Gandalf and a wise old dragon. Gandalf could exchange magical knowledge with the dragon. The dragon might offer its insights on ancient magic, and Gandalf could teach the dragon about the different forms of magic in Middle - earth. They could also work together to solve some big problems in both worlds.
Definitely Legolas and Will Turner. Legolas with his amazing archery skills could teach Will some new techniques, and Will could show Legolas the ropes of being a pirate. They both have a sense of honor and loyalty, so they would make an interesting duo.
One idea could be that the dragons from Wings of Fire find themselves in Middle - earth. They might get involved in the War of the Ring, using their unique dragon abilities to turn the tide of battles. For example, their fire - breathing could be a great asset against the orcs.
I think Lucy from Narnia and Frodo from LOTR would make an interesting pairing. Lucy has her own kind of innocence and faith, which could be a contrast to Frodo's burdened and determined nature. She might be able to offer him a different perspective on his quest, and he could show her the more complex and dangerous world of Middle - earth.
I think Naruto and Frodo would be really interesting. Frodo has this burden of the One Ring and Naruto has his own struggles with the Nine - Tailed Fox. They could bond over their heavy responsibilities and Naruto could use his skills to protect Frodo on his journey.
Naruto and Aragorn would be an interesting pairing. Naruto is a young hero full of energy and determination, while Aragorn is a battle - hardened and noble leader. They could learn a great deal from each other. Naruto could show Aragorn his unique ninja skills, and Aragorn could teach Naruto about leadership and honor.
Neptune and Sora from Kingdom Hearts would make an interesting pair. Neptune's carefree and fun - loving nature could contrast well with Sora's more heroic and determined personality. They could go on an adventure together, with Neptune showing Sora the wacky and unique aspects of the Gamindustri world while Sora teaches Neptune about the different Disney - inspired worlds he has visited.
Well, Gateau could be paired with a tough, no - nonsense character. Gateau's flamboyant style and the other character's more serious demeanor would create a great dynamic. They could have some hilarious banter while also being a formidable team in combat. Also, Tira could be paired with a character who has a very different moral code. Tira's innocence and the other character's more jaded view of the world could lead to some interesting character development for both as they influence each other throughout the story.
Shirou from Fate and Kiba from DxD could team up. Shirou's selfless desire to protect others combined with Kiba's sense of justice as a former Exorcist turned Devil would make them a formidable duo. They could share their combat techniques and learn from each other while fighting against the various threats that lurk in a world where the two universes have collided.
If crossed with Buffy the Vampire Slayer, Buffy and Rose would make a formidable pair. They both have a no - nonsense attitude when it comes to fighting vampires. They could bond over their shared experiences of protecting others. And Spike from Buffy could be paired with some of the more edgy vampires from Vampire Academy. Their different takes on being a vampire could lead to some intense and humorous interactions.
A really interesting pairing could be Hermione and Tyrion. Hermione is extremely intelligent and well - read, and Tyrion is also very clever and a great strategist. They could share their knowledge of different forms of politics and magic. Another good pairing would be Harry Potter and Jon Snow. Both are heroes in their own right, with a strong sense of justice. They could learn from each other's experiences of growing up as outsiders and leading in difficult situations.