In a fanfiction, their relationship might develop romantically. They could have shared experiences like saving each other's lives. One time, Ash could be in a dangerous battle and Elesa comes to his rescue. This act of heroism makes Ash see Elesa in a new light. They then start spending more time together outside of Pokemon battles, going for walks, sharing stories about their pasts. As they get to know each other better, feelings of love might start to blossom.
It could also develop in a more mentor - mentee way. Elesa, being an experienced Gym Leader, could offer Ash advice on training his Pokemon, especially when it comes to Electric - type Pokemon since she is an expert in that area. Ash, in turn, could teach Elesa about his unique training methods that he has picked up on his travels. This exchange of knowledge could create a strong bond between them that is based on mutual learning and growth.
At first, Ash and Grace might be a bit hesitant around each other. But as they encounter different Pokemon and face various challenges like difficult terrains or strong wild Pokemon, they would start to communicate better. They would learn about each other's dreams and goals regarding Pokemon. This understanding would deepen their relationship, and they could end up being like family, always looking out for one another.
At first, Zoroark might see Ash as just another human who could potentially be a threat. However, if Ash saves Zoroark from a hunter's trap, that would be a turning point. Zoroark would then be curious about Ash. As they spend more time together, Zoroark would start to imitate Ash's behaviors in a playful way, which shows that it's getting closer to him. Eventually, they would develop a deep friendship where Zoroark would be very protective of Ash and Ash would consider Zoroark as one of his most special Pokemon friends.
At first, their relationship might be filled with tension. Ash is always eager to prove himself in the Pokemon world, and Ursula may see him as a competitor. But as they encounter difficult situations, like facing a powerful villain team that threatens their Pokemon, they start to rely on each other. This mutual reliance could turn into respect, and then slowly, love could bloom as they see the good in each other.
At first, they might be a bit cautious around each other. But as they spend more time together, they start to respect each other's skills. Ash would come to admire May's Contest skills and May would be in awe of Ash's battle prowess. They could become like a team, always having each other's backs, whether it's in a battle or a Contest.
After marriage, their relationship would likely become more domestic. Ash, who has been constantly on the move, would have to adjust to a more settled lifestyle. Elesa, on the other hand, would have someone to share her daily life with. They would probably support each other's careers more closely. For example, Ash could help Elesa with her Pokémon training for any fashion - related Pokémon shows she might be involved in, and Elesa could use her influence to promote Ash's Pokémon battling achievements.
Their relationship could start off as adversarial since Cassidy is from Team Rocket. But as they encounter various challenges, like rescuing Pokemon from a natural disaster, they might start to see each other in a different light. Ash could see that Cassidy has some redeeming qualities, and Cassidy could be impressed by Ash's determination.
Their relationship could develop through shared battles. For example, when they fight together against a strong opponent, they start to respect each other's skills more.
Their relationship could start as a friendship based on their shared love for Pokemon. As they go on adventures together, they start to rely on each other more and more, and it gradually turns into a deeper friendship with mutual respect.
Ash and May's relationship might develop as they help each other out with their respective goals. May could help Ash understand the more artistic side of Pokemon, like in contests. In return, Ash could teach May about battle strategies. As they exchange knowledge and experiences, they would become closer friends. They may start to rely on each other more and more, and this mutual reliance would be the foundation of a strong relationship.
Their relationship could develop through shared experiences. Say they both participate in a difficult Pokemon league. They support each other during tough battles, and this mutual support deepens their connection. Korrina might help Ash overcome his fear of a particular type of Pokemon, and Ash could inspire Korrina to be more adventurous in her training methods. Over time, these experiences could lead to a deeper, more romantic relationship.