Your endgame scenario for each main character

[matthew11]

I'll give it a try as well.

Ash x Serena: no explanation needed.
Brock x Lucy: one-sided canon on Lucy's side.
Misty x Tracey: obviously canon.
May x Gary: since I can't choose Ash anymore, I went with Gary, thus the nevermet ship. Plus, they both have brown hair.
Max x Bonnie: another nevermet ship. Kinda cute though lol
Dawn x Paul: it's somewhere along the lines of "Opposites attract"
Iris x Cilan: best shipping of BW, but my least favorite ship.
Clemont x Korrina: blondes, blondes everywhere.

 

[Navin]

"Oh! I visited my friend at her house! She's a girl! Oh man! I must be in a relationship with her!"

- every dumb person using BW142 as a "reason"

Anyway, I prefer the harem ending, meaning:

Ash X May
Ash X Misty
Ash X Dawn
Ash X Iris
Ash X Serena

 

[cmarston1]

Tracey x Daisy
Misty x Ash
May x Drew
Max x Bonnie
Dawn x Kenny
Brock x Suzy
Iris x Cilan
Cilan x Iris
Serena x Ritchie (Cloneamourshpping ftw) or Gary
Clemont x Korrina
Ash x Misty
Jessie x James

 

[Mikeachu]

Ash-Misty
Brock-Pewter City Joy
Tracy-Daisy
May-Drew or Branden
Max-Bonnie
Dawn-Kenny
Iris-
Cilan-
Clemont-Robot girlfriend
Serena-Calem, who gets an anime version

Eh, guess I'll just stick Iris & Cilan together just to get this over with.

 

[Queen of Kings]

Ash-Misty
Brock-Pewter City Joy
Tracy-Daisy
May-Drew or Branden
Max-Bonnie
Dawn-Kenny
Iris-
Cilan-
Clemont-Robot girlfriend
Serena-Calem, who gets an anime version

Eh, guess I'll just stick Iris & Cilan together just to get this over with.

I don't think there is an anime version of Calem, and the OP asked us to use existing characters only.

Anyway...

Ash x Serena
Misty x Gary
Brock x Nurse Joy
Tracey x Daisy
May x Drew
Max x Bonnie
Dawn x Kenny
Iris x Cilan
Clemont x Korrina

 

[BubChan]

Ash: May or Misty, i really don't like Serena, her crush get on my nerves, May and Misty can control Ashy boy
Misty: Ash or Tracey, both are great
Brock: Hard one, Marley or lizabeth for me, i never watched the Lucy episode, so i can't ship them
Tracey: Misty
May: Ash, May said that Drew is just a rival for her, so i can't see contestshipping, sorry fans, i just can't
Max: I ship Max with Jirachi, but for humans, i can't see Max x Bonnie, so Misty
Dawn: Kenny all the way, i love Ikari too, but they look like a crack ship
Iris: Cilan of course
Cilan: Iris of course
Serena: Clemont or Miette
Clemont: Serena
Bonnie: Really, i don't know, but maybe Serena
Jessie: And James xP
James: And Jessie xP

 

[Mardeon]

Ash x Serena
Serena is by far the girl protagonist who has the most chemistry with Ash. Plus, her childhood crush is cute.

Misty x Tracey
Pretty surprised to see them together in that special episode and even more surprised to see how well they get along.

Brock x Lucy
Seeing Lucy retribute Brock's feelings was priceless.

May x Drew
Drew can be an arrogant brat, but I love when he's being cute towards May.

Max x Bonnie
Quite obvious, since they're one and the same.

Dawn x Gary
Dawn fangirling all through Gary not because of his training skills (like those cheer leaders from the original series), but because of his POEMS = cutest thing ever!
By the way, I love Kenny, but he's better off with Barry and their bromance.

Iris x Trip
They could spend the rest of their lives calling other trainers "kids" together.

Cilan x Burgundy
Burgundy is pretty annoying, but she loses so much that I feel sorry for her. It's obvious she's got feelings for Cilan, so let's put them together.

Clemont x Korrina
Loved to see him comforting her.

Jessie x James
I struggle with them. I mean, they behave mostly like brother and sister to me. But my guts say they could never be happy apart (such a dramatic statement, but true ).

 

[Chairman Meowth]

Ash x Serena
Serena is by far the girl protagonist who has the most chemistry with Ash. Plus, her childhood crush is cute.

Misty x Tracey
Pretty surprised to see them together in that special episode and even more surprised to see how well they get along.

Brock x Lucy
Seeing Lucy retribute Brock's feelings was priceless.

May x Drew
Drew can be an arrogant brat, but I love when he's being cute towards May.

Max x Bonnie
Quite obvious, since they're one and the same.

Dawn x Gary
Dawn fangirling all through Gary not because of his training skills (like those cheer leaders from the original series), but because of his POEMS = cutest thing ever!
By the way, I love Kenny, but he's better off with Barry and their bromance.

Iris x Trip
They could spend the rest of their lives calling other trainers "kids" together.

Cilan x Burgundy
Burgundy is pretty annoying, but she loses so much that I feel sorry for her. It's obvious she's got feelings for Cilan, so let's put them together.

Clemont x Korrina
Loved to see him comforting her.

Jessie x James
I struggle with them. I mean, they behave mostly like brother and sister to me. But my guts say they could never be happy apart (such a dramatic statement, but true ).

Same here. People pair Iris with Cilan all the time, maybe because they're too lazy and just pair the two unpopular character together for convenience.

 

[Vannmelon]

Ash x Misty

May x Drew

Dawn x Gary (I like Kenny too, but Gary is the only male Dawn has shown interest for. + Her fangirling over his poems were pretty cute!)

Cilan x Burgundy : Makes more sense than Wishful in my opinion...

Iris x Trip

 

[ChiffaniChan]

Ash: Misty - If not her May, Dawn, or Clemont any other ship makes no sense to me.
Brock: Random Nurse Joy - but tbh I can't see him with anyone canon
Tracey: Daisy - only because I have to pick someone. Though he had no chemistry with any character in my opinion.
May: Drew
Max: Bonnie - mostly because they are the same age.
Dawn: Paul - Fanon got me into that.
Iris: Cilan - Fanon, again.
Serena: Clemont - Because I don't see anyone happening for Serena, and the only thing I see happening for Clemont is him and Ash.
Jessie: James

 

[k6666]

Ash X Serena : the reason is because serena crush but imo ash x pikachu is the endgame but rules are rules
Misty x Tracy : I like pokeshipping but it old now , i think misty have move on , i choose tracy because he have good chemistry with misty on show and he often visit her and together with her in chronicles
May x Drew : MY OTP , i love advanced to but Contest give more hint then advanced in my view
Dawn x Kenny : childhood friend crush amd i alwasy see her and ash as BFF and more like sibling or twin
Iris X Cilan : Yin and Yang , Black and White , their chemistry so awsome
Clemont x Korinna : he confort her and have more chemistry also interaction with korinna then with serena

until Bonnie and Max Met , i dont see why should i ship them

 

[Crassus]

Ash x Serena: Nuff said. Ash should get out of his Slowpoke mentality ASAP.

Misty x Tracey: I think for a tsundere girl like Misty, she's best fit with a mature guy who can take care of him. Tracey fits the description quite nicely. Plus they spent a lot of time together.

Brock x Lucy: The only girl ever returned Brock's crush. If not for Max they'd be together already.

May x Drew: They look great together, plus this pair has a really solid foundation.

Max x Bonnie: No particular reason, just that they're in the same age group.

Dawn x Gary or Paul or Barry: Well honestly I'm fine with Dawn x anyone outside of Ash (already has Serena), Conway (creeps me out), and Kenny (who I just don't like for some reason).

Iris x Cilan: Not really too much into these two characters, so I'll just pair them up for convenience's sake.

Clemont x Korrina: They're both gym leaders, and the scene under the moon in XY32 seems pretty shippy if you ask me, so why not?

James x Jessie: Not much to say here.

 

[Hanzer]

Ash x Dawn - my OTP forever, even if I'm really interested in Amourshipping now, Pearl is still the best. The bond between them, the interactions, this friendship, it is just fantastic.

Misty x Gary - I was actually shipping this a lot back in the day, don't really know why...

Brock x Lucy - She has feelings for him, omg Brock why u no hit that?!

Iris x Cilan - I don't see them with anyone else seriously... and they are kind of cute together imo.

Serena x Shauna - ........BECAUSE WHY NOT? But seriously, because I already chose Ash I didn't had better options...

Bonnie x Max - yeah here it goes again, 2 kids same age and many similarities, it works for me.

Clemont x May - I like the concept, their younger siblings are together and then those two start to hang out, and they are all like counterparts right? I mean, Max was the smart guy if I remember correctly, and Clemont is the smart guy while May and Bonnie are more into romance and cute things.

 

[raichu27]

Ash x Dawn (They have a lot in common and some similar life stories.)

James x Jessie

Misty x Brock or Tracey

May x Drew

Max x Bonnie

All I can think of, atm.

 

[ej02]

Ash and serena
misty and tracy
brock and that one hohen battle frontier lady whos name I cant remember right now
max and bonnie
may and drew
dawn and paul
I dont like clemont so lets skip him
cilen and fennel
iris and ah skrew it put her with clemont for him being a mainish character

 

[ErinDingo]

Ash x Serena
Misty x Tracey
Max x Bonnie
May x Clemont

 

[taeuknam]

Ash x Serena
May x Drew
Dawn x Kenny
Misty x Tracy
Brock x Nurse Joy
Iris x Cilan
Max x Bonnie
Clemont x Korrina

 

[Everlasting]

Oh dear, that's fun! I'm basically just listing down most of my OTPs! >:]

Ash & Serena [AmourShipping];
Misty & Tracey [OrangeShipping];
Iris & Cilan [WishfulShipping];
Dawn & Gary [CavalierShipping];
May & Drew [ContestShipping];
Brock & Lucy [LuckShipping];
Jessie & James [RocketShipping];
Clemont & Viola [SiropShipping];
Zoey & Candice [SnowpointShipping];
Bonnie & Max [FourthWheelShipping].

All of them are ships I support, except the last one (I actually dislike it a lot). But hey, I had to complete the circle, so! Though I do like Dawn & Zoey, Clemont & Ash, Ursula & Dawn, Shauna & Serena and Cilan & Burgundy as well.
And best of all, I managed to ditch Kenny. <3 he can die in a hole somewhere i don't care

 

[ChiffaniChan]

Ash X Serena : the reason is because serena crush but imo ash x pikachu is the endgame but rules are rules
Misty x Tracy : I like pokeshipping but it old now , i think misty have move on , i choose tracy because he have good chemistry with misty on show and he often visit her and together with her in chronicles
May x Drew : MY OTP , i love advanced to but Contest give more hint then advanced in my view
Dawn x Kenny : childhood friend crush amd i alwasy see her and ash as BFF and more like sibling or twin
Iris X Cilan : Yin and Yang , Black and White , their chemistry so awsome
Clemont x Korinna : he confort her and have more chemistry also interaction with korinna then with serena

until Bonnie and Max Met , i dont see why should i ship them

I agree with that. I think we all know that the only one that will be with Ash until the end is Pikachu.

 

[Janey4319]

Yo

Ash: Gary
Misty: Brock
Brock: Misty
Tracey: Daisy
May: Drew
Max: Max (the other one from 'Maxxed Out')
Dawn: Barry
- I know next to nothing about Unova and Kalos -
Jessie: Harley
James: Butch

This was hard! So many of my favourite ships overlap! I think I can live with this though!!