Richard. His business acumen and knowledge of politics could be very useful in the Stark world. He could advise the Starks on economic matters and trade deals. He might also be intrigued by the feudal system and try to find ways to improve it, while at the same time sharing some of his wisdom about leadership and education with the Stark children.
Another likely combination could be Rory, Jess, and a new character. Jess has a special place in Rory's heart. Adding a new character to the mix could introduce a fresh perspective. The new character might be someone who challenges Rory's feelings for Jess and vice versa. The threesome could be a way to explore how Rory's past love for Jess still lingers while she's also open to new experiences with this new person.
Rory could fit in as a strategist. Her academic achievements and quick - learning ability would make her valuable in planning battles. For instance, she could analyze the patterns of the enemies like Loki or Ultron and come up with effective counter - strategies.
She would probably interact with Tony Stark in an interesting way. They are both very intelligent. Rory might be in awe of his technology at first, but then start debating with him about the ethics of some of his inventions. With Captain America, she could learn a lot about leadership and loyalty, and in return, she could teach him about modern literature or something.
Frankie Stein might also interact well. Frankie is always curious about new things and how they work. The FNAF animatronics with their mechanical and somewhat mysterious workings would be right up Frankie's alley. Frankie would probably try to study them and figure out how to make them less menacing, or at least understand their purpose.
Luna could also be a great character to interact with Casper. Given her love for all things cool and different, she would probably be really excited to meet a friendly ghost. She might even write a song about their encounter.
I think Quinn and Black Widow would be an interesting pair. Quinn is used to being in a position of power and popularity in the Glee club, and Black Widow is a strong female character in the Avengers. They could have some really cool exchanges about strength and femininity.
I think Sakura from Naruto and Stella from Winx could interact a lot. Sakura is a strong - willed and intelligent kunoichi, and Stella is a confident and powerful fairy. They could have some really interesting conversations about their respective worlds, like comparing the medical ninjutsu in Naruto's world to the healing magic in the Winx world. And they might also get into some friendly rivalries while training together.
Definitely Ruby Rose and Master Chief. Ruby is the main character in RWBY, full of energy and determination. Master Chief is a well - known and iconic figure in Halo. Their different personalities and combat styles would create an interesting dynamic. Ruby's quick - thinking and agility could pair well with Master Chief's stoic and strategic approach in battles.
Bloom and Iron Man could be likely to interact. Bloom is a powerful fairy with strong leadership qualities, and Iron Man is a genius inventor and leader in the MCU. They could both exchange ideas about leadership and power, and maybe Bloom could teach Tony a thing or two about magic. Another pair could be Stella and Thor. Stella loves fashion and luxury, and Thor is from a royal background in Asgard, so they could bond over their love for grandeur.
Hermione would be a great candidate. Her thirst for knowledge and eagerness to learn about different forms of magic would make her very interested in Dante Vale and his skills. She would probably bombard him with questions and they could have long discussions about magic.