One challenge could be Ash's constant Pokemon journey. He is always on the move, traveling to different regions. This would make it hard to have a stable relationship as he might not be able to spend much time with his secret girlfriend.
Another challenge could be jealousy. Ash has many friends in the Pokémon world, and Trip might feel a bit left out or jealous if Ash keeps talking about his other friends. Also, if they meet other trainers who are interested in either Ash or Trip, it could create some tension.
It could be Misty. They have a long - standing relationship in the Pokemon series. They've traveled together and shared many adventures, so in a fanfiction, it's not a stretch to imagine her as a secret girlfriend.
They could face a powerful new villain who has a team of super - strong Pokemon.
A big challenge can be the unconscious biases that exist in society. It might affect how they are treated in certain situations, like when looking for a place to live. There could be discrimination from landlords. In addition, they may have different experiences growing up in terms of the opportunities available to them, which could lead to misunderstandings in the relationship. But with open communication and a lot of love, they can overcome these challenges.
Maybe it's a new character created specifically for the fanfiction. A girl from a far - off region who Ash meets during one of his journeys. She could be a powerful trainer or have some special abilities that draw Ash to her, and they start a secret relationship.
One challenge could be living in Ash's shadow. Since Ash is so well - known in the Pokémon world, it might be hard for the character to be recognized for their own achievements. Another challenge could be dealing with Ash's impulsive nature. If the character is more cautious, they might constantly have to balance Ash's eagerness to jump into things. Also, they might face challenges from other trainers who assume they are just like Ash or are trying to use them to get to Ash.
One challenge could be distance. Since Ash is often on his journey traveling from region to region, being away from Alola Lily for long periods might put a strain on their relationship. For example, he might miss important events in her life or she might feel lonely without him.
One challenge could be that Larvitar might be very stubborn at first. It's a strong - willed Pokémon, and it might not want to follow Ash's commands right away. Another challenge could be that Larvitar might be targeted by other trainers or Pokémon hunters because it's a relatively rare Pokémon. Ash would have to protect it.
One challenge could be their different loyalties. Ivypool is loyal to her clan, while Hawkfrost has shown time and again that he is more self - serving. This would create constant conflict as they try to be together. Another challenge is the distrust from Ivypool's clanmates. If they knew she was involved with Hawkfrost, they would be suspicious of her motives.
One challenge could be wild Pokémon that guard the berry patches. They might not want Ash to take their food source. Another is that some berries may be in hard - to - reach places, like on top of cliffs or deep in thickets.