The characters with multiple canons will be presented within the chapter itself. So some responses refer to game!Dawn and others anime!Dawn.
50 Things Dawn Should Not Do
1) I shouldn't be upset every time I lose a contest. It happens.
2) I should stop wondering what the hell was Cyrus's problem was because that is an issue no one can understand.
3) I should stop arguing with my friends when they are right.
4) I should stop arguing with everyone. I seem to think I can win every argument, but I can't…
5) Except with Paul. Cause he's an ass. So I'm always right in arguments against him.
6) I should stop wearing such ridiculously short skirts.
7) Conway keeps looking at me every time the wind blows.
8) I shouldn't keep fixing my hair every time Ash tells me I have loose strands.
9) That's not funny, Ash.
10) I shouldn't question why I am the fandom's main female shipping bicycle.
11) I shouldn't have packed so many outfits on my journey and should have packed more books to help me with contests.
12) I don't even wear most of these clothes…
13) I shouldn't wear the same outfit everyday if I packed so many freaking clothes.
14) I shouldn't wonder how Lucas knows when my birthday is when I'm pretty sure I've never told him.
15) I shouldn't try to kill anyone who calls me Dee Dee or Pikari.
16) I shouldn't keep rubbing it in Ursula's face that she hasn't beat me in a contest once. She'll use those Plusle and Minun against me.
17) That bitch is crazy.
18) I shouldn't wonder why Kenny and Leona look a lot alike…
19) I should stop favoring Buneary over my other Pokémon.
20) They're starting to get really mad about that…
21) I shouldn't look up fanart of myself.
22) Like, the art with myself and Lucas or Barry is really cute, but...
23) ...Is this why I'm the fandom's main female shipping bicycle...?
24) I shouldn't take Ash's lunch when I'm mad at him.
25) It's not very nice.
26) I shouldn't ever team up with Conway in a double battle again.
27) He keeps asking me. Stop it.
28) I shouldn't trip Barry when I see him running toward me.
29) It's not very nice.
30) I should stop being freaked out by the fact that I met my doppelgänger.
31) Wait, who's Platinum?
32) I shouldn't kick Paul in the shin when I'm mad at him, then run away really fast.
33) It's not very nice.
34) Even if he deserved it.
35) I shouldn't jokingly 'Poison Jab' Brock in the stomach when I'm mad at him.
36) It's not very nice. He gets it enough from Croagunk.
37) I should stop being mean to people.
38) I shouldn't wonder how my mom allowed me to walk out of the house in the clothes I'm wearing.
39) I mean, Sinnoh is the coldest region.
40) I shouldn't ever agree to meet someone who sent me a secret admirer message by myself. Especially at night.
41) Dammit, Conway...
42) I shouldn't have stolen Leona's and Kenny's cookies from them when we were in kindergarten for calling me Dee Dee and Pikari.
43) I should stop letting Piplup act like he's superior to everyone else.
44) I shouldn't let anyone piss Mamoswine off.
45) Has anyone not noticed how huge Mamoswine is?
46) I shouldn't be mad at Barry and Kenny for having Empoleon while my Piplup refuses to evolve.
47) I mean, Piplup's cute, but Empoleon looks awesome… Let go of your Everstone, Piplup!
48) …I shouldn't try to take Piplup's Everstone…
49) I shouldn't read the weird fanfiction Conway keeps giving to me supporting HeatTagShipping.
50) I should stay away from Conway.