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First time you went...oh cool! etc...

The first time for me would be way back when I was playing Blue and my Bulba evolved, I didnt know pokemon could evolve, lol
 
I've been recently getting into the bettle tower, and any time I get an extremely close win could count as one of these. One in particular involved our last two pokemon out. Jolteon Vs. Vaporeon, guess which one was mine. I was about ready to turn off the game when my HP hit 0, but that Jolteon decided to gloat and use Captivate, Yawn, etc. After the Yawn, Vaporeon's Surf scored a critical hit, leaving it with only a few HP left. But then, it used Thunderbolt...

...and miraculously, Vaporeon lived. She was able to get in one more surf and kill the Jolteon, letting me win. It was awesome and I gained a new-found respect for Vaporeon.
 
I went "Oh cool" when I got my 29/31/28/x/31/31 Jolly Shaymin. I had been SRing since Monday for it and I got it on Wednesday.
 
It's 5, but that doesn't really matter to me. I'm going to have it learn Earth Power and it still OHKO's -SpD natured Heatran 100% of the time and neutral SpD natured Heatran >50% of the time.
 
When I managed to catch Kyogre on my first try in Sapphire. xD It was hilariously awesome for me.
 
While playing Gold I was searching for a Nidorino and during this in my head I thought "what if a shiny Pokemon appeared while I'm searching?" when I got to the grass the first Pokemon was a Nidorino, but it was also a shiny. It happened right after I had that thought.

In Diamond I beat Palmer in his first battle using only Tyranitar. For some reason Palmer kept on having his Dragonite use Stone Edge which isn't very effective against Tyrantiar (he didn't even have Dragonite use Aqua Tail). Due to this Tyrantiar was able to use Dragon Dance without problems. Tyranitar defeated Dragonite with Outrage and then Milotic with the same move - I was surprised its Hydro Pump didn't faint Tyrantiar, only leaving it with small energy - and lastly he defeated Rhyperior with Earthquake.

In my sister's Diamond game - restarted from mine - I was battling Palmer for the first time (the one above was like the 10th time) and I managed to beat him on the first try.

In Emerald, after several failed attempts at it, I was trying to catch Kyogre for like the 6th or 8th time. The previous times I did it I used up many Ultra Balls and Dive Balls. However during whatever my last time was I managed to catch Kyogre with a Dive Ball having used up about only two or three balls.

A similar thing happened with Heatran in Diamond, several failed attempts, and then I managed to catch Heatran with a Dark Ball wasting only a small amount of balls.
 
Getting a shiny trapinch in the desert. I had no idea what it was back then and i went hey cool its a special uber rare different colored pokemon. I knwo thats exactly what it is but hell back then i just thought it was just that and nothing special.
 
Mine was when I was in the safari zone in emerald and a shiny aipom showed up. Although that was not exactly a happy kind of 'oh wow', I was terrified it would run away before I caught it, as even normal aipoms are hard to catch in the safari zone. Caught it, though. Now its a red ambipom.
 
It's a minor "awesome" moment, but in one of my past Pearl files, I went to the safari zone to catch a bunch of Carvanha for their rarely held deepseatooth. Afterwards, I had a good dozen or piranhas with one special one that I trained into a Sharpedo (I got 4 DST's out of it, BTW)

Later, I went Feebas hunting, and just like the Carvanha, caught a bunch of them so I had the right nature for a Milotic. Another dozen or so fish right there.

The cool part was putting the two armadas together in one box, led by Sharpedo and Milotic. If only the two could have bred, I would have had the most awesome fish army, joined together by forced engagement...
 
Do non-main series "Oh cool" moments count? If they do...

I'm really not sure. Maybe when I finally caught Deoxys in PMD1? Or Lugia? I'm really not sure...
 
I don't know about the first time, but I just now realized that you can water all the berries in a dirt patch at once by pressing the Dpad while you're using the pail... I totally did not know that!
 
Catching Registeel for my friend on Sapphire. I had a ton of trouble with the other 2, then...
Registeel is low on health. Lu Bu (his trainer name, not mine) used ULTRA BALL! *R-S breaks out and does something*
Lu Bu used DIVE BALL! Registeel was caught!
I was amazed.
 
The first I went oh, cool! I do that at least five times each time a new game comes out.lolBut the very first time...when I left Pallet Town, and found wild Pokemon in the tall grass. I know, dumb, but I was awed by the game.lolStill am.:D
 
The first I went oh, cool! I do that at least five times each time a new game comes out.lolBut the very first time...when I left Pallet Town, and found wild Pokemon in the tall grass. I know, dumb, but I was awed by the game.lolStill am.:D

XD I was worse. The first time I played Red was when my friend lent me his copy, saying that he had no idea how the game worked and to see if I could find out. Apparently he'd been stuck in Pallet Town for months, so when I walked up into the grass and the whole game took off, I was like "OMG! THIS IS HOW THE GAME WORKS! THAT'S AWESOME!! :D"

I was a pathetic little kid. ^_^
 
lolI was stuck outside Saffron City for months. I couldn't figure out how to get past the guards! I even tried sneaking around them. I only wanted a badge, and to explore the town! I even came to think I'd made a mistake when the St. Anne sailed off, thinking I'd gotten off the ship too soon, and had ruined the game by not sailing on it.lolObviously, I didn't get in, until I brought some water with me.
 
lolI was stuck outside Saffron City for months. I couldn't figure out how to get past the guards! ... Obviously, I didn't get in, until I brought some water with me.

SAME HERE!!

That was one of my 2 major breaks in playing yellow. The first being that I couldn't figure out how to use cut XD It actually took me a year, and I was pretty damn impressed when I worked it out!! :p

As for shinies, EV training and the rest...just, whut. Je ne comprend pas.
 
Mine was when I played Pokémon Blue--my first Pokémon game--for the first time and discovered that the attacks actually had animations. OMG, Bulbasaur actually jerked forward a little when it used Tackle! Charmander's Growl produces musical notes!

Okay, I'm exaggerating my level of surprise, but before I got the game I never dared get my hopes up that the battles would have animations, even simple ones.
 
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