A very popular pairing is Pikachu and Eevee (in a more anthropomorphic sense in fanfiction). Since they are both very cute and popular Pokemon, writers often explore their relationship in a high school setting. They might have little adventures together, and their 'friendship' could potentially turn into something more. Another one is Tracey and Lillie. Tracey's artistic side and Lillie's gentle nature can create a sweet and harmonious pairing in Pokemon high school romance fanfiction.
One popular pairing could be Gohan and Rias. Their personalities are quite different, with Gohan being more reserved and Rias being a strong - willed devil. The contrast between their powers and backgrounds could create an interesting dynamic in the fanfiction.
Another popular character could be Gary. He could be the school's star student, always competing with others to prove his superiority. His rivalry with Ash could be carried over into the high school environment, creating some intense and exciting moments in the fanfiction.
Percy and Annabeth are a very common pairing. Their relationship from the original series can be further explored in high school settings in fanfiction. They already have a strong bond, and in high school, they can face new challenges together like dealing with normal high school drama while being demigods. Another common pairing is Nico and Will. Their different personalities, Nico being more brooding and Will being more upbeat, create an interesting dynamic in a high school romance context.
A very common pairing is Loki and Thor. In a high school setting, Thor could be the popular jock type while Loki is the more brooding, artsy kid. Their brotherly dynamic would be interesting to explore in this context. Another popular pairing could be Loki and Natasha Romanoff. She might be the one to see through Loki's tricks and they could have a sort of cat - and - mouse relationship that slowly turns into something more. And of course, Loki and Tony Stark could be paired up. Stark's sarcasm and Loki's mischief would make for some great banter.
Thranduil and Legolas' mother is another pairing that appears in some fanfictions. Since not much is known about Legolas' mother in the official lore, it gives fanfic writers a lot of room to create their own stories about Thranduil's relationship with her, often adding a touch of mystery and historical depth to the romance.
Issei from High School DxD is often a popular character in these crossovers. His perverted yet determined nature can create some interesting interactions when combined with the Pokemon world. Maybe he tries to use his charm on female Pokemon trainers or gets excited about rare Pokemon in a way that's similar to his reactions to girls in the original series. Another popular character could be Pikachu. Pikachu's cute appearance and powerful electric attacks make it a favorite, and seeing it interact with the characters from High School DxD can be really entertaining.
May is often a very popular character. She's enthusiastic about Pokemon contests and has a great character arc. Drew is also popular, as he serves as a rival and has his own charm. And of course, Ash, who is always involved in some way in the Pokemon world and often has interactions with the Contestshipping characters.
Yugi and Ash could be an interesting pairing. Yugi's strategic mind from Yu - Gi - Oh duels could help Ash in his Pokemon battles. And Ash could introduce Yugi to the world of Pokemon training. Another pairing could be Kaiba and Gary. They both have that competitive streak. Kaiba might be intrigued by Gary's skills as a Pokemon trainer and Gary could be interested in Kaiba's high - tech Duel Disk.
Ben and Issei would be an interesting pairing. Ben is used to being a hero with his Omnitrix, and Issei has his own journey of becoming a powerful devil. They could learn from each other's combat styles. Ben could show Issei how to use his alien forms' unique abilities in battle, and Issei could teach Ben about the world of devils and the importance of relationships in his world.
A popular pairing could be Naruto and Draculaura. Their personalities are quite different, with Naruto being the energetic ninja and Draculaura being the sweet vampire. The contrast between them could create some really interesting relationship dynamics in the fanfiction.