Well, I would not consider my experiences in "crazy" activities to be dangerous, but rather, what is the least expected. I have done a number of activities similar to what you have noted, though they are not particularly crazy in my eyes, rather, entertaining. As for the most absurd decision I have ever made, it actually turned largely in my favor, as well as the favor of many others.

A few years ago, I used to play an online MMORPG in which severs were paired against each other in a three-way war for control over territories. This game included siege weapons, including mobile siege, but they were quite expensive, and they required massive amounts of supplies to create. Our server had seized control of the primary fortress one day, and I spent the entire day upgrading it to its maximum, which required a lot of resources on my personal behalf. However, our server was quite small, so few others were on during this portion of the day, so one of the enemy servers ended up seizing the fully-upgraded fortress in which I spent all day upgrading. After that, I was quite upset, seeing that I really disliked the enemy server (of two) which we were paired up against that week. As a result, my friend and I purchased fifty of the highest-quality mobile siege weapons (which cost a fortune), and we used up the entire supply count on the main battleground. It took us hours to build the siege weapons, but once we were done, about everyone who was on the server had joined in on the raid that we planned to use the mobile siege for. What was originally a server which had approximately 20 to 30 people on the main map per night easily queued over 100 people all trying to join in on the raid. As a result of purchasing and building the mobile siege, our server captured the entirety of the primary battleground, which was unprecedented in our server's history.

Technically, I make decisions like this quite often, and they usually work oddly well. Perhaps it is because the decisions are so absurd that they actually end up working, but it is quite enjoyable nevertheless.