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I can't possibly be the only one who had a lot of issues separating IG and OOG back when I started playing, so what strange experiences did you all have?
I'll share mine first, naturally.
My best friend decided to run a game. AD&D. First level characters, first-second time players. He has our characters get harassed by real-life events without any provocation or reason. One character had his RL girlfriend break up with him, my character was subjected to an enormous piano playing a song that I personally can't stand. Another was given an electrical circuit that he had to solve before we could move on, and it just so happens the GM and that player were both studying such things.
The title for the post comes from the confusion of IC and OOC, when he was talking about school or something, when we tried to clarify who he was speaking to, he said simply, "No, he says it to *you, (the player)"
Nowadays I look back and facepalm, how about you?
The trope actually exists in fiction though as well. This is the 4th wall for a RPG, so for comparison any piece of fiction that extensively makes use of it would be a reference. It has all the same benefits, drawbacks and pitfalls.
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Well, in high school, I ran a game for my brother and three friends. At one point, when they were 14th-15th level, they made plans to slay a green dragon that had a cool backstory. Because of the cool backstory, one of the players, named Scott, hated to see the dragon killed, so he secretly (before the session the party was to slay the dragon in, and unknown to the other players) had his character secretly (in game, and unknown to the other characters) meet with the dragon to warn it of the party's plans, and to make a deal whereby everyone would survive.
Basically, he commissioned master craftsmen to make nonmagical duplicates of each party member's most powerful magic item, cast Nysul's Aura on them to make them seem magical, replaced the real items with the fakes while the party was sleeping at an inn, and gave the dragon the real items in return for sparing the party after they realize their favorite items have been replaced with duds.
The next session, the party assaults the dragon, who is prepared for them, and has their real items lying in his hoard. A couple rounds of confusion follow before the players realize they've been duped, and having noticed that Scott's PC seemed to be arguing about something in Draconic with their enemy during the fight, they quickly determine who betrayed them.
While the others fought for their lives against the dragon, they promised swift revenge on Scott's PC, so Scott had his PC beat a hasty retreat in an Apparatus of Kwalish in the dragon's hoard, scuttling into an underground river to escape the dragon and his fellow PCs.
The rest of the party nearly died, but managed to spot their real items in the hoard, retrieve them, and kill the dragon. By then, Scott's PC had escaped, and became the hated and hunted enemy #1 of the party. I never had to come up with another adventure for that campaign again! The players plotted, schemed, and battled with such passion that the players often became angry at each other (this was early high school, and we were still basically kids). It was a fun campaign, though, everyone was definitely invested in it!