In practice, however, he finds he can't cope with it, as he lacks real-world experience. He wants the normal, pushy, arrogant Misty he knew...thus, not letting her keep Togepi. We can see this arc in the constant berating of his sexuality, but her eventual mellowing until she had faded into the background.

Since Ash was quite attached to her, this was traumatizing. After this experience, anyone around him "threatening" to mature quickly ends up leaving only for another, more naive fill-in to enter his life.

Gary Oak is what Ash wants to be. He is wish fulfillment. He succeeded and then settled down to a normal life. Ash needs someone to succeed in his world or he won't be able to validate it and will start questioning why he is where he is. It's a subconscious trap to keep him from becoming too aware of his situation.

His mind must have figured out that awareness of the coma would snap him out of it, so it took something the boy already loved and build a way out for him with it. However, Ash is too complacent to make a final stand and fight his way out of it, and cannot escape.

This is why he keeps encountering legendary Pokémon. They're his mind's way of showing him he can do great things if he tries. It's a way to encourage him to push forwards.

Team Rocket are the qualities of himself that Ash deems "negative" but is coming to terms with. Jessie and James want to appease Giovanni, Ash's father figure. To achieve this, Jessie will trick the submissive James into doing her bidding. Meowth especially wants to appease him because he remembers the good times with Giovanni.

This places Meowth in a category known as Ash's (corrupted) innocence. This is apparent because Meowth is able to speak. In fact, the whole reason Meowth can speak is so Ash can eventually accept the aspects of Team Rocket as parts of himself.

Ash had issues with his father, so he put him atop the evil corporation and demonized him. There may be an actual Team Rocket (in the real world), but it's doubtful that Ash's father is their leader. Ash likely feels the split between his parents was partly his fault, but also partly blames his father.

The split caused his mother to move out of the city down to Pallet Town and is one reason why Ash initially embarks on his journey: to escape the turmoil at home. The whole organization, including Butch and Cassidy, is symbolic of his inability to escape his father's machinations.

James is implied homosexuality (which does not necessarily make Ash homosexual) and gullibility, while Jessie is vanity and manipulation. Since Meowth has the potential for rehabilitation and doesn't want to be evil, this once again fits with the conflicting personalities and demonized-self theory.

Team Rocket cross dresses because Ash is exploring his gender, a different facet than what Brock represents (sexuality), and this was a method that allowed his gay/vain side to experiment freely. When he found that it wasn't something for him, he "free" side stopped playing with it.

Max came with May. He played the ego and she played the id with great aspirations in that "session." They worked for a little while but, with Ash being a teenager, his sexuality had to come back into play. He kept reinventing himself and eventually wrote new aspects, but his mind slowly brought the old ones back as a crutch to make the transition easier.

Dawn is Ash giving himself a chance to love. Since he already established Misty as someone he's not likely to go anywhere with, he created a new super female - one that was more like him and less violent. You may note that while both May and Misty had no tolerance for Brock's behavior, Dawn seems to try to shrug it off.

Tracey, the breeder, was a possible future for Ash that he discarded. This future was one that he sent off to work with the professor (Ash's ultimate ideal of a father figure) when Tracey disrupted the dynamic Ash had with his other possibilities.

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