More enjoyable to you, Misty or May?

Without much hesitation ill say Misty. I enjoyed in her rich, highly versatile personality having plenty of enjoyable quirks and traits specific for her knowing how to lift up atmosphere and embellish anime with more humor and drama. She was feisty, spunky, caring, assertive and full of adventurous spirit often playing role of heroine by saving people lives, helping others about their problems and having great sense of humor bringing great dynamics and humor in cast during all 5 years of her run.

I also enjoyed in growth through she went as character, starting as short tempered girl exploding over everything trying to cover up her insecurities with temper, with time gradually growing in more mature and confident character growing attached to Ash and Brock who were her best friends, managed to stand up for herself and grow out of sisters shadow with whole sad background coming from family of glamorous siblings who treated her as runt with most people on travels downplaying her making character all that more sympathetic and easy to relate to. Improved as water trainer greatly learning more about water pokemon establishing close bond with quite a few whether its Psyduck, Marill, Poliwhirl etc helping her later on when she had to directly confront her childhood fear from Gyarados taming it which was sign of her independence and character strength.

While more was left to be desired and i wish she got more growth i can say Misty development as person was gradual and believable giving us insight in her issues and showing various sides on which writers expanded more showing how aside from hotheaded nature she showed to be deep romantic and passionate battler, liked to glam herself being interested in girly things too, showed to like doing pranks having lot of snark but also caring and sensible side as well. Which led to some great character development later on.

I also liked her niche, big devotion in training and using water type she adores so much with no one showing so much fire and love toward particular type like she did. Her determination to learn everything she can to become water pokemon master one day often sharing her ideas and likes with others of same or different opinion like water trainer Marina or Egan. Additionally her story and dream of water pokemon master added mysterious quality to character making her story extremely flexible. Since she used most widespread type having versatile, rich pool of pokemon creating foundation on which competitions could be created to take her forward, or expand on her liking toward Lorelei who she viewed as idol taking her down E4 route while at same time not being dependent on games and pre established paradigm such quests needs to follow not having much room for tweaking according to your own imagination.

I know its been long since she left cast, but part of me hopes we will see her again too.
She has lot of untapped potential, leaving several things about her story unexplored and untied. Like goal of becoming water pokemon master which was unfinished existing several ways through which this dream could be advanced,potential to learn more about Misty seeing her grow as person,catch new pokemon and so on.
Along with experiencing that great dynamic and spunky, strong willed personality she showed.

Next is May which is my second favorite female character in this show. Granted i wasn't happy when Misty left cast and was rather skeptic about her debut in show not enjoying much in her personality initially. However after some time she grew on me liking how she decided not to follow her father footsteps wanting to get away from life at gym not being sure what kind of career to pursue in her life. That is until she met Janet and her Beautifly falling in love with contests at first sight, and i presume sparky Beautifly influenced her decision in getting one as well. with time starting to become interested in contests. Her development as coordinator had its ups and downs having to work hard experiencing several harsh loses adding realism to her quest and i liked how with time she blossomed in strong coordinator finding her place under sun , collected fairly good collection of pokmon growing to like them. Training under Ash guidance helped her a lot too, although it was double edged sword later on getting in her way of going on higher level as coordinator due to ties with past and her battle style starting to imbibe characteristics of trainer battles lacking elegance and beauty pokemon are needed to perform in contests. Her interactions with Max looking after him as big sister, admiration for Ash skill and competence along with curious nature asking Brock various questions having several memorable moments made her amusing and exuberant character.

And while i liked her i guess reason why i still prefer Misty is because of having more rich, and easy to relate personality imo, because i found her backstory more touching as well considering her goal/career more unique never living to full potential unfortunately.

There were basically 2 1/2 good seasons of Misty, but 3 1/2 good seasons for May.

May only started getting stale in the non-Contest episodes of Battle Frontier, but Misty was too stale for most of Johto until Master Quest.

Depends for who. Because while its true how most focus for Misty in Johto happened in Master Quest she was still enjoyable as character having fun interactions with TR(one of most memorable moments was when she was separated with Meowth and James), Brock having talks about romance and love joking with each other or Ash and her playful teasing while sometime getting into clash. Let along various things she did such as playing role as detective, entering events like Seaking contest, taking care of Brock when he was sick trying to cook , being fun to watch her antics with wild pokemon like Teddiursa etc.

Main issue with Misty in Johto until Master Quest was lack of focus, but regardless she still played fun and memorable role in most episodes. Especially in "Johto Journeys"(3rd season), and to lesser extent 4th season.

Can't say i found May boring for most part in BF outside contest episodes either. Sure every character has his moments of staleness but for most part i found May was still fun and enjoyable character there having fun moments such as travel through time, build up on rivalry between her and Harley prior to contests falling for his tricks, when she got Eevee egg etc.

Even with new characters we can't expect that they play role and be interesting in every episode, but what counts is overall appeal and value they bring in general, moments when they do things and interact with others showing whether character is fun or not.

Kasumi was best when she was a tsundere.

Dunno she still seems to have certain tsundere traits with more mature spin added to it.