Paul Zak's article in Psychology Today describes how he fell victim to the "classic" Pigeon Drop con at the age of 16 and lost $100 in the process. He probably felt bad about it at the time, but having been conned has payed huge dividends as blog material. His post has been tagged 228 times on del.icio.us, by far the most of any article in the Psychology Today blog world.
In the heat of the moment, loss aversion biases us against placing ourselves in risky situations. However, because of their potential utility as stories, it may be rational to expose yourself to situations with chances of bad outcomes that would at least lead to a good story. Here are some thoughts:
1) The younger you are, the more risks you should take. The amount of time that you will be alive to tell the story is probably greater the younger you are, so the utility of going through a crazy experience is higher.
2) Writers or people who have access to a large audience should take more risks and be more careless than those in the general population.
3) We should feel bad in general when people have unlucky negative experiences, but especially bad if there is no interesting story behind the malaise. It is better to be robbed at gunpoint than to misplace your wallet, story-wise, and we should adjust our sympathy levels accordingly.
4) If you are going to take advantage of somebody, the thoughtful way to do it is to pull off a creative stunt so that your victim will have an engaging tale to tell. It's nicer to conduct an elaborate heist Danny Ocean-style than to simply steal a valued possesion during a lull in attention.