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Any headcanons for Yellow/Leaf, Lisia/May, and Winona/Kris?

Yellow/Leaf

They’ve known each other since childhood, as Yellow is an old friend of Red and Green’s, and Red is Leaf’s older brother. However, they were never super close as children due to their age difference and having their own friend groups.

They reconnect later on after Leaf joins Team Rocket and begins investigating Mewtwo around the same era as the Gen 2 games. Yellow was also investigating Mewtwo on her own, so the two met by chance and decided to work together. I’m still fleshing out how their investigation goes, but the endgame is that they become close friends and are able to befriend Mewtwo.

They end up pursuing their own paths - Yellow goes to school to study to become a Pokémon Doctor, while Leaf starts working for Green at the Viridian Gym. The whole time they’re supporting each other’s different goals though!

At some point, they start dating and eventually move in together once Yellow graduates and Leaf inherits the Gym from Green (who retired to become a Professor). The two buy a house in Viridian, near the forest, that Yellow also runs a small clinic out of.

Their daughter and only child, Amaryllis, was a surprise and was born before they got married, though they got engaged after discovering Yellow was pregnant. They were also surprised when she was born with bright red hair, though this made Leaf very happy as it’s her mother’s hair color.

In the fankid era, Leaf continues to be the Viridian Gym Leader, while Yellow runs the clinic, focusing on taking care of the various wild pokémon who might get injured. Amaryllis is a fairy-type trainer with aspirations of becoming a Gym Leader herself.

Lisia/May

My OTP so I have a lot for this ship.

They’re a couple who gets together quite quickly! They start dating sometime in the post game of ORAS, probably after the Delta Episode, which is when May decided to try out being a coordinator after spending so long being a trainer.

Their relationship is pretty similar to what plays out in the game, with Lisia taking on a mentor, and eventual rival role to May and encouraging her before and after each contest win, the two growing closer the entire time. I think romantic feelings develop for Lisia first, but she’s hesitant to confess since she’s afraid May doesn’t feel the same, but May for sure caught feelings pretty soon as well, not saying anything since she thought Lisia was totally out of her league.

Eventually, right before the two are ready to compete in the Hoenn Grand Festival that year (I used the anime set up for contests in this verse!), the two both decide it’s the time to confess before they face off against each other in the competition. As they both had the same idea, they ended up confessing at the same time! It all worked out though, since knowing that no matter what, they had each other now and a whole future as girlfriends to look forward to, it didn’t matter who won or lost in the Grand Festival. (As it turns out, neither won, the spot going to Robert as it did in the anime.)

Drew was also there, yes, and he and May had a rivalry like they did in the anime! In this case, it just never became romantic, though of course the two remain very close friends throughout the fankid era. He may or may not have given May some advice and the final push to work up the courage to confess to Lisia. (May returns the favor by bothering him about Harley later on.)

May continued to pursue coordinating for a while, though her endgame career is as a Frontier Brain, replacing Spenser. Her facility is called the Battle Stage and functions like an enhanced version of the battle portion of contests (which is where she got the name from), where challengers have to show off both their battling skills and how in sync they are with their pokémon’s moves and performance. Her title as a Frontier Brain is “Stage Princess May”.

Lisia ends up taking over the Sootopolis Gym from her uncle Wallace when he becomes Champion, having been inspired by May’s success as a trainer. She specializes in Dragon-types (her babies) and is a formidable opponent for any gym challenger, often the last gym leader challenged in the league due to Sootopolis’s location.

The couple live in Sootopolis with their three children, Levi, Evan, and Ione. Levi is a coordinator and aspiring contest idol, taking after Lisia, Evan is a trainer who wants to become the Petalburg Gym Leader one day like his uncle and grandfather, and Ione is an aspiring performer who starts her journey in Kalos. There was a bit of drama with Evan since Brendan and Wally had already mentioned they liked Eve as a girl’s name for their soon-to-be born child, and Evan is awfully close to Eve. May swears it was a coincidence but there was a bit of tension for a while (that luckily gets cleared up pretty quickly.)

Kris/Winona

Less to say here since they’re less developed.

It was actually kind of an arranged marriage. Kris’s family and Winona’s family are both old and traditional and have ties going way back. The elders from both families decided it was time to have the clans join in marriage, something they do fairly regularly every so often and began discussions with clan members.

Initially the pairing suggested was Clair and Winona, but Clair wanted nothing to do with marriage so the elders approached her younger sister, Kris with the idea instead. Kris actually saw it as an opportunity for adventure and figured that since it was kind of a political match, she could still find love elsewhere if she and Winona didn’t click. Hoenn seemed like a fun place to live, so she agreed.

As such, they’re a couple who fall in love after marriage rather than before. They have Amethyst fairly soon after marriage since it was sort of expected of them and both were fine with having a kid, but Gale is born a fair bit later as he was the child they had after falling in love. Amethyst is a coordinator and Gale is a trainer and Evan’s rival.

The romance happened fairly slowly, but after living together for a while, both Kris and Winona found themselves thinking about each other a lot. Kris loved watching Winona work at the gym and how attentive she was to her pokémon (and formed a good bond with all of Winona’s flying-types as well!). Winona loved seeing how dedicated Kris was to her work as a researcher, her care in studying and looking after pokémon and the environment. Before either realized it, they were in love and it just felt right.

Winona continues to run the Fortree Gym, but she’s considering one of her children as a successor, if that’s what they want. Kris, already working for Professor Elm in Johto before moving to Hoenn to get married, simply started working for Professor Birch instead, and later works closely with Brendan once he takes up his father’s lab coat. She focuses on studying pokémon ecology in and around the Fortree area and how pokémon fit into the natural ecosystem, though she will also do the occasional study on pokémon in other habitats in Hoenn as well.

Family Updates

Changed up two of the Kanto families a bit.

Red and Green are now a couple (NamelessShipping). Sage is still Green’s son, but now he also has an older brother named Roy who is Amaryllis’s age.

Yellow and Leaf are now a couple (CrushedWorldShipping). Amaryllis is still Yellow’s daughter.

Sage and Rylla are still the same as before in personality, goals, etc. I will get around to updating their and their parents’ profiles... eventually.