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Old February 28th, 2012 (6:05 PM).
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bobandbill bobandbill is offline
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A fairly sweet ending there - not too unpredictable admittedly but a decent one nonetheless I feel, even if I'm not into shipping myself.

I'll note that you'd want to check out your spacing - you only need one line of spacing between paragraphs rather than two (like how I do so here in this post). Two is a bit much is all and not the norm that is used.

I did kinda wonder at why these trainers were all at the same school - that struck me as odd especially as they all came from different regions as well in the first place unless you're setting this in a rather alternate universe which isn't clear and probably would still raise questions. (After all if they're just in trainer school together before starting why does Drew have many fangirls for, well, being in school?) Maybe establishing why that is the case would help and be something to consider. Crush cans sounds like an interesting school concept though, but I can't say I've heard of it before. And Ash seemed to be fairly in character with him thinking it was santa (lolwut), I'll admit. =p
If only she was allowed to bring her mallet to school…
That...would be entertaining I suppose. XD

"Well it's never going to go anywhere unless you tell him! This is a good way to do it." May insisted.
One common error was how you did punctuation in dialogue. If what follows the speech tells us who said it/how it was said then you can usually treat the two parts as one full sentence (in other words, the part following the dialogue flows on and doesn't sound right as its own sentence. 'May insisted.' in this case doesn't quite make sense by itself). Hence you shouldn't use a full stop there after 'do it' but rather a comma. Ie:

"Well it's never going to go anywhere unless you tell him! This is a good way to do it," May insisted.
Note that you can use exclamation marks, question marks, etc in such cases - just not full stops unless the sentence ends at the end of the dialogue (e.g. '"I like cats." Then he danced.').
May blinked. "Not even Ash can be THAT dense, can he?"
"You'd be surprised." Misty muttered.
Same here - a comma should be after surprised rather than a full stop. There's some other instances of this as well. Also note here the spacing between paragraphs/speech was missing as well.

their blunette friend Dawn
brunette, I believe.
She was head cheerleader so she attended pretty much every school sport, whenever there was a spirit day; she made sure that she participated.
At times you make run-on sentences as well - as a result it sounds odd to read it. I'd suggest making a new sentence after 'school sport' (ie '...every school sport. Whenever there was...')

But she didn't look embarrassed, in fact, she looked happy.
Another example of a run on sentence - the commas don't quite work here. I'd suggest replacing the first comma with a hyphen/semi-colon or making a new sentence there.

"Happy Valentines Day Misty."
A comma should be before or after a name when used to address someone directly - like here when Ash calls her Misty. (So it ought to be '"Happy Valentines Day, Misty."')

Hope that helps. Not a bad story all in all; just consider fixing the spacing issues and the mistakes I pointed out. =)
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