Sora
Sora would confess without planning it. It would probably be on Destiny Island, by the Paupu tree. It may even be while showing Reader how to fight with his wooden sword. He'd "fix" her/his stance just so he could enclose his arms around them.
Riku
Riku isn't really a romantic person, but he would try really, really hard to be romantic. Probably not as romantic he thinks it is. It would probably be on Destiny Island, in the secret place, so he and his crush could be alone. He'd probably be awkward while confessing.
Kairi
Kairi would confess with a cute handmade card that says something cheesy like, "I may be a pure light, but you're the reason why." as well as the favorite flower of her crush. She'd also plan a day of hanging out before she gives them the card and flower. It would probably be on destiny islands, by the paupu tree. They'd watch the stars afterwards.
Namine
Namine draws a comic about her and her crush sharing a paupu fruit. This is the first page that her sketch book opens to in front of her crush. Oops. With a red face, she confesses she likes them.
Roxas
Roxas gives little hints to his crush throughout the day that seem just like niceties. Holding the door open for them, pulling out their chair for them, etc. He accidentally send them a text telling them he likes them, tries to play it off as a true accident until his crush admits they like him back.
Hayner
Hayner acts all tough and macho, but is very different when it comes to Romance. He makes several attempts to tell them in person, but ends up writing several failed notes instead. His crush ends up finding a note that feel from Hayner's pocket. He tries to play it off like that's not his hand writing, but everyone knows it is. Hayner then says to his crush, "If you like me you should just tell me instead of writing a fake note."
Pence
Pence leaves anonymous love notes in his crushes locker. This works for a while before his crush watches from the other end of the hall. His crush then confronts him with evidence that the note has the same hand writing as him. Pence admits it, sheepishly, as he's caught red handed. what a shy boi.
Olette
Olette bakes a beautiful cake with the help of Little Chief. She then invites her crush over to her house, and they both enjoy the cake together. She puts on a romance movie. During the kissing scene, she blushes, looks at him/her and quickly looks anywhere else. She then awkwardly confesses she's never been kisses before, which may or may not be a lie, in hopes her crush gets the hint. If not, she smacks their shoulder and accidentally says, "I'm trying to tell you I like you and want to kiss you!"
Lea/Axel
Lea plans a day of hanging out - playing video games going to McDonald's, walking on the beach. Just before the end he quickly confesses to his crush. If he feels his crush is going to respond in a negative way he plays it off like it was a joke, "You thought I was serious? ha!" Then he goes quiet for a few moments before he asks, "Do you like me for real, though?"
Saix/Isa
Not good at romance stuff. He texts his crush to tell them he likes them. He feels if they don't like them back he can always pretend it was for someone else. He feels like, super awkward as he waits a response. If they take too long to reply he shuts his phone off and pretends it never happened.
Xion :NEW: 4/10/19 (I can't believe I forgot Xion :[ )
Xion drops hints - most are subtle hints like, "Hmm. I wonder what OUR ship name would be." Some are more outward like, "Sora says we'd make a good couple, hahaha." She's shy, but would eventually gain enough confidence to tell them. She'd take them to the Clock Tower to confess because that's were all the people that are important to her tend to like.
Terra
Terra tests the waters first. It will be like his knee touching theirs for a moment. If he does it a few more times and the person seems okay with it, he will 'stretch and rest his arm' behind their seat. If things are still good, he manages to bring up that he needs advice to ask his crush out. He then uses the advice his crush gives him to ask them out.
Aqua
Aqua accidentally confesses while bandaging up her injured crush. She rambles until it slips out she really likes them and doesn't want to see them hurt. She turns red and tries to back track, only to fumble with her words and she feels more awkward.
Ventus
Ventus is shy. He first asks his crush to the High school dance. If they agree, he slips out that he is relieved because he was afraid they'd say no and that'd make him sad because he really likes them and - Oops. He tries to avoid them the rest of the day. He texts them later that night with a long, senseless apology.
..::Author's note::..
I hope none of the characters are too OOC.
Feel free to request head canons or stories! :3

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Kingdom Hearts x Reader
RomanceReader inserts/Head Cannons for Kingdom hearts. May your heart be your guiding key.