How he asks you out

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Draco-
It was fifth year when he finally mustered up enough courage to ask you on a date though he didn't really ask you at all.
"Y/n, come on a date with me this Christmas holiday to Paris." He had said leaving you blank faced with shock.
Needless to say you went on the date and had a lovely time.

Blaise-
It was the last day fifth year when he had left a note on your desk that read;
Dear Y/n,
You probably won't want to join me but I was hoping I could take out for dinner next week.
If you'd like to go then owl me, oh and wear something nice.
You gladly accepted and went to dinner with him, and he was surprisingly sweet.

Cedric-
At the end of fifth year he asked you in a date and you agreed in a flustered way including a lot of blushing from embarrassment.
He ended up not having any plans at all since he thought you would have rejected him so the two of you just took a nice walk and stopped for lunch, but you wouldn't have changed a thing.

Harry-
It took Him three years to ask you out, in your third year and his fourth.
It was around time for Slughorn's Christmas party and Harry had asked you with broken nervous sentences. You accepted with a smile and the two of you had an awkward first date to say the least but it was enjoyable.

Ron-
He had asked you out on accident during transfiguration class months after meeting you. You agreed, thinking it was cute how flustered he had become after asking and he took you to watch a professional quidditch team and the two of you stopped at Honey Dukes after and both got a new treat for the other person to try.

Fred-
After a month or so of him fallowing you around he pulled you aside and asked you out. You agreed after thinking about the offer for two days.
He brought you to the burrow and introduced you to his family.
How that was a first date, you don't know but Molly seemed to love you so that was good.

George-
One day after setting up a prank against Harry and Ron George kissed your cheek and asked you out. You agreed and the two of you skipped school to go to Hogsmeade and you two also bought some new prank supplies while you were out.

Newt-
He had asked you out over a note one evening during fourth year. You accepted and over that weekend he took you into the forest and rambled about all the creatures in the forest and the ones he had studied while you took a few pictures here and there.

Theseus-
He asked you out in sixth year but you were the one to come up with the idea. Since you were raised with Muggles you took Theseus roller skating, and you had to teach him how to actually do it but you enjoyed the whole thing either way.

James-
He asked you out at the end of sixth year by accidentally sending a howler to the Hufflepuff table during lunch. You were embarrassed but after lunch when he apologized you agreed to the date before walking off to Herbology class.

Sirius-
He asked you out over the summer before sixth year.
You were just minding your own business as he came waltzing into your room and sat beside you asking you to go on a date with him and after being around him for a whole school year you just agreed.

Tom-
You asked him out actually.
It was the beginning of seventh year and the two of you were walking to Defense against the dark arts when you asked him out on a study date. He didn't respond and looked utterly shocked before finally agreeing at the end of the day.

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