Red Hood and Weiss could also have an interesting dynamic. Weiss, coming from a high - society background, might be initially put off by Red Hood's rough exterior. But as they work together against a common foe, she could come to respect his skills and his sense of loyalty to those he cares about.
Another interesting interaction could be between Red Hood and Blake. Blake, with her Faunus background and her own complex views on justice, could have some really deep conversations with Red Hood. They might debate on when it's okay to take extreme measures in the name of justice.
I think the interaction between Ruby and Ben would be really interesting. Ruby is very energetic and has a strong sense of justice. Ben, with his experience of using the Omnitrix to save the day, could share some of his stories with her. They could also have some friendly competitions regarding their combat skills, like who can take down a group of Grimm faster, with Ruby using her Crescent Rose and Ben using one of his alien forms.
Deadpool and Yang could also be really interesting. Yang is tough and has a bit of a hot - headed side. Deadpool would probably egg her on in fights, and she'd either be really annoyed or find his bravado kind of cool. They could have some epic battles together against the Grimm, with Deadpool making inappropriate jokes all the while.
Definitely Iron Man and Ruby. Ruby is young and full of enthusiasm, while Iron Man is a genius billionaire. Their interactions could be really fun as Ruby would be in awe of his technology, and Iron Man would be impressed by Ruby's determination and natural combat skills. He might even see her as a little sister figure and mentor her in some ways.
Naruto and Ruby would be really interesting. Ruby is young and full of energy, much like Naruto. They could bond over their shared enthusiasm for protecting others. Naruto could show Ruby some of his cool ninja moves, and Ruby could introduce Naruto to Crescent Rose. Another interesting interaction would be between Sakura (from Naruto's harem) and Weiss. Weiss is from a wealthy family and is very proper, while Sakura is a strong - willed medical ninja. They could have some really fun arguments and also learn from each other's skills.
Ruby and Church would be really interesting. Ruby is all about being positive and leading her team, while Church is sarcastic and often a bit grumpy. Their different personalities could lead to some really funny exchanges. For example, Ruby might be excited to show Church her scythe, and Church would probably make some snarky comment about how impractical it looks but then be amazed when he sees her use it.
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.
Definitely Joker and Makoto Yuki. Joker is the leader of the Phantom Thieves, very confident and strategic, while Makoto Yuki is a strong and silent type. Their leadership styles could clash or complement each other.
Definitely the interactions between the two versions of Leonardo. The 2012 Leo is more light - hearted in some ways compared to the very serious 2003 Leo. They could have some great moments of leadership clashes and then learning from each other. For example, the 2003 Leo could teach the 2012 Leo some of his more stoic leadership techniques.
I think the interaction between Joker (from Persona 5) and Yu (from Persona 4) would be really interesting. They are both leaders of their respective groups, so they could exchange leadership strategies and learn from each other. Also, Morgana and Teddie would be hilarious together. Morgana's serious yet sometimes clueless nature and Teddie's over - the - top and comical personality would create some great comedic moments.
I think Tucker from Red vs Blue and Yang from RWBY would be an interesting pairing. Tucker is known for his laid - back but confident attitude, and Yang is a strong and fearless fighter. They could bond over their combat skills and exchange stories about their respective worlds.