I think pairing Harry Potter with Jack Skellington would be really interesting. Harry is used to the magic of the wizarding world, and Jack is the master of Halloween Town. Their different approaches to magic and problem - solving would create a lot of interesting interactions. For example, Harry could teach Jack about some of the more traditional forms of magic, while Jack could show Harry the unique and spooky magic of Halloween Town.
Ron and Oogie Boogie could be a very unexpected and interesting pair. Ron is often a bit clumsy and food - loving, while Oogie Boogie is a villainous and spooky character. Ron could be both terrified and intrigued by Oogie Boogie. Maybe Ron gets caught by Oogie Boogie, and through his own bumbling attempts at escape, he manages to outwit the villain in a way that no one expected, using his knowledge of wizarding world pranks and spells.
Hermione and Sally would make an amazing pair. Hermione is highly intelligent and loves to learn, and Sally is a very creative and resourceful character in Halloween Town. They could bond over their knowledge of different kinds of magic. Sally could share with Hermione the secrets of the potions and spells she uses in Halloween Town, and Hermione could offer Sally insights into the more academic side of magic, like the history of magic that she has studied at Hogwarts.
Ron and Nick Burkhardt would be an exciting combination. Ron has his loyalty and his skills with magic, while Nick has his detective skills and his ability to handle Grimm situations. They could go on adventures together, with Ron using magic to help Nick in tight situations and Nick using his street smarts and Grimm knowledge to guide Ron through the non - magical aspects of the Grimm world.
Hermione Granger and Sakura Haruno could make a great pairing. Hermione is known for her intelligence and thirst for knowledge, and Sakura is a smart and determined kunoichi. They could exchange medical knowledge, Hermione's knowledge of potions and Sakura's ninja medical skills. They could also bond over their shared experiences of being part of a team and having to prove themselves in a male - dominated environment.
Ron Weasley and Joey Wheeler would be a fun pair. Ron is often the more laid - back and comical sidekick in Harry's adventures. Joey is also a bit of a hot - headed and humorous character in Yu - Gi - Oh!. They could get into all sorts of misadventures together. Maybe they start a small - scale Duel Monsters tournament within Hogwarts and cause a bit of chaos as they try to figure out the rules and make it work in the wizarding world.
I think Sirius Black and the Dowager Countess would be a hilarious pair. Sirius is a bit of a rebel, always defying the norms of the wizarding world. The Dowager Countess is set in her ways and very proper. Their interactions would be full of comical misunderstandings. Sirius might accidentally use magic in front of her, and she would be both shocked and intrigued, trying to maintain her dignity while dealing with this strange new phenomenon.
Definitely Harry Potter and Twilight Sparkle. Harry is used to dealing with dark magic and danger, while Twilight is all about knowledge and friendship. Their interactions would be really cool. Harry could teach Twilight about some of the more dangerous aspects of magic, and Twilight could show Harry the power of friendship in Equestria.
Ron Weasley and Four Arms from Ben 10. Ron is known for his loyalty and his skills in wizard chess. Four Arms is a strong and powerful alien. Their personalities are quite different. Ron might be a bit intimidated by Four Arms at first, but as they get to know each other, they could form an unlikely but strong team. Four Arms could help Ron in physical battles, and Ron could use his wizarding skills to protect Four Arms from magic - based attacks.
I think Obito and Hermione would be an interesting pair. Hermione is all about knowledge and Obito has a deep understanding of his ninja world. She could be fascinated by his sharingan and his unique abilities. He could learn from her about the complex magic system in the Harry Potter world. They could work together to solve mysteries that involve both ninja techniques and magic, like unravelling a curse that has both magical and chakra - based elements.
Harry Potter and Sans would be an interesting pair. Sans is known for his laid - back yet perceptive nature in Undertale. Harry, with his burden of being the 'Chosen One' in the wizarding world, could learn a lot from Sans' non -chalant attitude towards life. They could also share their experiences about dealing with difficult situations. Sans could teach Harry some of his shortcuts in the Underground, while Harry could show Sans some of his magic tricks.
Obviously, Harry Potter himself could be a main character. He has the courage and magical ability to handle the strange and spooky situations in Halloween Town. Hermione Granger would also be a great main character as she has the knowledge to figure out the unique magic and lore of the town. Ron Weasley could be there too, providing some comic relief and loyalty. Another possibility could be Luna Lovegood. Her out - of - the - box thinking would be very useful in a place as strange as Halloween Town.
Definitely Buffy and Harry. They are both the main heroes in their respective stories. Buffy's physical combat skills and Harry's magical abilities would make for a great combination. They could learn a lot from each other and face challenges together.