Yeah, I'm doing one of these. Except instead of one character, it will be several from potentially any canon.
100 Things Ash Should Not Do
1) I won't poke Pikachu in the stomach when he's sleeping. Ever.
2) I shouldn't laugh about Professor Oak being molested by Muk. Yes, Brock told me what 'molested' meant.
3) I should stop lying to Characters of the Day. I'm never going to come back to see them again.
4) Same with the Pokémon I left behind.
5) I shouldn't tell Dawn her hair has a few loose strands.
6) I shouldn't tell May that she forgot to put on her biker shorts.
7) I shouldn't tell Zoey that I thought she was a boy when I first met her.
8) Same with Anabel.
9) And Angie.
10) I shouldn't call Dawn 'Dee Dee' or 'Pikari' again.
11) I should stop sending out Pokémon in battle against its type disadvantage.
12) Even though I think I can find a way to win, it doesn't always work…
13) I shouldn't tell Gary that I was going to choose Squirtle as my first Pokémon.
14) He made fun of me…
15) I shouldn't encourage Barry to drink coffee. Ever.
16) I shouldn't tell Paul to wear a dress because he's PMSing.
17) Dawn told me to say it, but I didn't know what it meant until Brock explained it to me.
18) That was gross.
19) I shouldn't ask to see Brock's eyes.
20) I shouldn't stick a Bug-type Pokémon in Misty's face.
21) Unless I want a face full of mallet.
22) I shouldn't give Pikachu apples whole. Only slices.
23) I shouldn't have given Butterfree away.
24) Or Pidgeot. Or Larvitar. Primeape. Squirtle. Charizard. Gliscor. Lapras. Haunter.
25) I shouldn't get rid of any of my Pokémon. Ever.
26) I'll never be a Pokémon Master at this rate…
27) I shouldn't ask Mom who my father is.
28) I shouldn't wonder if Professor Oak is my father.
29) I shouldn't wonder if Giovanni is my father.
30) I won't bring up the Porygon incident.
31) We will never speak of that again.
32) I shouldn't tell anyone that I'm available. I don't know what that means.
33) Huh, Serena? …It means what now?
34) I shouldn't tell Mom I've had a gun pointed at me before.
35) Or several.
36) I shouldn't ask Iris how to swing from branches. Ever.
37) I shouldn't ask where the meat from the hamburger I'm eating comes from.
38) Brock told me not to ask. I'm not sure why.
39) Cilan, too.
40) I shouldn't wonder why I'm still ten years old. My birthday was a few months ago.
41) And a few years ago.
42) I shouldn't ask Tracey what he does at Professor Oak's lab.
43) I shouldn't ask Professor Ivy personally why Brock doesn't like the mention of her name.
44) I now know why…
45) I shouldn't tell Mom that I've seen a man with inflatable breasts.
46) I shouldn't ask why my voice suddenly changed during my journey through the Battle Frontier.
47) I haven't even hit puberty yet…
48) I swear I'm older than ten.
49) I shouldn't wonder why Pikachu is not at level one hundred yet.
50) …Wait, what are levels again?
51) I shouldn't tell people that most of my Kanto badges were just given to me instead of actually battling for them.
52) …I mean, "I worked hard for those!"
53) I shouldn't make Sabrina mad. Ever.
54) I mean it. Don't you do it either.
55) I shouldn't ask Brock about how his mom magically came back to life.
56) I shouldn't give Pikachu another bottle of ketchup.
57) I shouldn't tell Mom that I've died before.
58) Man, if I tell Mom anything else, she'll never let me venture out again…
59) I'm surprised having died hasn't done it yet.
60) I shouldn't wonder if that kid I saw in the past was Professor Oak.
61) That'd be really weird.
62) I shouldn't ask if Harley's ever had a girlfriend before.
63) May, you almost got me killed asking that.
64) I shouldn't ask Bonnie to smack Clemont every time he thinks so negatively about things.
65) Last time she resorted to hitting him in the face with a book and now she's not allowed to do that anymore.
66) I shouldn't give Gary's fangirls his phone number to get back at him for all those years of teasing me.
67) I said I was sorry! Those girls were nuts.
68) I shouldn't try to break Trip's camera to get back at him.
69) Brock, I'm not going to say that because this is number sixty-nine! That is disgusting! What does the fact that this is number sixty-nine even mean?
70) What, Tracey? It's how Pokémon eggs are made? I thought we didn't know how Pokémon eggs were made? How are they made, then?
71) …I shouldn't ask how Pokémon eggs are made…
72) I shouldn't tease Serena about whether she has a crush on me.
73) What, Clemont? Serena doesn't have a crush on me, that's silly.
74) ...I shouldn't ask Serena about whether she has a crush on me...
75) I shouldn't ask what those triangular snacks Brock makes are called. He keeps giving me different answers.
76) …Huh, Cilan? What's a rice ball?
77) I shouldn't joke with Misty about destroying her bike again.
78) I shouldn't introduce my Glalie to Iris.
79) I shouldn't ask Max why he looks like Conway.
80) Max was very offended…
81) I shouldn't give Barry Paul's number to get back at Paul.
82) I shouldn't put Barry and Bianca in the same room together.
83) It looks like a Tornadus just ravaged the place…
84) I shouldn't tell Cilan I've crossdressed as a maid before.
85) He won't stop bugging Dawn and Brock for the pictures…
86) I shouldn't tell anyone I've crossdressed several times already…
87) I shouldn't jokingly tell Officer Jenny that Brock is someone that 'ladies should be aware of.'
88) I shouldn't tell Mom that I may have actually killed someone.
89) Hey, she was trying to kill me first. She may have survived, we don't know.
90) No, Mom. The Pokémon World isn't that dangerous.
91) I shouldn't ask Vincent about if his name used to be Jackson.
92) He got really mad about that.
93) I shouldn't look up what fanfiction is on the internet.
94) Misty seriously warned me about that.
95) So did Brock, Tracey, May, Max, Gary, Dawn, Iris, Cilan, Serena and Clemont.
96) I shouldn't ask what a Missingno. is.
97) …Why? What's so bad about it?
98) …We will never speak of that again.
99) ...I really should not have looked up what fanfiction is...
100) …I seriously need to find a way to shorten this list…
So get those requests underway, if you wish. No guarantee that I will do every single request. Not every list will be a list of one hundred. They all will vary.