the girl and heard it, so later that night I convinced my buddy to inform the guy that the girl would be coming over and had made other innuendos. Knowing the pervert, if set up right, I figured we could get him in a compromising situation and we did. I hate admitting that I thought of this, but he was offered the opportunity for him to come over and photograph the event through the window, for posterity of course, of which he accepted. Time and some other logistics were hashed out. He had no idea I knew of anything.
Fast forward, I video taped the guy (dressed in full camo because that's how you blend in a trailer park) pulling 007 like maneuvers, taking blind snap shots (because he was height challenged) through a window of my buddy's trailer house. His base of operation was a small shed between houses of which provided him cover, except for me videoing him from the brush. He made a few dashing assaults on the bedroom window and the counterfeit actors before retreating to his vehicle in haste.
I can't do it justice, it was quite hilarious to watch in and of itself. Better yet was when we invited him over to watch a movie. Took him a little longer than I expected to catch on, but he did. Since he didn't want this type of thing to really get out or back to his girlfriend, we allowed him to take the video with him and do as he wished with it.
Of course, it wasn't long till he started to get out of line thinking he was in the clear. We then informed him that it would be a shame for one of our copies of that movie to make it's way from a secured location to his girlfriend's mail box. Copies??? He hadn't thought of that.
Like a Pavlov dog, the instant reaction he had to the word "video" was quite remarkable. :lol2: