☁ — Val

ohhh great question

actually, in Super Smash Bros. Series shows that Kirby is really good friends with Mario characters (like Mario himself and Peach), and in Super Smash Bros. Brawl if you're close to break Peach's cage, Kirby saves her

honorable mention: Luma as well in Rosalina and Luma's trailer of Super Smash Bros. For 3DS/WII U

also not to mention that in the Mario Galaxy movie there's a luma that is clearly a reference to Kirby lol

the only headcanons of Kirby interacting more with Mario characters are Peach and Rosalina.

for Kirby and Peach, i recently see a mod of Super Mario 64 where Kirby is in Mario's place, plus since in the beginning of this game Peach want that Mario comes to the castle because she have bake a cake for him, so would be funny lol— heres a cap of Kirby in Super Mario 64 after credits ending.

and also in Princess Peach: Showtime! there's a level about bake a cake, so i'd like to think that after that Kirby saved Peach, she would bake a cake in form of a star or of Kirby, since Kirby LOVES cakes

I can imagining that Peach would bake this cake for Kirby:

Now with Rosalina: for some reason i think they would sometimes see eachother at space since Kirby is very known for exploring space and has a star that he used to explore it, and Rosalina has a comet to explore as well since she's the princess and PROTECTOR of the cosmos, so they would encounter eachother sometimes? And maybe Rosalina would tell stories for him as well (they would be great friends <33)