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.
The interaction between Mitsuru and Ann would be fascinating. Mitsuru is a very composed and refined young woman who is also a powerful Persona user. Ann, on the other hand, is more free - spirited and bold. They could have some great conversations about their different outlooks on life, as well as how they use their Personas in combat and in their daily lives.
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.
Bayonetta and Joker would be really interesting. Joker's strategic mind and Bayonetta's fearless fighting style could create some great synergy or interesting clashes. They might learn from each other's combat techniques and ways of approaching challenges.
The interaction between Yu Narukami from Persona 4 and Makoto Yuki from Persona 3 could be really interesting. Yu is a very calm and perceptive leader, while Makoto has his own sense of leadership. They could share their experiences in leading their respective teams and learn from each other.
Chie and Ann would be an interesting pair. Chie is into martial arts and Ann is a model. They could have a great dynamic where Chie is in awe of Ann's fashion sense and Ann is impressed by Chie's physical strength. And they could learn from each other, like Ann teaching Chie some modeling poses and Chie teaching Ann some self - defense moves.
Chie Satonaka from Persona 4 and Ann Takamaki from Persona 5. They both have strong personalities and are very passionate about their causes. Chie with her love for kung - fu and Ann with her modelling career. They could bond over their determination and share their combat skills and life experiences with each other. It would be fun to see how they interact in a crossover scenario.
Yu Narukami and Joker would be an interesting pairing. Yu is the calm and collected leader of the Investigation Team, while Joker is the charismatic leader of the Phantom Thieves. They could exchange ideas about leading their respective groups and how to deal with the Shadows. Their different fighting styles and Persona abilities could also make for some great team - up moments in battle.
Yukari (from Persona 3) and Chie (from Persona 4). Yukari is very outspoken and has a bit of a sarcastic side, while Chie is energetic and a bit of a tomboy. Their different personalities could lead to some really fun and comical interactions, especially when they're facing Shadows together or just hanging out in the school setting.
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.
Makoto Naegi from Danganronpa and Yu Narukami from Persona. Makoto's determination and leadership skills could pair well with Yu's calm and collected nature. They could work together to solve the mysteries that occur when their worlds collide.
Ruby and Yu Narukami. Ruby is young and full of energy, always eager to fight for what's right. Yu is a calm and collected leader. Their different personalities would make for an interesting dynamic. Ruby could learn from Yu's more methodical approach to problem - solving, while Yu could be inspired by Ruby's unwavering determination.