Harry Hook falling for the daughter of Rapunzel and Flynn: (short and sweet)
Harry would fall first, but you’d fall harder.
He’d in the enchanted forest not long after finding Ben as a beast. Jane would have just turned the king back into a human with the water from the enchanted lake- Harry would go to comment on the absurdity of something as simple as water holding so much power, but he’d..pause- as he sees you stood not too far behind Jane, and gosh, would his eyes simply light up.
“Well, well, well…I’m- Harry hook.” He’d smirk, pushing Jay out of the way to get, the hand not holding his hook coming to his chest as he stops infront of you. “And you- my little duckling..are..ravishing.” Harry would mutter breathlessly, eyebrows lifting as he shamelessly looked you up and down, Scottish accent thick and playful.
You, not having a clue he’s flirting- would smile widely at him. “My father took my mother to a tavern called The Snuggly Duckling when they met! It’s crazy you called me that!” You’d laugh, walking towards him, your nose and eyes scrunched with amusement and wonder as you practically emit sunshine. “I’m—y/n—Fitzherbert!”
From then, he’d be hooked. No pun intended. He’d spend the rest of the time fighting Audrey with you, flirt and laugh with you. You’d be the only person he gives a proper goodbye too when he believes Mal and Ben won’t allow anyone to enter or exit the isle ever again- and you’d be the first person he seeks when the barrier gets brought down, joining the two sides together.
You’d dance together- talk, you’d give him your own personal tour around the school grounds and even show him the enchanted lake. You’d show him your paintings, let him try to paint something himself (which ended with a bad painting of the sea on your wall near your bed) and he’d teach you how to handle a sword, which has ended with him having a couple of cuts and marks on his hands and face- which you’ve profusely apologised for countless times. You’d bake together and you’d teach him how to play chess- he’d let you meet the other men on his crew- and you’d naturally…get closer. More flirty as time went by..and you’d realise after a couple of days that- Harry’s kinda hot??
It takes him less than two months to ruin the flirty “friendship” and ask you on an official date- on a pirate ship he happened to “find” in auradons docks of course. You’d both drink rum and dance and have a picnic on the deck. You’d press an innocent peck to his cheek which would ultimately end with his tongue down your throat.
A couple of months into your relationship- not long after he asked you to be his official girlfriend, you’d take him home on your mothers birthday- to corona and you’d let him meet your parents and see the floating lights, Rapunzel likes him from the start- says she reminds her of the way Eugene used to act with her- which is exactly why Flynn himself would be..hesitant, at first. His sweet, sunshine loving, daughter? With a pirate who wears- eyeliner?..But- he’d soften up within an hour of having conversation with him over tea; still with his suspicions though.
Harry would admire the lanterns when they’re set off later into the night, of course, but he’d also not be able to take his eyes off of you- not for more than a second, with this soft, sort of relaxed look on his face. Something your father recognises rather quickly as the same look he gave his girl on a boat less than two decades beforehand. This causes that suspicion to immediately dissipate, leaving behind only relief that your in good hands.