Changing mental patterns

Oops, I did a bad thing. Not that I've never made mistakes as a GM before, but last session I made the worst one I've had in a long time.

I'm running BF through Paizo's Rise of the Runelords, because as a pair we have some sort of gaming ADD where we start and stop campaigns every few months. We had just started the game, and I'm putting him through a sort of prologue to let him get acquainted with the little town of Sandpoint with its lovely people and terrible monsters. The twist is, during this period he's playing a "normal person", not an adventurer, and therefore has no class levels. The idea is that he'll 1.) appreciate his class abilities more once he sees how hard it is as a normal people and 2.) he'll need to avoid or work around conflict as he doesn't have the HP to deal with needless fights and 3.) it would give him some time with his character to develop his personality so that when he picked a class it would be for more than mechanical reasons. We agreed that doing the prologue this way was an interesting/fun idea.

The first mistake is that BF assumed this prologue would last only one session, two at most, whereas I had planned for the events of the prologue to last around five sessions. Oops. I wanted to give myself plenty of time to introduce or foreshadow things that would come up in the adventure path, but with BF's assumption he has been trying to rush through things in an effort to get to the "real" game.

The second, worse mistake blossomed from this first mistake. He assumed that the prologue was to be a short, light-hearted thing, and therefore when his character overheard talk of a mysterious Sandpoint Devil kidnapping a child, he sprang into action, encouraging some locals to go with him to defeat the monster and save the child. I tried to have the NPCs discourage him or shy away from something so dangerous, but BF used every mechanical option available to him, blowing through all of his action dice on his charisma checks. I figured, if it meant so much to him, then I would try my best to improvise something.

Now, the Sandpoint Devil is a strange thing. It appears in the bestiary for the RotR adventure path as a pretty nasty monster with some tricky attacks available. The lore is such that the locals have all heard of the Sandpoint Devil, but all evidence of it magically disappears, so no one really believes in the monster. It's a nocturnal beast with a hatred of the light and a love of terrifying its food of choice (small children) before eating them. Going by this I rule that BF can convince some others to go with him as they don't really think they'll find anything, but that it really is hiding out in a nearby cave "playing" with its food. After some preparation BF and his well-meaning misfits head out into the woods, discover the caves, and march in (expecting goblins or something small and manageable) and run right into the Sandpoint Devil.

Long story short, it kicked his ass.

Generally I avoid making fights where the PC(s) are almost certain to lose but in this instance he was so set on this particular path of action and I had had to improvise the entire session so I just went with what seemed simple rather than what was smart. As I generally avoid making fights that can't be won, BF went into this assuming it was a fight he was going to win. The aftermath was not pretty. His PC survived and he rescued the child, but he was clearly sulking afterwards, completely shocked at that turn of events and only then realizing what my many hints to turn away had meant.

I feel bad about how things turned out as well. I'm not in the habit of discouraging actions, even if I don't think they're a good idea, but BF felt sucker punched by the monster, as all the NPCs had been scoffing at the idea of it actually existing. As a DM I get the most fun out of seeing what crazy plans my players come up with, but here he felt as though he'd wasted the entire session. Worse, he just wanted to finish the prologue here and get into the "real" game and was surprised to discover that the important events of the prologue hadn't even happened yet. The entire session made him feel distrustful and weak, and now instead of going for an wandering adventurous sorcerer-type (like I wanted) he is thinking of making his character a wary, walking fortress of HP and armor, clinging to Sandpoint (which I definitely didn't want.)

I'm wondering if certain settings encourage certain trains of thought. No matter what happens in Eberron I'm sure to make it part of a political power struggle. When we're going through Planescape I let BF do almost anything, so long as he can talk the appropriate NPCs into it. And now that we're doing Pathfinder, I worry that the grim and gritty stance of the setting will encourage me to make defeat the default.

I'll think it over. If I can't run Rise of the Runelords without making BF completely paranoid about every monster and NPC he runs into, then I'll just have to find a way to run "Adventures in Varisia (incidentally there's also a Runelord)".