Sans is another great choice. His laid - back but extremely powerful nature in Undertale would create a lot of interesting dynamics in a Deltarune world. He could befriend or baffle the Deltarune characters. For example, his time - related abilities would be very different from anything in Deltarune, and it would be fascinating to see how he uses them in a crossover situation, like against the Darkners.
Jevil from Deltarune could also be a focus. His chaotic and unpredictable nature would stir things up in the more structured world of Undertale. He might break some of the unspoken rules in the Underground and cause both the monsters and Frisk to have to deal with a new kind of madness. His view of the world being like a 'game' could also be contrasted with the more serious undertones in Undertale.
I think Monika would be really interesting. In DDLC, she has that self - awareness and a certain level of power over her world. If she were in Undertale, her attempts to understand the very different rules of that world would be fascinating. She might try to use her powers to change things, but in Undertale, the concept of determination and the power of the player is very different. So seeing her interact with characters like Flowey, who also has some unique powers and knowledge, could lead to some really intense and thought - provoking scenes.
Toriel would also be an interesting choice. Her motherly nature could be put to the test in the rather unorthodox Family Guy world. She might try to take care of the Griffin family, especially the kids, in her own way. Her interactions with Lois could be really interesting, as they are both strong female characters but with very different personalities. And her fire magic could come in handy when dealing with some of the more dangerous situations in Quahog.
Frisk would also be a great character to focus on. If they were to gain some of Saitama's power, it would completely change their journey in the Underground. They could use their new strength to protect the monsters instead of just trying to find a way out. This would lead to new relationships and storylines. They might be able to stand up to Flowey in a different way, and even change the way the entire Underground views humans.
I think Leonardo and Papyrus would make an interesting pairing. Leonardo's leadership and discipline could contrast with Papyrus' more naive and enthusiastic nature. They could learn from each other, like Leonardo teaching Papyrus some ninja moves, and Papyrus showing Leonardo how to have more fun. Another great pairing could be Donatello and Alphys. They are both the 'tech - smart' characters in their respective universes. They could collaborate on some crazy inventions that combine Undertale technology and Turtle - made gadgets.
I think Freddy Fazbear and Toriel would make an interesting pairing. Freddy is this big, imposing animatronic, while Toriel is a motherly figure. Their interactions could be really cool, like Toriel trying to understand what Freddy is and Freddy being a bit confused by Toriel's kindness.
Frisk and Chica would also be a cool combination. Frisk is all about kindness and determination, and Chica is this animatronic with a bit of a goofy side. Frisk could try to understand Chica's motives and maybe even help her find a new purpose other than scaring people at night.
Ruby and Frisk would be a really interesting pairing. Ruby is full of energy and determination, and Frisk has that unwavering kindness. They could learn a lot from each other, especially in terms of how they approach difficult situations and make decisions.
Ross could be really interesting. Since he's an archaeologist, in a crossover with a show like 'Indiana Jones' (in a fanfiction sense), he could go on an adventure with Indiana Jones. Ross would bring his academic knowledge while Indy would have the practical experience. Their interactions would be filled with Ross trying to over - analyze everything and Indy just wanting to get the job done.
Chiaki Nanami could be an excellent choice. She is the Ultimate Gamer, so if you cross her with a digital or virtual world, there are so many possibilities. She could use her gaming skills to navigate through a new digital realm, like a Matrix - like world. Her calm and intelligent nature would also make her a great character to lead the group in a crossover situation. She could figure out the rules of the new world quickly and help the others adapt.
One idea could be that the characters from Undertale find themselves in the world of Deltarune. For example, Frisk could end up in the Dark World and have to figure out how to get back home while interacting with the Deltarune characters. They might team up with Kris to fight against new threats that are a combination of both universes' villains.