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One of my worst experiences was also one of my first.
We travel in the wayback machine to my junior high days, when I first got into fantasy lit via the Dragonlance novels. Met a guy who mentioned he and his friends were playing in a Dragonlance D&D game and invited me to join. I happily accept and bring along another friend of mine.
Turns out they are playing the modules based on the Chronicles line of novels, and the are playing the pre-gens (Tanis, Raistlin, etc.).
What made it so utterly boring was that all the other players and the DM were absolutely determined to make the game turn out EXACTLY like the novels did.
DM: You encounter a group of gully dwarves...
Group (to my friend): You are playing Raistlin. You need to cast Charm Person now.
My friend: I didn't memorize that spell. Can't I just put them to sleep with my Sleep spell and we can just ignore them?
DM: Actually, you did remember that you might need to cast Charm Person so you memorized that spell instead.
Group: OK, there you go. Now cast it.
My friend: Um, sure. I cast Charm Person.
DM: You meet a friendly female gully dwarf named Bupu....
and so on. No room to improvise or do anything original really. The DM fudged all the dice rolls or sometime didn't even bother to roll any dice at all if they would result in even the slightest deviation from that occured in the novels.
Luckily I stuck it out with the group and as we all got older we all became much better roleplayers and gamers. I am still friends with some of these same guys to this day, 20+ years later.