Thank you for asking, sweetie! I love the bunch of buys you requested!
Askbox is now closed for MTL!
MOST
Kiyoshi
Takao
Ootsubo
Hyuuga
Kasamatsu
Wakamatsu
Imayoshi
LEAST
They don’t really have that much difference in the ranking tbh! Like I imagine half of them most likely say “I love you” to their s/o with ease, while the other half might have a small prerequisite of some sort for saying “I love you”.
Obviously they all would have to love their s/o first before saying it out loud, but Kiyoshi, Takao, and Ootsubo would say it first. All three, I feel, have a great sense of self-awareness and are able to acknowledge the facts, including the fact that they have deep feelings for their s/o. Takao especially has no inhibitions whatsoever in confessing that. Kiyoshi and Ootsubo are probably in too deep to be embarrassed lol
As for the rest, the prerequisite I mentioned will be discussed in the following. For Hyuuga, Kasamatsu, and Wakamatsu, I think they would acknowledge their feelings early on, but would be too shy to say it out loud until they’re just so full of love it physically hurts them and they blurt it out. I think Wakamatsu in particular would be looking for signs that his s/o feels the same, so maybe the s/o needs to send him hints.
Imayoshi, the meticulous bastard (jk I love him)—the prerequisite for him is that he has to know absolutely that his s/o is in love with him. Expect him to execute moves designed to make his s/o smitten, until there’s just no way his s/o doesn’t love him. You may call it manipulation, but he likes to call it a warrant. Only after that will he say those words first.
I love your reasoning! You have a great grasp of these characters. Thanks for the event!