Munday!
What's the worst situation you've ever put one of your characters into, and what did they learn from it?
There are a few really. I've had Wil branded and forced Sir Guy (basically Wil's adopted big brother) to do it, and I've also had Wil slashed in the thigh pretty badly. Both of those times, in Wil's case were to make him vulnerable enough to accept the help of others (Robin in the case of the slash, Guy in the case of the branding). they also served to let Wil express some emotions he had been holding back for a long time. He's one of those characters who needs to be injured to let his feelings out, really. For Sir Guy, it was a painful reminder of what his position means and that he can't expect to be in it forever if he truly does not believe in meting out justice the way it has been proscribed for him to do. It is the event that really gets him to consider spying for the gang and drives him to join them.
The worst is probably Laenas and the things I have done to her in terms of my original writing. Laenas falls in love with a Manufactured, a clone soldier produced for the sole purpose of filling an army with people. They have interchangeable organs since they share DNA and when a Manufactured screws something up badly enough they are "reprocessed" ie, made brain dead and their organs are harvested. In the case of Laenas, her love for Septimus is illegal and so is Sept's love for her. When they get caught at it, Sept is sent off to be reprocessed.
As a junior officer, Laenas is given a public caning and sentenced to be "re-educated" by her captain with a great deal more force than he has felt the need to use with her so far. It's a punishment for both her and Triarius, who has to be present at the assembly where it is done and watch, and basically admit that it is his failure as a teacher, and an officer that got her punished. As a result of his failure as Sept's commanding officer, he personally gets to conduct the "reprocessing" and Laenas, so that she might learn from the experience, is forced to assist him in the process. Adding insult to injury, Triarius has a secret lover of his own among the Manufactured, his Second (basically a lieutenant chosen from the ranks to be an extra support to the captain, and to intercede with the men when need be) Quintus. Quin is pretty old and in need of replacement organs, and because he is valuable, he is set to receive Sept's organs.
The fall out from this whole event drives the second part of the novel and is what leads Triarius to plot an escape for himself and his unit across space to find a place where they might be free.
In terms of role playing, let's see. I've had characters kidnapped and tortured, but I think the worst of the worst has been the things I have done to Enjolras this year. He has wound up in the hospital on several occasions, both from a serious in-game virus that he was actively dying from until the very last moment, trichinosis, which he is still dealing with the effects of, and had to get rabies shots when he stole a chinchilla from a fur farm and was bitten. Said Chinchilla now lives very happily in his apartment, with a maze. He's also recovering dreams of his past life and is basically experiencing a sort of PTSD like symptom of not understanding the current world very well and wishing to go back to 1832 because he at least knows it even if the outcome is terrible. I tend to pick on Enjolras when I don't feel well. I think because I feel closest to him at the moment because he is a character I have written on and off for many years now and he makes me feel better when that happens. I've also had him shot a few times in canonical roleplays, which was a way to help Grantaire and Joly's players freak out their muses. And I could go on for ages in general but this works for now, I think!