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Most heartbreaking moment?

when i erased my Red trainer save file and gave it up to my sister (it was her game, she only let me barrow it until i defeated the elite four)

it was sad becuase i had to leave my team behind, and i had grown close to them.
 
My Silver and Crystal versions still work fine. Strange.

Anyway, my first save file ever waaaaay back in 2002 was on Silver. I started with a Cyndaquil, a little green and yellow fireball that loved with all my heart. I raised it to a fantastic level 91 without so much as a single rare candy (I gave those to the Legendary Cats/Dogs/Gerbils). now, I had a major problem - I could not for the life of me figure out how to get to Brock, being that the Cerulean path to Pewter was blocked off and I'm pretty sure the Seafoam Island route to go around and through Pallet was also blocked. I was so frustrated that I started a new game to take my mind off things, and I ended up saving by accident.

That, friends, was the saddest day of my Poke-life.
 
While not a game play wise thing, hearing N's whole story in the b/w games and all made my heart feel pretty sad.

:(


As for game play, though, seeing my brother's ZAPDOS on his Blue Version turn into a permanent (somehow) Charizard 'M definitely upset me, even if it wasn't my own Pokemon..~
XD;

Plus I don't think he liked being anything but a zapdos. :(
 
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...Opened my Sapphire for the first time in years... time-based events not working as internal battery has died. It was a bit of a "FFUUUUUUUUUUU-" moment.

As for plot-based things in the games, I believe I've never bawled while playing a Pokémon game... until X and Y came around. AZ meeting his Floette again at the end of the games always manages to make me happy and sad at the same time.
 
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