The interaction between Naruto and Rukia could be great. Naruto's exuberance and positive attitude could contrast with Rukia's more serious and stoic nature. They could bond over their loyalty to their friends. Maybe Naruto could make Rukia laugh with his silly antics, and Rukia could teach Naruto some of the more refined aspects of combat from the Soul Society.
Definitely Naruto and the Little Sisters. Naruto has a soft spot for those in need, and the Little Sisters are in a very vulnerable position. He would probably be very protective of them, and the contrast between his energetic and positive personality and their rather timid and strange existence would be fascinating.
Sasuke and Zoro could have some cool interactions. They are both very strong and somewhat brooding characters. Zoro might be interested in Sasuke's Sharingan and the power it holds, while Sasuke could be intrigued by Zoro's three - sword style.
Definitely Naruto and Twilight Sparkle. Twilight is all about knowledge and magic, and Naruto has his own unique ninja powers. They could have really deep conversations about how their powers work and share knowledge. Maybe Twilight could try to study Naruto's chakra system using her magic, and Naruto could be amazed at how Twilight's magic can do things like levitate objects and create spells.
Definitely Superboy and Wolverine. Wolverine's gruff and experienced nature against Superboy's more idealistic and young hero self would make for some great dialogue and action scenes.
Definitely Sans and Jevil. Sans' laid - back yet perceptive nature combined with Jevil's chaotic and unpredictable personality would make for some really interesting exchanges. Sans might try to understand Jevil's view of the world, which is so different from his own in Undertale.
I think Negi and Iron Man would have great interactions. Negi is a young wizard full of potential, and Iron Man is a genius with his high - tech suits. They could probably learn from each other, like Negi learning about technology from Iron Man, and Iron Man getting inspired by Negi's magic for new suit designs.
Ichigo and Maka would be really interesting. Maka is all about order and the pursuit of making her weapon, Soul, into a Death Scythe. Ichigo, on the other hand, has his own code as a Soul Reaper. They could clash over their different ways of dealing with souls and the afterlife, but also learn from each other.
Ichigo and Edward would be really interesting. Ichigo, with his brash and head - on attitude, would contrast with Edward's more brooding and cautious nature. They could have debates about what it means to be immortal, as Ichigo has his own reasons for being immortal that are different from Edward's vampiric immortality. Also, Ichigo's combat skills could be something that Edward admires and wants to learn from, while Ichigo might be interested in Edward's mind - reading ability.
I think Naruto and Weiss would have some great interactions. Weiss is from a high - class family and is very proper, while Naruto is this rough - around - the - edges ninja. Their clash of cultures could lead to some really funny and also some really deep moments. Maybe Weiss could teach Naruto about the importance of elegance in combat, and Naruto could teach Weiss about the value of hard work and determination from his own experiences growing up.
The interaction between Iron Man and Kakashi would be really interesting. Kakashi is a very intelligent and experienced ninja, and Iron Man is a genius inventor. They could exchange ideas about combat strategies and knowledge from their different worlds.