Since I'm not (too) biased on Pokémon ships, why not explore how the characters of Pokémon feel about being paired with other people and/or Pokémon? I know this has been done before, but here's my take on it.
Also, if a character has multiple canons, then think of the version that fits who their being paired with. For example, HoennShipping will involve game!May responding and AdvanceShipping will be anime!May responding. If it's something like TwinleafShipping where there is both a game and anime version, then just go along with it. I'm not going to write a separate chapter for every canon's personality.
And if there is a pairing I missed, there is usually a reason for that. I'm not actually going through every single person's pairing on the list; I have a life outside of fanfiction.
Who to start with? Ash is too cliché, so he'll be later. Since there seems to be some running joke with this character's ship names (and because he's one of my favs), I'll start with…
BarryShipping
What is this now? Fans like to romantically pair me with other characters? And you want to know my opinion on them? I'm in a hurry, but I guess I'm up for anything. But if I don't agree with this, I'm fining you!
AnarchySynthesizerShipping – Barry x Sapphire
I'm not sure if I'm aware of person named Sapphire… Whoa, is that the name of the pairing? What is this?
AttentionDeficitShipping – Barry x Jessie
Attention deficit? That can't be me, can it? Um, Jessie? Yeah, I don't think so. Bad guys are not my cup of tea… Or coffee…
AvalancheShipping – Barry x Candice
Candice is a pretty rad chick. I don't really see myself, like, dating her.
BaconcheeseShipping – Barry x Bonnie
I dunno who Bonnie is, but can we please discuss that ship name?
BitterCoffeeShipping – Barry x Georgia
Hmm, coffee sounds kinda good right about now…
BlackCoffeeShipping – Barry, Paul x Silver
…Coffee… Wait, what about Paul?
BoastShipping – Barry x Ursula
I don't think Ursula and I would get along… She seems scary…
BoulevardShipping – Barry x Silver
Silver? Yeah, I'm not sure about him. He reminds me of Paul…in a cold-shoulder type of way. But not in the 'don't ever come near me' way…
BRKShipping – Barry x Fantina
Fantina's a little older… But someone is pairing me with people I haven't even met, so I'm sure this list holds no bounds…
BrokenFaderCartelShipping – Barry x Feebas
HOLDS NO BOUNDS.
CaffeineShipping – Barry x Steven Stone
I could go for some caffeine… Hmm, Steven Stone? Never met the guy, but I've heard he's pretty cool. Cynthia talks about him a lot.
CalendarShipping – Barry x May
I've heard about May before, but I haven't met her either. It's really difficult to ask me about someone I've never met, isn't it?
CalendulaShipping – Barry x Cheryl
Cheryl is really nice. Would I date her though? I dunno.
CaramelMacchiatoShipping – Barry x Cilan
Mmm…caramel macchiato… Oh, Cilan? Never met him either, but he and his brothers are in charge of a restaurant in the Isshu region, I wanna go!
ChallengeShipping – Barry x Palmer
…My dad? Wait, wait, some people support this pairing? WHAT?!
ChocolateCoffeeShipping – Barry x Iris
Chocolate coffee sounds soooo good… Oh, Iris? From what I've heard, so sounds like someone I could be friends with.
ClassDismissedShipping – Barry x Roxanne
Man, if I went to a Pokémon school, I would never study…
ClingyShipping – Barry x Lucas
Lucas is my best friend, along with Dawn, and we're all really close. I could see why people would support the two of us.
CoffeeDessertShipping – Barry, Swirlix x Vanillite
Um, the Pokémon thing is a bit weird, but you guys are really making me crave coffee.
CoffeeKickShipping – Barry x Barry's Hitmonlee
My own Hitmonlee? Wait, this coffee thing is…
CoffeePrinceShipping – Barry x Calem
I don't even know Calem, but…coffee…
CoffeeRainShipping – Barry x Edmund
Guys, seriously.
ColdcoffeeShipping – Barry x Paul
Paul…really doesn't like me… Also, you guys seriously owe me a coffee now.
CollideShipping – Barry x Ash
Ash? Eh, we're friends, but not more than that. Besides, he already has enough trouble with girls, supposedly.
ConquistadorInstantLeprosyShipping – Barry x Muk
WHAT EVEN IS THIS?!
CrescentShipping – Barry x Saturn
Uh, no thanks.
DesktopcoreShipping – Barry x Missingno.
WHAT THE HELL, GUYS? IS MISSINGNO. EVEN A POKÉMON?
DiamanteCitronShipping – Barry x Clemont
I just don't know him.
DiscourageShipping – Barry x Jupiter
*Sighs* Bad guys are a no, for sure.
DoubleShotEspressoShipping – Barry x Kazuki
Seriously, where is that coffee?
EbbShipping – Barry x Empoleon
*Facepalm* Pokémon are a no, also…
EggnogLatteShipping – Barry x Santa Claus
OH DAMN, SANTA CLAUS IS ON THIS LIST?!
EmulateShipping – Barry x Zoey
Zoey and I are friends, but I'm pretty sure we'd never go out.
EspressoShipping – Barry x Rosa
I wasn't joking about that coffee, get someone on that.
FairHairedShipping – Barry x Cynthia
Cynthia? I'd like to score a date with her, but I'm sure many guys would. She's awesome!
FallToGraceShipping – Barry x Arceus
The…God of…all Pokémon…?
FineShipping – Barry x Officer Jenny
For a second I thought this meant we were fine people, but then it hit me…
FrappuccinoShipping – Barry, Ash x Paul
Yes, I'd like four sugars and about twenty creamers.
FunnyYouShouldAskShipping – Barry x Zapdos
WHAT DOES THIS EVEN MEAN?!
GalacticBombShipping – Barry x Mars
I already said no… Are we really only in the G's?
GiveDaddyTheKnifeShipping – Barry x Kris
…I don't even know if this is about the actual pairings anymore so than the names…
GottaGoFastShipping – Barry x Chespin
Oh, ha, ha.
GreenHillPastShipping – Barry x Erika
Two Sonic jokes in a row?
GymContestShipping – Barry x Nando
Nando is a pretty chill guy. Honestly, our personalities are pretty opposite.
HerbalCoffeeShipping – Barry x Leaf
I've never met Leaf. Is she the Champion of Kanto or something? Hey, I ordered that coffee awhile ago.
HotandColdMacchiatoShipping – Barry, Paul x Reggie
Ugh, how does anyone expect me to get through this list without it…
HotCoffeeShipping – Barry x Reggie
AHH, STOP IT ALREADY. Although, let's be honest, how in the world are Reggie and Paul even related?
HotChocolateShipping – Barry x Shauna
I'M SO DESPERATE FOR A HOT DRINK, GUYS.
HyperShipping – Barry x Bianca
This is a popular pairing? Well, I have met Bianca once. We hit it off pretty well, but as for dating… I dunno, I really don't think she would even be interested.
What, people think we're related?
IcedCoffeeShipping – Barry x Marley
I feel like she would be very annoyed with me… Maybe not as much as Ursula, but I haven't had a chance to get to know Marley. What, the guy getting my coffee is in a traffic jam?
JumpIntoTheDarkShipping – Barry x Darkrai
…
KusobokechinkoShipping – Barry x himself
Uhh…
KusomangaShipping – Barry x Pearl
My PokéSpe counterpart? Whoa, that's just bizarre…
LameBrainShipping – Barry x Conway
Yeah, no…
LaughableButaneBobShipping – Barry x Liza (Hoenn)
I seriously cannot get over these names…
MacchiatoShipping – Barry x Hazel
*Grits teeth*
MercurialShipping – Barry x Looker
The detective? Um, no…
MochaCoconutShipping – Barry x Skyla
WHY ARE WE ONLY IN THE M'S?!
MochaShipping – Barry x Francesca
Doesn't, like, someone else have like a billion names involving coffee or mocha or something. Huh, Cilan? Why don't you go bug him? At least he probably has unlimited instant access to coffee…
MonkeyCoffeeShipping – Barry x Yappy
I'm about to throw one of you out of the window.
Mutant64Shipping – Barry x Ditto
AAAHHHHHHH!
NexpressoShipping – Barry x Hilda
Hilda is good friends with Bianca, I think. Wait, IS THAT A COVER UP FOR NESPRESSO?
OrangeTeaShipping – Barry x Tracey
I'm not a fan of tea…
PlasmaCoffeeShipping – Barry x N
I literally do not even care about this list anymore. OH WAIT, IS THAT MY COFFEE? NEVER MIND, I'M SO READY.
PureRedShipping – Barry x Cyrus
AND YOU GOT ME FORTY CREAMERS?!
ReinShipping – Barry x Brock
Ahh, so much better. Brock? Oh, gosh, no.
RichCoffeeShipping – Barry x Platinum
Money only means something if you buy your coffee at Starbucks. Other than that, you only need, like, sixty billion creamers and you're a-okay.
RoomHavocShipping – Barry, Bianca x Tornadus
THAT'S NOT FUNNY.
RoyalCappuccinoShipping – Barry x Serena
What? Yeah, I've already added in twenty creamers, but I don't want the rest to go to waste…
SakugoShipping – Barry x Kenny
We're friends, but that's it.
SanFranciscoShipping – Barry x James
Uhh…
ScatterThingsOftenShipping – Barry x Mint
I'm not that much of a klutz!
SinnohYaoiShipping – Barry, Diamond, Lucas x Pearl
I've heard of yaoi before, but I don't really know what it is?
…IT'S WHAT NOW?!
StarbucksShipping – Barry x Ghetsis
I saw the Starbucks name coming, but…Ghetsis…? Do you guys hate me that much…?
StolenCoffeeShipping – Barry x Rug
There, I think all forty creamers is good enough. Wow, you can't even tell this coffee used to be black.
StrawberrycoffeeShipping – Barry, Iris x Serena
Is this safe to drink? Sure, why not?
SublightShipping – Barry x Magikarp
Man, after seeing pairings like this, I need this coffee hit.
SugarHoneyIcedTea – Barry x Burgundy
Seriously, how many drink pairing names are we up to? *Sips coffee*
TaeBoShipping – Barry x Maylene
Maylene is a really strong Gym Leader and… *Eyes begin bulging* Whoa.
TheUpsideDownShipping – Barry x Giratina
Oh yeah, the room is totally upside down for sure. Giratina's that one Pokémon, right? Yeah, yeah, yeah, the…the that one.
TiramisuShipping – Barry x Lyra
Lyra's a super rad chick, like TOTES! Wait, have I met her? Do I know her? Isn't Lyra an instrument, WHY ARE YOU PAIRING ME WITH OBJECTS?!
ToCureAWeaklingChildShipping – Barry x Nurse Joy
Look, whoever came up with that name is being fined eighty bazillion poke! …That is too a real number!
TorrefatoShipping – Barry x Chili
Dude, do you think Chili can supply me with like unlimited coffee for, like, forever? This shit is gold, man, GOLD!
TripleBakaShipping – Barry, Ash x Gary
BAKA, BAKA, BAKA, NANI GA KOKO MADE ANATA O UGOKASU NO!
TurboShipping – Barry x Staraptor
SHIFTING INTO TURBO MODE! *Darts around the room with his arms out* THEY SHIP ME WITH A BIRD~!
TwinleafShipping – Barry x Dawn
Dawn and I are super best friends, like, I WOULD BUY COFFEE FOR HER. And me, I would buy coffee for me. Not her. I MEAN, AND HER, AND HER!
Ur2SlowShipping – Barry x Quilladin
Gotta…go…fast…! *Continues zipping around the room* THEY SHIPPED ME WITH MORE BIRDS~!
VanillaCoffeeShipping – Barry, Ash x Serena
Dude, can you like…snort creamer?
ZebraMochaShipping – Barry x Zebstrika
IT'S LIKE ELECTRICITY THROUGH MY BRAIN. I MEAN, VEINS.
Final Thoughts
*Hours after Barry has finally crashed…and by crashed, we mean he literally crashed into a wall and knocked himself out*
So yeah, Pokémon shipping sounds really dangerous and honestly, I am interested in only coff—I mean, training. Yeah.