HI YES I FINALLY GOT AROUND TO IT !!! I don't think about them a lot but I tried my best !!!

CayRid Headcanons (I LOVE THEM) 

Cater was Riddle’s gay awakening, yes yes, nod nod you will agree with me on this one

It’s also why he says he was so sure he could’ve made it to graduation without getting collared, he knew, Trey knew, I think even Idia from the depths of his room knew. 

Riddle always plays croquet with Cater (and only Cater) because of rule 703 which states that “Anyone who comes in second in a croquet tournament must serve the queen tea the next day” and, obviously, Riddle always wins so Cater is always in 2nd place. (yes the rule is canon it’s in the wiki !)

These tea sessions are lowkey dates, once Ace accidentally interrupted and got double death glared (he didn’t even know Cater had that expression available ?)

Cater loves taking Riddle out to those aesthetic cafes that serve super cute cakes and sweets because he gets a photo op, Riddle gets the sweets and they both get to hang out. 

Sometimes when he’s writing songs for the Pop Music Club and gets stuck somewhere, Cater finds Riddle and uses him as inspiration. 

On that note, Kalim and Lilia notices that the songs they’ve been getting are a lot more pop punk/rock sounding (Cater is not slick especially when he writes about a queen with red hair) 

Riddle and Cater are non PDA kings actually, Riddle finds it embarrassing and highly improper and Cater is not that emotionally open for PDA so they mostly hug or cuddle in their respective rooms since they both don’t have roommates, Riddle’s room is their go to though since it’s huge. 

Riddle is slightly (very) touch starved so he's always touching Cater in some way if they're together, holding his hand, fidgetting with Cater's sleeve, leaning against him

Cater worries that if he fucks up one day he won't be able to stop himself from running away, one night he tells Riddle this and Riddle holds his face and says in the most loving tone ever "If you try and run, I will send every card soldier in Heartslabyul after you until I have you back with me." and Cater has not. Quite recovered from that.

Riddle is surprisingly good at catching Cater off guard, he’s not exactly flirting but he also ain’t not flirting if you feel me ? 

He’ll grab onto the back of Cater’s shirt and tell him softly to meet him for dinner that night and then just leaves, Cater’s so red that Deuce jokes that Riddle’s rubbing off on him a bit too much

They don’t fight much, but when they do, you bet that Trey is their lil messenger boy for when they gotta talk but they don’t wanna see each others faces

If Trey isn’t available (aka when Trey can’t deal with them anymore and threatens to stop cooking if they keep using him as a messenger) then Riddle takes Deuce n Cater takes Ace and then their both the messenger boys. 

Deuce feels like his parents are fighting, Ace feels like his older brother is fighting with his bf who also happens to be his senior, they are not the same. 

i mean, its not against the rules, and with Cater deciding that perhaps this thing doesn't need to go on social media, they just... dont say anything

and they increasingly get up to shenanigans as everyone wonders who is dating who and how to break them up

Chenya comes over, sneaking in and hanging around them. Trey tells him about it. Chenya, who figured this relationship out after observing, decides to keep it secret

Malleus comes over and tells Silver, very sincerely, that he is worried. he is so very confused. he explains the thought process.

"none of us are cheating?"

"forgive me. what?"