One scenario could be that Wendy's Pokemon was stolen by a villain. This would be a very distressing situation for her as she would be worried about the safety and well - being of her Pokemon.
Maybe Wendy is crying because she realizes she made a big mistake in training her Pokemon. For example, she pushed it too hard and it got injured as a result. She would feel guilty and sad about her actions, which could lead to crying.
Maybe Wendy is crying because her favorite Pokemon got hurt in the fanfiction. It's really sad when a beloved Pokemon is in pain.
Perhaps Boruto cries when he realizes he has made a big mistake that has put his friends in danger. He is a character who values his friendships deeply, and the thought of harming his friends would be a huge blow to him. He might also cry when he witnesses the destruction of the Hidden Leaf Village or when someone he cares about gets seriously injured.
Well, perhaps in a fanfiction, Sasuke could cry for Sakura when he discovers a deep secret she has been hiding. Maybe it's something that makes him understand her on a whole new level, like a hidden pain she has endured all this time for his sake. This newfound understanding could stir such strong emotions in him that he can't hold back his tears.
One possible reason could be that she loses a Pokemon battle that she really thought she could win. In the Pokemon world, battles are very important to trainers, and losing one that she had high hopes for might make her cry.
One possible scenario could be when Lupin has to leave Hogwarts due to his werewolf secret being revealed more widely. He might cry because he has found a sense of belonging there, with his friends and students. He loves teaching and seeing the young wizards grow, and leaving all that behind is heart - breaking for him.
One possible reason could be remorse. Harry might realize that he misjudged Snape all along. Snape had a complex role, and if Harry discovers the truth about Snape's true loyalties and sacrifices, it could lead to him crying out of guilt for how he treated Snape in the past.
It could be when they find out some bad news about the war against Voldemort. Like if they learn of a major defeat of the Order of the Phoenix. Hermione, being highly empathetic and feeling the weight of the situation, breaks down on Harry's shoulder as he is the symbol of hope in their fight and she needs that connection to keep going.
Perhaps in the fanfiction, there's a threat to the Pokemon world. Ash and May team up to face it. During their adventure, they rely on each other, share their hopes and fears. This mutual understanding and support lead them to a realization of their love for one another. And in the end, they plan to get married to build a future together in the Pokemon world.
One possible scenario could be that all their Pokémon friends are part of the wedding. Pikachu might be the ring - bearer, with little ribbons on its ears. Another scenario is that they have the wedding on a beach near a Pokémon Center. Ash could be wearing a traditional tuxedo, and Misty in a beautiful white dress with a water - type Pokémon motif.
One possible scenario could be that Ash betrays May for a powerful Pokemon. Maybe he gets offered a super rare and strong Pokemon but has to cut ties with May to get it. Another could be that May betrays Ash because she is influenced by a rival trainer who convinces her that Ash is holding her back from reaching her true potential as a Pokemon trainer.