Most heartbreaking moment?

[Momo(th)]

Basically, what was the saddest part in your trainer's lifetime? (If you guys want to, you can also say spin-off games, but please don't start spamming PMD scenes, mainly because they were designed to be sad, while in the main games, it's basically a unique story every time.)
My most heartbreaking momment in pokemon was when I had gold in '06, lost to Red, turned it off to rematch him, AND MY DATA GOT DELETED!!! ARRRGGGHHH!!
Seeing that was my first game file ever, I won't lie when I say I shed a few tears:sad:

 

[Monoking]

I like that sig...
What's pmd?

 

[Dar]

pokemon mystery dungeon

 

[Zoroark]

I can't think of a single tear jerker moment at all, in all my years of playing. Well, there was that time when I lost an entire gameboy colour, with my gold gamepak still inserted, but that was more of a 'what the hell did I do with that?' moment.

Does that mean I have no soul?

Mystery Dungeon is the one pokemon game I didn't like.

 

[Flora]

Turn on Gold, look in PC and laugh at the funny names, turn off Gold without saving, turn on Gold a few hours later, presented with choice of "NEW GAME" or "OPTION"

Goddamnit

 

[Blastoise Fortooate]

I am now frustrated with what I am doing in the Silver Version I have. I will restart the game and get a totodile for fun and then not save and then get back to my awesome level eighty typhlosion.

I have to go to the bathroom I had better save.

Why do I still have a totodi-NOOOOOOOO

 

[Phantom]

I had challenged the Elite four on... I think it was FR.... I can't remember... but anyways I had forgotten to take out my HM slave, a geodude, out of my party. It was like level six and just a slave that I didn't really care for. So anyways I get to Champion's last pokemon and my charizard faints; leaving me with my level six geodude because I'd run out of revives. Luckily the champion's last pokemon, I remember it was a Blastoise, is paralyzed and doesn't attack. The thing has a tiny sliver of HP left, so I attack. I am so expecting to lose the next move and then it can't move AGAIN! So excited I was going to win I attack, and it's HP goes to zero aaaand...

batteries die.

Yeah it sucked.

 

[ultraviolet]

beating the E4 in HG? I think? then dropping the DS before I got to save and the gamecard moved slightly and it froze. :|

also in lance's room, there's a spot where if you walk close enough the game will automatically make you walk up to him and start the battle. I usually save right in front of people, but the game made me move and I couldn't save! D:

 

[mewtini]

...

ultraviolet are you my twin

only older

And in Platinum, something very similar to Blastoise.

HAHAHAHA I GOT GIRATIIINA. Okay now I'm bored, so I will restart my game and get a Chimchar but not save! And then I can go back to my beloved level 92 Empoleon.

I have to go eat. I gotta save.

HELLO EMPOL--why is there a Chi--NOOOOOOOOOOOOOOOOO

 

[Squornshellous Beta]

How could you possibly do that in a fourth-gen game? You have to purposefully delete your old save file before making a new one, right?

 

[mewtini]

I only remember saving, so...

THE ONLY POSSIBLE ANSWER IS THAT SOMEONE DELETED
MY OLD FILE.

 

[Luxcario]

YES! I HAVE BEATEN POKEMON BLACK! Now time to catch that Dragonite! *runs into tall grass* I need to get myself a drink. (3 minutes later) Mmm...milkshake! Yes, I spilt the milkshake on my DSi. It froze. I had to start a new game.

 

[Spatz]

Battling Regirock in Ruby, try carefully not to knock it out.
CRITICAL HIT

Forgot to save prior. Gah!

 

[Zoroark]

I suddenly think my earlier joking assumption that I have no soul is probably true. Most of these things have happened to me, but I wasn't upset about them. Ever.

...

I think I need a hug.

 

[Vipera Magnifica]

Someone stole my GBA SP before I got a chance to finish Pokemon Sapphire ;__;

 

[Chief Zackrai]

I have two specific, and one general one that kinda happens a lot.

1. Fighting Raquaza, and it's goin awesome. Until Raquaza flees. ;_; This was before I believed in saving right before something important.

2. I was playing White. Made a ton of progress, evolved like three pokemon. I remember saving, like three times. An hour or so later, I come back to the game and I WAS BACK LIKE THREE HOURS OF PLAYING. worst. moment. ever. I haven't played White since, because I was so sad and mad at it.

Generic: Nuzlockes, when one of your pokemon dies. Not one of the new ones you're trying to catch up to the rest, one of the tough and reliable ones. I always cry a little on the inside when one of my favorite pokemon dies in Nuzlockes. It's not fun.

 

[Hawlucha Fanatic]

Well, I have a few bad ones...

Me, age seven: Yay, Pokemon Crystal! Time to go fight Red - wait. "New game"? No "continue"?! NOOOO, MY TYPHLOSION! FLAAAARE!
Me, a bit later the same day: *sniff* Oh well, I still have Silver... no. NOT THIS ONE TOOOOO!

(Internal battery failure. Two games in one day. WHAT.)

Me, age eight: Hey, cuz, can I have Yellow back please?
Cousin: Sure!
Me: Thanks! ...wait. W-where's my level ninety Pikachu? YOU SAVED OVER IT! NOOOOOOO!

(I've still not completely forgiven her for that one. On the other hand, I now have a legitimate level 100 Mewtwo, so...)

Me, age eleven: Welp, I'm bored, I'll go kick Steven's arse... wait, w-where's Killer? I... AHHHH I SAVED OVER IT! I DIDN'T MEAN TO!

(Sapphire. Level 100 Swampert! Rayquaza in a goddamn Poke Ball!)

 

[Eishiba]

When I had my first ever file on my red version. I had cheated with most of my Pokemon and used the rare candy trick to make tons of level 100 stuff. I had traded everything to blue version from red for some reason. Then me and my friend discovered how to clone with a link cable...Somehow when we cloned, we created a Mew. I have no idea but I had a level 92 Mew. So i got it to level 100 and was going to clone it for my friend. So we do, and then I turn my game on and it says, "Game data was corrupted." I nearly shit myself as all my stuff was gone. How sad...

 

[sv_01]

This stuff doesn't happen to me... Since I have an emulator, I can save in the middle of a battle. But sometimes I get Save and Load confused because different emulators have them on different places. So I:
-saved after killing Lugia
-loaded back where I started after training one or two Pokémon from level 40 to level 50. Several times.
-saved on the opening screen (Luckily, nothing extremely important had happened since I saved in the second slot)
And sometimes I just forgot to save after a long time.
But it didn't make me sad. It was more like I was angry at myself, and if I had just lost a lot of progress, I gave up that game for the day.

But as for sad things that happened in-universe, my Azurill's... background in Sapphire might qualify.

 

[I liek Squirtles]

This isn't much of a tear jerker, but more of a 'FUUU' moment. I was at the hospital (because of an asthma attack) the very same week that White came out. I decided to bring my DS, but I left it in the van. I was about to win against Iris. A while later, I told my mom to get my DS because it was cold and I needed to get my mind of the cold. When my mom arrived, I saw the screen was black. It turned out that my mom had pressed the game card by accident.

Also, I was playing Yellow on an emulator, and I was trying to do the Mew trick from memory. I mixed it up and saved after beating the Slowpoke youngster. And that is why I haven't opened my Visual Boy Advance in months.