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(warning: Ash. Ash everywhere...)
Palletshipping (Ash & Gary): So much development from Gary seemed to come from Ash (I guess it like that for most MC's though. They just help change everyone). Also it was pretty funny yet cute how Gary got Ash all riled up. While Ash seemed like the brash, reckless, careless, childish kid he was & we all loved, Gary was calm, plans ahead, is informative, calculating, etc... While when Gary got more on Ash's nerves in the beginning, with his character development they get along much more than before and have always respected each other. While they are different it's not so much that they would argue all the time & they did push each other to do their best. Also the whole pokeball thing.
(Dub? Movies)pokeshipping (ash & Misty): So while I may not be a fan of the anime of pokeshipping... I can kind of like it for the movie version. It's mostly because Misty's personality is a little different in the movies were she doesn't seem as hot-headed nor gets as frustrated with ash, & ash doesn't seem to be as irratated with her like he usually is in the series. While that seems more of a writing issue, i just never liked relationships where all they do is argue & put each other down personally. But besides them not arguing as much, I do enjoy Misty's quote from pokeshippers favorite movie 2000 'ash is never alone, cause he's got...me!' Very sweet

and I also like him teasing ash (with also sounding a little impressed with him) in the Celebii movie 'ash climbs just like a mankey!'
OrangeShipping (Misty & Tracy): Misty seems to go good with more mature and less childish guys & usually seems to want guys that would do stuff for her and wouldn't mind helping out. While after Ash left they were seen to hangout some in some of the special episodes. With someone as nice and sweet as Tracy I don't see what Misty has to complain about in him & with.
IndigoShipping (Ritchie & Misty): While Ritchie is mostly seen as an "Ash clone" due to a similar appearance & pokemon, it seems most forget that he was seen more responsible and less reckless. But there is a little personality similarities as well, so I can see Misty liking him a lot because of that, and due to Ritchies calm & one to think things through personality, I think he would fit real well with her.
UniformShipping (Brock, Officer Jenny & Nurse Joy): Brock was a great and sweet man. While the other characters where all "Huh, Officer Jenny/Nurse Joy didn't we see you in the last town?" Brock knew and can tell the difference between all of them. He can also tell when there's an imposer NJ/OJ when the others can't. While he does flirt with every woman, that is the only thing that he has going on with NJ/OJ. Also, even if it was just a 4kidz thing, Brock had his own song saying that those two where the perfect girl for him.
Advanceshipping (ash & may): I do like contestshipping more, but I've grown quite fond of this ship as well. I usually like ships that involve people having similarities & differences between them. After all, I think balence is the key to everything, like human diet, exercising, sleeping, etc...
Anyways, they are both childlike, love to eat, like to travel, and are a bit neive.
Ash isn't too into shopping or dressing up, never really into contest, always loved Pokemon, immature during hoenn, and was a bit reckless.
May started her journey only to travel and was only interested in shopping in the beginning, got into contest when she learned about them but was never interested in Pokemon battling, disliked Pokemon at first, & shown some signs of maturity.
But besides all that there is more I like about them. Like ash seemed like it was the first time May started to want to open up to Pokemon seeing ash & pikachu's bond, as she decided not to yell at him for her bike like she was going to do in that moment. I also like that May took it upon herself to find another ship even when ash snapped at her in that one episode. From that I can see a very successful relationship.
Contestshipping (Drew & May): It was cool how both of them gained respect for each other throughout the series. Also I do have to question if all those roses that he gave to her were all for May's pokemon. Also, of you think about it, May is the one that trained and worked with her pokemon, so obviously he has to have some respect & admiration for her as well.
Blushshipping (Brock & Lucy): The only girl that returned Brock's feelings from the looks of it (well, maybe there was that girl in DP maybe, but it really didn't last long). Too bad those over-protective sisters or fans or whatever ruined any chance of that working. Still it would've been interesting to see how these two would've worked out.
Abilityshipping (Ash & Anabel): I like Angie with ash too. Anyways, since she is a frontier brain or whatever I'm guessing she's pretty smart and responsible. But at the same time her and Ash get along pretty well. While it's pretty one-sided (like with all the girls that crushed on Ash), she had at least got that while liking him (It's unclear whether Dawn & Iris had feelings for him, not trying to bring those ships down js) and gets along pretty well and they both enjoy each others company (again not trying to bring ships down, it's just that him & Misty arguing a lot turned me away from Poke and him & Serena don't really seem to have much going for them connecting-wise. But really I don't mind Poke & Amour and kinda like Negai & Pearl, just things that make me not care for it as much).
Comashipping (Ash & Paul): It's kinda the same reason as Palletshipping, kinda (thoughtIlikepalletshippingsomuchmore). While Paul seemed kinda interested in Ash (following him), Ash was kinda obsessed with him (even during the first gym as he wanted to watch Paul & really wanted to want him to watch). Also, it seemed even though Ash thought Paul was the biggest jerk on the face of the planet, he still tried to be friendly with him. Also what they have in connecting them is Infernape. While we heard that pokemon are a resentation of their trainer blablabla... it was interesting that Ash took him in even when he was Paul's pokemon first & that they worked so well even when Paul & Ash are so different. I guess I like opposite-attract thing, as long as it can be shown they won't be down each others throats all the time. While that might be the case in the beginning, like said above Ash seemed to have changed Paul & they now both have respect for each other.
Pearlshipping (ash & dawn): I'm not big on ash x main girl ships, & I definitely ship them with other people. But I've come to enjoy pearlshipping. After seeing how well they do get along & work well together makes me enjoy this ship. Of course nothing implies ether of them have feelings for each other beyond friendship. But I could easily see it becoming more, & it being a good solid relationship built on trust, understanding, and helping each other along (love).
Coldcoffeeshipping (Barry & Paul): Really, Barry is like some huge fan for Paul, & even after Ash beats him he only admires Paul. When Barry did confront Paul, we all probably thought the same thing: he was going to call Barry an obnoxious twit, that he's easily going to cream him, and tell him to get lost, or something like that. But nope he was much nicer. wut? But seriously, only someone like Barry can stand Paul.
LeagueShipping (Ash & Richie): Mix of Ability & Pallet here. They are similar & get along pretty well. But also Richie is more mature and think things through more than Ash. So while they are different to help mix out well with each other, they are similar in personality as well so they won't fight as much.
CollideShipping (Ash & Barry): Both of them are very hyper & overconfident (just... Barry is 100x more and more than Ash ever was). Also, while Ash found him annoying, he did look out for him and they seemed to somewhere in the series became pretty good friends.
FrappuccinoShipping (Ash, Paul, & Barry): Well, I like collide, coldcoffee, & coma, so why not all 3 of them together? Really, I would just be copy & pasting reasons here, but I've already mentioned why separately, and don't want to be annoying be repeating myself over&over&over... But hey we got 3 different characters here that have all been impacted one way or another by each other. While Ash & Barry can for the most part get along, they can be kept from getting into too much trouble with Paul around. And like Barry would take Ash seriously. He would defiantly listen to Paul any day of the week instead of Ash. He idolizes him after all. While Ash wouldn't take Paul's bs as much as Barry would & would also try to keep Barry from being too controlled by Paul so it all works out... Kinda.=x
Pearlshi3shipping (Gary, Ash, & Paul): Well like I said, Pallet & Coma is pretty similar, so why not have all 3 together? Well like above I really don't feel like repeating but why I like them so much is mentioned above (opposite but can get along, changed each other, helped them do better). Also with someone like Ash, I bet it would be nice to have someone else who isn't as hyper and someone good where they can just sit & chat.
Appealshipping (Dawn & Zoey): While they seem different, it helps even out their personality. They both get along quite well, and while Dawn's bubbly & charming personality can mellow out her out a bit, Zoey with her help can get Dawn prepared & has also given her some confidence. I'm usally not a big fan of fem-slash, but I really liked how well these two got along.
CloneShipping (Nurse Joy & Officer Jenny): Both unique girls, both everywhere. There's a lot of NJ's & OJ's out there and some had their own unique & individual character. But what's seen most in Nurse Joy's is that they are nice, caring, sweet, & responsible while most Officer Jenny's are quick to judge, very serious about work, & seem a bit little hard to get to know. So I think they can get along pretty well and while different, can blend pretty well. BBB
Negaishipping (ash & Iris):again not big on ash x main girl ships, but I find this an extremely underrated ship that I've grown to like. I am not a big fan of BW, but I've come to appreciate Iris & see good potential with this ship. There may not be a lot of 'hints' placed throughout the series for them, but there is all lot of things negaishipping has from other main girl ships that I've noticed other people like about the other main girl ships (besides may) with ash.
Iris is quite similar to Misty but got on more friendlier terms with him, as they swang on trees while Cilan was busy and ash ditched Cilan (from a subway boss battle) to have more of a 'date' than any other pokegirl & both enjoyed their time.
Iris got along great with like dawn did (as noted above) and was pretty similar to him as well.
With Serena people actually like some things about it that actually happened with Iris. Fact time: Iris was the one who stopped the bike gag and was the first to be asked by ash to travel with him.
Diodeshipping (Ash & Clemont): My gosh how Ash gets all excited with his inventions and how shy Clemont acts around him itsjustsocuteimsorry! They also get along great despite being pretty different, since Ash is brave & outgoing and Clemont is a bit shy and doesn't have much confidence in himself. But with how encouraging and kind Ash is he's really is helping Clemont get the courage he needs, and they both have some great respect for each other. And dang are they comfortable around each other.
SnapShipping (Snap-I mean Todd & Ash): Mostly at the end of Snap the CotD's episode, I just really like how they got along. It was also funny watching them interacting with each other.
Neoshipping (Cassidy & Butch): They work together so well. I'd say it's much better than RS and seem to really enjoy working together and enjoy each others company. They never put each other down, but say good things about each other from what I remember. Also, Cassidy mostly remembers his name while everyone else in the show angers him by messing them up. So I can really see a relationship working out between the two.
LaserbladeShipping (Clemont & Korrina): I think Clemont is just what she needs, as well as Clemont needs a girl like Korrina. Clemont is mostly mature and nurturing and got her to talk to him about her and Lucario's past, and Clemont needs a laid back but headstrong and outing girl to mix well with his personality.
Aureliashipping (ash & Lillie): I just think would they mix well together. Lillie is afraid of touching Pokemon but likes to learn about them, while ash loves Pokemon and isn't afraid to show it. I could see Lillie being a good influence to ash to study, while ash could impress her with his experiences he had with Pokemon & give her knowledge she might no be able to find in a book.
Blueangelshipping (ash & Lana): I just find their meeting adorable really. With ash being a fool out of himself & them both laughing. In the anime she seems more quiet while ash is brash & loud so I can see them helping each other grow.
Alolashipping (ash & mallow): they seem to get along nicely. Both are very friendly in nature. Plus mallow likes to cook and ash likes to eat.