Small note:
Please don't attack me for Ron asking Lavender for help and say "Ron would've asked Hermione."
I honestly believe that Ron and Lavender would have stayed friends after their breakup. Lavender deserved better and is a human with feelings. Not a psycho or stalker who craves attention. Thank you for listening and enjoy the story.
Harry:
"Y/n, I believe that it is outrageously stupid of me to not take you on a date yet. We've been together 2 months and I think tonight is the night I make things special!"
You'd never think in a million years that he would go to Draco Malfoy for help.
"Draco, I really need your help. Not for me but for Y/n. I am in love, I would do anything for this amazingly beautiful-"
"Shut up, Pottah. I'll be there to help around 7:00pm."
He would ask Hagrid to cover for Him, you and Draco and would sneak out with you to take you to a carnival.
Draco would secretly tag along to help Harry make sure you're having a good night. Draco would probably rig a game or two if he's bored or if he just wants to embarrass Harry. But at the end of it all you had fun and Harry won you 6 prizes. Draco got himself one of those 6ft long snake plushies.
Ron:
"Hey, y/n. So remember when I asked you to be my significant other because I love you and stuff? Well I feel like you deserve something more than that. Let me take you out tomorrow night."
"LAVENDER I NEED YOUR HELP!"
"Relax, what's going on?"
"I need you to help me plan this date I promised, Y/n."
Lavender is the queen of decorating.
She convinced everyone in Gryffindor to help set up the common room as one of those fancy dinner tables. When you walked in the room was rearranged and everyone was dressed up as waiters and waitresses because they wanted to watch everything go down. It was the cutest thing. Harry had on those weird hats. (You guys know what I'm talking about right?)
Draco:
"Y/n, I give you all my attention, love, affection, money, time, compliments, presents and gifts, and I would give you the skin off my back if I could. But you deserve so much more than what I'm giving you. Meet me at the Astronomy tower tonight."
Draco asked hid father to convince the teachers to let you guys go to the town for the night.
He hooked up the best table and made sure it was a booth in the back and not the tables in the center. (They give me anxiety, and I know very well it gets you guys nervous too lol.)
He would be a classy man. Probably pay everyone to leave the restaurant just so he can dance with you in private.
"You make me benevolent, Y/n."
Fred:
He would convince his dad to let him use the car to go to the muggle world.
"Y/n, I got tickets to, um- Muh-laney Mar-tiny..ez?"
It would be his first time going to a muggle concert. He ends up loving the energy of the people there.
"CRY-BABY! CRY-BABY!!"
He'll probably buy you merch. He'd definitely dance like a maniac with you in the crowd.
Definitely buys the CDs and those tiny DVD radio things so he can play in at home or at Hogwarts.
"I may not have a lot of money or the fanciest things in the world. But I am glad I own one thing that's worth more than gold."
George:
"Y/n, have I ever told you how extraordinarily lovely you are?"
"Fred, this has to be bigger than fireworks!"
He would skip classes for a week to set this up for you. He would go to Neville to ask what the perfect flower would be to give you. "Neville, this has to be as rare and beautiful as Y/n. It has to be worth how much Y/n is to me."
"And how much is that, George?"
"The world."
He would leave a whole trail of these leading to the lake.
(Neville and George working together as friends is high-key cute)
Neville:
Y/n, can you do me a favor and meet me at the greenhouse tonight?"
This adorable bean would but in all his time and effort and get help from a few friends (most likely Luna) and obviously with his privileges that he get's from Professor Sprout, he would decorate the greenhouse with the prettiest flowers and plants with white lights and a table in the middle with food. The definition of a real gentleman.
"I might not be the toughest or strongest man. I know I'm a squib. I let my grams down...and my parents. But I will keep fighting until my knees give in when it comes to you."
Tom:
"Y/n, let me take you out as an apology for almost killing you when you hugged me."
He would read a book about dates and study it all day.
He wouldn't know where to take you and probably just overly decorate the Slytherin common room. It would look nice and fancy though.
"Ok- so take a seat....NOW."
He would give you a necklace with a gem in the middle.
"Are you amused?"
You would convince him to dance with you.
"I know I'm not the best when it comes to- well this. But I do highly appreciate your existence, and I lOuve you?
Questions what he said afterwards.
Cedric:
"Do you want to do something exciting tonight?"
He'll sneak you guys out to Honeydukes.
Buy every and any candy you want.
"Hey, Y/n, look! My tongue is red from the lollipop, and I noticed yours blue."
He would say things like "You're sweeter than all of these sweets combined."
"What I'm saying is we should make our tongue's purple."
Looks like a whole kid while eating his candy. It's cute.
"You have no idea how happy I am when I'm with. I really hope I was able to make you feel what I feel."
Oliver:
"So, I cancelled Quidditch practice. Erm, because I wanted to spend some time with you."
You could literally see in his face that he was battling a wave of emotions between you and Quidditch.
You asked if he wanted to go on the Quidditch field to make him feel better.
This man said no for the first time ever. Strong.
You guys took a walk around the halls instead and were acting like lunatics.
He did one of those backflips off the wall.
"Let's go prank Mr. Filch."
"If I had to choose between you and Quidditch..."
"You would choose me?"
"Nope. Quidditch."
Seamus:
"Y/n, go on a date with me if I'm wrong but, I'm ugly right?"
"I guess that means no date."
You did not have to shoot him down like that.
You did end up laying in bed with him and listening to his corny jokes.
"Why does Peter Pan always fly? Because he NEVER-LANDS!"
You kicked him a good 3 times.
"How did I get so lucky with someone as beautiful as you?"
Dean:
"Y/n, thy shall ask if you are permitted to play....JUST DANCE!"
*dramatic gasp*
"My Dear, you look ravishing this evening."
"I'm wearing sweat-pant."
Probably just hangout with him and a few of the Gryffindor boys in their rooms.
Makeout infront of the others just to disgust them.
"You are so amazing, I bet you don't even realize your worth, huh?"