I remember i talked about this in some other thread, but i have to say that pokeshipping out of all Misty pairings came of as most organic, dimensional and authentic for me.
There clearly existed chemisty which exceeded boundry of simple friendship between ash and Misty. At least in Misty case it did with her affection toward main protagonist Ash when we follow change of dynamic and insight in Misty feelings, developing from simple crush in young love by end of Johto.
There has been no other person toward who Misty expressed such concern and care like she did for Ash, Shedding tears and being deeply depressed whenever he was in danger thinking he either died or something bad happened to him. This can be noticed when he was extracted from body in Lavender Town, when he almost drowned in second movie, when he left on his own in dangerous storm to stop TR in Lugia arc during Johto with Brock comforting her.
There has not been person for who Misty showed protective, even at times posessive nasture erupting with jealousy and grudge when other females laid eye on Ash(Giselle, Melody, Macy etc). Blushing like crazy whenever she was accused by others like TR, Tracey, nurse Joy and other characters of being in love with Ash trying to deny it and being heavily defensive.
Or strong level of attachment and devotion in being only girl which rejected several offers to stay with Ash continuing traveling with him. Like when Rudy proposed her to stay with him having everything she could possibly imagine, or character going through conflict and struggling at end of Johto in "Gotta Catch Ya Later" clearly not wanting to leave not only because of not being interested in gym and wanting to continue exploring world, new pokemon and advance her water master career.
But also because she wanted to stay with Ash , with Brock being first one to notice that after his inconsiderate remarks which caused Misty to run away angered and deeply hurted. Because of way Ash reacted to fact of having to split up after so much time.
There is also incident in chronicles where Misty once again rejected other boy(Georgio)because of "her heart belonging to someone else". Which as uncleared as it may be, most likely was referred to Ash imo. Since at end of Cerulean Blues Misty only thinks of Ash in original version, as well Psyduck teasing her, who was very well familiar with Misty feelings making her facepalm and irritated. Reinforcing fact that she indeed holds feelings for someone she knows for very long time.
Granted some would say Tracey, but personally based on history and fact how Misty never displayed such wide diapason of emotions from blushing, denial, jealousy, affection and denial toward him. Ill have to go with supposition it was Ash she thought about.
Im not fan of headcannons only going by facts, so without conrete evidence im sorry , i cannot see anything more between Misty and Tracey than strong friendship and yes care. But in platonic way viewing Tracey as her older brother imo.
Another circumstance which goes in favor of pokeshiping for me was incredibly enjoyable, natural and realistic chemistry present between Misty and Ash. They were like fire and water, yang and zing which were so different, yet so similar in other aspects having everyhing what is needed for exciting, varied and balanced relationship.
From Misty stubborn, impulsive nature to Ash brash, cheeky arrogance . With Misty hotheaded attitude and strong willingness igniting reactions from Ash side which often led to clash and comic scenes, questioning his skills or challeging ego when he becomes cocky having head in clouds. But also in criticized him and pushing to train harder or showed same level of passion and spirit in battling, proving who is better like Misty did(they worked like tandem, ying and yang in that aspect).
Extracting from Ash that emotion and genuine unselfish side through moral support, compassion and understanding(when saving his life, curing him from spore etc which no one else really did) making him humble and more down to earth.
In return Ash selfless nature, great deal of care, bravery to jump into danger and help those who are in need of it also left influence on Misty. In developing better understanding for pokemon(best evidenced in accepting Psyduck over time for who he is), discovering her own talents and qualities as person in becoming more confident and selfrelian.
Geting over issue of feeling inferior and insecure to others(like older sisters), became more reasonable and compassionate as person willing to admit her own flaws and accept criticism better.
Ash presence also often incited her brash, sassy and selfrighteous nature through his reckless,immature behavior with Misty developing need and obligation to look after him and protect of not getting hurt,. She did said that Ash is like "her burden" in second movie if im not mistaken.
Perhaps Ash influence on Misty character came to expression best when doing something she wouldnt done before such as jumping infront of pokemon attacks to protect Gyarados,or becoming more determined in taking charge of things in her hands as evidenced in often pairing up with him in battling TR or other trainers. Going out of her way in trying to catch or stop pokemon for him(like Sneasel or Snorlux) etc.
Testament to Ash and Misty friendship and bond developing to close level became noticeable to me during Johto and later in Hoenn. With their dynamic changing from annoyance and intolerance toward each other flaws, constant fighting and clash to playful teasing. Joking on each oher account through sarcastic remarkes. Moments of conflict where both when being angry and rubbed wrong way resorted rather to yelling, being mad arguing and grumpy rather than punching others and having little to no patience.
Both became more supportive and aware of how much they mean to each oher, With Ash showing lot of concern and care whenever Misty was left missing from group(like in Ursaring forest, when lost with Marill, when Hanson threatened her and Togepi wanting to protect her etc). In return Misty started to admire Ash flaws and naive, easy going nature, giving him unbounded support and encouragement to believe in himself during battles not letting Ash to fall in depression after losing(like at end ogf Indigo league or when losing vs Rudy), comforting him when leaving pokemon behind(like Charizard or Squirtle) or losing tough battles(vs Gary, Whitney for example) .
That can be noticeable during her cameos in Hoenn as well. Playfully joking over his skills as trainer or resourcefulness with Ash answering back to provications leading to lighthearted, natural two way interactions pervated with humor, alacricy and funny dialogue. And Ash inconsiderate behavior making her annoyed, but also very hapy and grateful to be able to be in his company again. Winking, working as team when fighting dr. Doom or colonel Hanson and revealing lot of independence and energy flowing between them.
Ash and Misty bond matured greatly since early days showing through interactions, teamwork and way they react to each other provocations and wisecracks how much they became accepting of each other differences, how much they spent togther and grew to care, appreciate themselves as persons.
I would also like to add that no one else caused such conflic fermenting inside Misty character through course of OS like Ash presence did.
Showing how she herself isn't sure what and how she should feel about Ash and whether he even attracts her or not. Not wanting and having trouble herself to admit and realize if their is something. Which would give out impression how she was confused and undecided herself of whole situation.
The writers were definitely toying around with the idea of Misty/Tracey during the AG series, they even have Daisy imagine Misty/Tracey in a romantic play together. I think about halfway into AG the writers realized they weren't going to bring Misty back to the cast, so they were trying to give her a new ending with Tracey in the Gym.
Whatever they tried to do, they never delivered ending though.
Whole future and in what way Misty story will flow was blatantly left undefined and wide open. Its quite obvious how Misty didnt expressed desire to remain at gym for her whole life filling up for lazy sisters, not being known if she plans to stay or leave at some point to make further progress toward her dreams on more substantial basis. Goals of becoming water pokemn master, learn and discover secrets about water pokemon learning everything she can and potentially one day reach E4 level based on wanting to become like her. Recognized and strongest water expert in world showing everyone beauty and uniqueness of this pokemon type.
It didnt seemed to me that Misty and Tracey are one step away from engagement either. With nothing indicating how they will become pair in future. Maybe in meantime something changed, but since it passed 9 years its anyone guess as far as Misty love life goes. Impossible to know since Misty, her story and ambitions are completely forgotten by writers sadly.