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Description
It was 1994.  My mother was attempting to play her second video game: Sonic 2.  Her first game, Castle of Illusion, was a Mickey Mouse game in which Mickey can, among other things, pick up apples and throw them at enemies.  So this first question should have been expected:

Mom: "How do you throw the rings?"

And a few minutes later:

"Do I want to get that red thing?"
"Mom--that's Tails."

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1995.  My brother is playing Sonic 2.  He has almost beaten it:  He's up to Metropolis Zone.  My dad is watching, for the first time (really, the ONLY time I can ever remember).

Dad: "That thing just took all your rings away!"
Me: "He's a bad guy, Dad.  That's what he's there for."

-------------------------------------

1999.  My brother is playing Super Mario 64.  He has just read where it says you don't have enough stars "to get past my Endless Stairs!!"  He goes up the stairs anyway.

"What are you doing! It said you needed more stars!" *He continues walking anyway--for 10 SOLID MINUTES* "Now do you believe it when it says you can't get past the stairs?" "Man, now it's gonna take forever to go back down" *turns around--and is only about 3 stairs from the bottom*

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2001.  My bro has just gotten the Postman's Hat in Majora's Mask--the last one he needs to get the Fierce Deity mask.  He comes up with a novel way to celebrate.

*puts on Postman's Hat and follows the postman* "Hey Mr. Mailman! When I grow up, I wanna be just like you!!"

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2002.  My brother is playing Sky Rail Zone in SA2B.  Well, "playing" isn't exactly the word.  That implies he's actually TRYING.  What he's really doing is deliberately jumping off cliffs and rails.

Me: "Stop deliberately falling off cliffs! It's getting old."
Bro: "Just once more...Hey cool, he didn't fall that time!" (This is how I discovered the infamous "Midair Shadow" glitch.)

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2003.  We are introducing a foreign exchange student (John) to the Zelda series through Wind Waker.  He has just made it to the Forest Haven.

Me: "Don't bother fighting the plants John! You don't really need to!"
Bro: "Yeah, John, run away--Like a Real Man!"

-------------------------------------

This next bit requires a bit of explanation--At my church's youth group, the leader would get people's attention with the following interchange:
"God is good..."
Everyone: "All the time."
"All the time..."
Everyone: "God is good."

Back to Wind Waker....

Bro: "Nothing really happens when you fight them--you just get some gold."
Me: "Hey, man, gold is good."
Bro & John: "All the time..."

------------------------------------

1999--My bro had heard that by getting everything in Ocarina of Time (Skultullas, masks, Pieces of Heart, etc.) you could view a secret ending.  So he uses a special cheat to get all 100 Skulltullas, saves the game, then heads off to fight Ganon.  On the way, he sees a Skulltulla.  So he kills it, gets the token, and saves the game.  Now we have 101 Skulltullas, and thus have never seen the secret ending, if it even exists.

Description
It was 1994.  My mother was attempting to play her second video game: Sonic 2.  Her first game, Castle of Illusion, was a Mickey Mouse game in which Mickey can, among other things, pick up apples and throw them at enemies.  So this first question should have been expected:

Mom: "How do you throw the rings?"

And a few minutes later:

"Do I want to get that red thing?"
"Mom--that's Tails."

-------------------------------------

1995.  My brother is playing Sonic 2.  He has almost beaten it:  He's up to Metropolis Zone.  My dad is watching, for the first time (really, the ONLY time I can ever remember).

Dad: "That thing just took all your rings away!"
Me: "He's a bad guy, Dad.  That's what he's there for."

-------------------------------------

1999.  My brother is playing Super Mario 64.  He has just read where it says you don't have enough stars "to get past my Endless Stairs!!"  He goes up the stairs anyway.

"What are you doing! It said you needed more stars!" *He continues walking anyway--for 10 SOLID MINUTES* "Now do you believe it when it says you can't get past the stairs?" "Man, now it's gonna take forever to go back down" *turns around--and is only about 3 stairs from the bottom*

-------------------------------------

2001.  My bro has just gotten the Postman's Hat in Majora's Mask--the last one he needs to get the Fierce Deity mask.  He comes up with a novel way to celebrate.

*puts on Postman's Hat and follows the postman* "Hey Mr. Mailman! When I grow up, I wanna be just like you!!"

-------------------------------------

2002.  My brother is playing Sky Rail Zone in SA2B.  Well, "playing" isn't exactly the word.  That implies he's actually TRYING.  What he's really doing is deliberately jumping off cliffs and rails.

Me: "Stop deliberately falling off cliffs! It's getting old."
Bro: "Just once more...Hey cool, he didn't fall that time!" (This is how I discovered the infamous "Midair Shadow" glitch.)

-------------------------------------

2003.  We are introducing a foreign exchange student (John) to the Zelda series through Wind Waker.  He has just made it to the Forest Haven.

Me: "Don't bother fighting the plants John! You don't really need to!"
Bro: "Yeah, John, run away--Like a Real Man!"

-------------------------------------

This next bit requires a bit of explanation--At my church's youth group, the leader would get people's attention with the following interchange:
"God is good..."
Everyone: "All the time."
"All the time..."
Everyone: "God is good."

Back to Wind Waker....

Bro: "Nothing really happens when you fight them--you just get some gold."
Me: "Hey, man, gold is good."
Bro & John: "All the time..."

------------------------------------

1999--My bro had heard that by getting everything in Ocarina of Time (Skultullas, masks, Pieces of Heart, etc.) you could view a secret ending.  So he uses a special cheat to get all 100 Skulltullas, saves the game, then heads off to fight Ganon.  On the way, he sees a Skulltulla.  So he kills it, gets the token, and saves the game.  Now we have 101 Skulltullas, and thus have never seen the secret ending, if it even exists.