It was 2010.  I had found out who among my friends would be receptive, and who had a violent reaction to anything D&D related.  I invited them to my house for the first time I had played D&D since being a teenager.

The people (names have been changed to protect the innocent):
Melisande - my wife, social worker, late 30s, had played 3rd edition D&D
Zebulon - my friend, computer guy, early 30s, had played 2nd edition D&D
Isobel - also my friend and Zebulon's wife, late 30s, artist, had never played D&D, only collaborative story games

Material components (besides what would be expected):
Primitive beef jerky
Clean mini-notepads
Factory-sharpened pencils
Read-this-and-choose-your-faction handouts
Big cubes of naturally-occurring metal I had painted dice pips on - The "Iron Dice"
Laptop computer

I had been reading OSR blogs:  Middenmurk, Lamentations of the Flame Princess, Playing D&D with Porn Stars, Hill Cantons, Telecanter's Receding Rules, and Blood of Prokopius, among others.

I wanted to run games according to the ideals many of these blogs had been promoting:

• An open sandbox instead of railroading
• Maximum player choice
• Ad hoc DM rulings as much as possible instead of consulting book rules; avoid skill rolls
• Actions, NPCs, places the players find interesting vs. what the DM only finds interesting
• Lots of randomness, tables to let chance and serendipity shape the game, rather than preconceived DM notions

Some of my own proclivities at the time which I can't blame on the blogs:

• No minis.  Never have been a fan of lead miniatures.
• A Dung Age, low fantasy, low magic aesthetic - no buying tickets for a train which runs on magic, for example,
• I wanted to run players through a miserycrawl in which they would appreciate ordinary items as treasure and have to find creative uses or make money from every thing they found - I was reacting to the bloat of fabulous, valuable magical treasure which can be seen in many parts of the modern game.

I made up a newly-converted, still-somewhat-pagan East Slavic setting.  Foreign invasion and civil war, much of it with religious overtones, inspired mostly by Norman Cohn's The Pursuit of the Millenium    It was a wide-open sandbox, but I inserted hooks I thought the players would want to follow up on. There was a haunted village, inspired by this and these and a neolithic barrow.

I showed the players a minute-long movie I had made on the laptop of mood-setting pictures dissolving into one another with a basso profundo Russian Orthodox choir piece as the soundtrack.

They rolled up characters. They read the faction handouts and chose a faction in lieu of choosing alignment.

Isobel - Level 1 Cleric, Faction: Pagan - an old, white-haired man
Zebulon - Level 1 Fighter, Faction: Axe-Wielders - a neophyte sent from the deep forest redoubt of the purist sect, the Axe-Wielders (my reskinned Skoptsy) to spy on the (reskinned Orthodox) majority population of the larger towns and cities
Melisande - Level 1 Fighter, Faction: The Straight Way (Orthodox), but not prone to care too much about whether his companions were SW, heretics or pagans

Everyone started out in a small village church which was sheltering more and more refugees each day.  People filled the church to the breaking point, hygiene was poor, food was running out, people were getting sick & dying, families were living in makeshift tents among the graves outside the church. I passed out the beef jerky to the players to simulate what meager rations might be shared among the NPCs huddled around the campfires outside the church.  I wanted and expected the players to talk to NPCs about places to scrounge more than a living from old barrows, etc., form an expedition to the sandbox location of their choice, and get out of there, maybe with the blessing of the church's priest.

No such luck! The best-laid plans never survive contact with real life unscathed (and my not-so-well-laid plans definitely did not survive contact with real people and the gaming table).

The misery element was laid on too thick and hit too close to real situations in which the only decent behavior is sympathy with the victims, especially kids.  Isobel's character wanted the PCs to make the dangerous journey through the war-torn countryside to the relatively-unscathed city of Polivka, famous for its soup.  Isobel also wanted to lead the near-starving mothers and children camping inside and outside the church to Polivka with the PCs.  A hardened D&D player, swimming like a fish in the tropes of Sword & Sorcery, would jump at the hooks of "treasure for the taking" which various NPCs of various degrees of sketchiness were dangling in front of the players and would recruit expedition members based on their toughness, experience, useful skills & equipment, etc.

Not the case with Isobel, and could you blame her?  Would you trust sketchy NPCs in your own real life and go adventuring with these strangers?  Would you loot tomb mounds and dead villages?  Would you go down into a hole in the ground, possibly filled with hostile beings which want to kill you and which you probably have to kill?

Zebulon took his character on an informal recon around the palisaded village and outside it, using his stealth and woodcraft.  I rolled on my customized events table and showed him on the laptop a picture of something vague and scary in the forest.  He piloted his character back into the village and tried to tell Isobel's character what he had seen, but she was in the midst of inviting the PCs and NPCs she felt were trustworthy to sneak outside the makeshift camp at the church at midnight, exit the village, and have a meeting in the woods to plan a trip to Polivka.

I had imagined the village priest as a kind, sincere, but recently very harried old fellow, who would give people who decided to leave the overcrowded place his gratitude, his blessing and maybe some equipment or information.  But Isobel wasn't feeling that, maybe tapping into her character's anti-clericalism and adding on her own personal anti-clerical tendencies.  She might have thought the priest and his co-religionists were spying on the refugees and PCs.  The rest of the PCs went along with her conviction. I had the more trustworthy-seeming NPCs the party had allowed to join them to voice their doubts about setting off for a secret meeting at night in the woods.

The something scary that Zebulon's character had seen (and still hadn't been able to tell anyone about) came forth snarling from the woods after the PCs and NPCs had set up a campfire in a small clearing.  The PCs (and combatant NPCs) tried to protect the NPC mothers and children.  The creature fought all of the PCs down to zero hit points in a few rounds of combat and had damaged the combatant NPCs.   Everyone ran for the village stockade, carrying the unconscious zero hp comrades. The creature broke off pursuit.
 
It would have been extremely disappointing if the PCs were killed in their first encounter and we had to re-roll new ones.  I suppose I could have given NPCs for the players to control, but I would have rather done that for them later into the session.

Anyway, the PCs rested and recuperated slowly back at the refugee-filled church, with mild admonishments from the priest.  When they were ready to set out again, this time in daylight, this time with the idea of trekking all the way to Polivka and safety, the priest blessed them and gave them some equipment and kind words but no food.

I suppose I could have had the mothers and children refuse to set out from the frying pan of the village into the fire of the dangerous outside forests and long journey ahead, but they were driven by hunger, and I admired Isobel's player-originated quest to escort these NPCs to safety, and I thought that the PCs now might not move out of the village if the moms & kids weren't going.

Other events (determined by my customized tables) happened along the way.  Zebulon's character and an NPC hunted small game and fed the group.  Isobel's cleric cleaned up and reconsecrated a pagan shrine (which her character would get xp credit for).

Then a random encounter with a merchant caravan occurred.  Isobel, used to story games, said, "My character knows this merchant and is deeply afraid of him.  Don't let him see me!"  I should have asked Isobel if she wanted to have the merchant  be fleshed out as a major antagonist, but for all my expressed ideals about player agency, I just had the merchant not recognize her and chat amicably with the other PCs.

Finally, the party got to the gates of Polivka and we decided to halt the game on that note.

I asked Zebulon and Isobel: "Is this fun?"  They said so, and said they liked the use of the laptop for the intro film-let and the various images which were shown at appropriate points during the game.  But when I invited them to play again, they declined and we ended up doing normal dinner parties and things with them instead.

I really should have done better by them.  Next time I DM, I will try not to adhere to all my contradictory idealisms at once.  I will limit the absolute freedom of the sandbox at the very start, because too much freedom is overwhelming.  I will have an initial set-up for the adventure which WILL encourage PCs to descend into dungeons for compelling reasons (I think a dungeoncrawl, because it limits choice a bit, won't be a bad intro to D&D for new players).  I will skip the miserycrawl idea.  

What have you done before, as a DM, which failed miserably?  What do you do differently now?