If you could pair up Key with any of the characters in your fic in a shipping sense, including the OCs, who would it be and why?
Ooohhhhh, never thought I'd be asked a question like this!
Never thought I'd see the day *wipes tear from eye*
Anyway, given how Key is still stuck in survival mode and still contemplating on the question of whether or not she can return home, she isn't going to be at all focused on romance. Friendship maybe, but anything deeper is out of the question. However, if circumstances were to change, if her perception of what choices are available to her have become clear, I think I'll have to go with the somewhat cliche route.
My favorite fox boy, Cameron Norton.
Their banter was really funny and fun to write and read during the prologue arc. They have a good, established relationship, they certainly trust each other, and have seen each other at some of their most vulnerable moments. They know a certain extent of each others hopes and dreams (although it wouldn't hurt for more heart to hearts if they were to ever pursue a romantic relationship). Furthermore, it would probably go down a friends to lovers type of story. Perhaps Cameron would make teasing, joking comments in his emails to Key about "dating" and maybe Key responds in kind. These jokes gradually develop into something true and real when they eventually move out of emails and either meet up face to face or actually call each other.
However, while their relationship is very positive and I have feeling they would bring out the best in each other, I think it would be kind of... unhealthy to say the least. From what we have seen, Key is isolated. Very isolated. Sure, she's on amicable terms with the Housewardens and is slowly accepting the found family vibe with the custodians (but still very guarded), but that doesn't mean she's truly ready to accept new relationships. Except for Cam. He alone is the one true friend Key has at the moment of writing this. Yet, if there is a romantic relationship at this moment of the story, Key would be using Cam as a crutch and not venturing outside of her relationship with him.
I think I would do a disservice to both key and Cam in the story if I were to treat their bond as such.
So, maybe in the future after Key's arc has long since finished, but not definitely a priority at the moment.
As for canon relationships...
Again, at the moment, there isn't any need for romance. Key is still very much a member of staff and while she is basically around the students' age, there is still an inherent power imbalance that is somewhat equalized by the fact that she's only a secretary/janitor. And she's also magicless.
But... if we were to rid ourselves of such important facts... Maybe someone who's fun? Someone who's willing to bring Key out of her shell, to give her reason to think of Twisted Wonderland as her home, and to be as spontaneous and fun as she is. Who doesn't listen to rigid rules without question and creates a fun sort of chaos that will make Key laugh.
Someone like... I don't know, Floyd?
(Love me some crackships when I was younger, so I'm bringing that out here hahaha)
Wouldn't it be funny if the endgame romance (not that there will be endgame romance in Caged Birds) was Floyd and Key? How would that work... Key'd? Flokey? Ohhhh, Flokey could work heheheh
Do you ship Key with anyone, perchance?
Thanks for the question and I hope that you have a wonderful day! :D