How they ask you out

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Regina:
It wasn't really asking. More like demanding. You worked for her as a maid and she grew to like your fiery personality.
"Y/N, we'll be having dinner tonight at 8 o'clock. Don't be a minute late" she announced as you finished mopping the floor.
"I don't remember you asking" you sarcastically remark, causing her blood to boil slightly.
"That's because I didn't ask"

It took a lot to make Regina feel guilty but she did feel a little bit of guilt after she ordered you to go on a date with her.
"Y/N...I'm sorry for ordering you to have dinner with me..." she quietly spoke. You could barely make out her words and you were so shocked you almost thought she didn't say it.
"Would you like to have dinner with me?" She asked looking at you. For the first time you didn't see the evil Queen. You saw Regina for who she use to be. A poor girl who was scared and heartbroken. You agreed under the condition that you got to pick the food. After a while, she agreed.

Emma:
After she broke the curse she was open to having a relationship. But you actually asked her out. Knowing she would take her time asking. You approached her in Grannys while everyone was talking and Henry was with David.
"Hey Emma. I need to ask you something" you admitted and she put her drink down and looked at you.
"Fire away" she smiled. You took a deep breath and prayed she wouldn't say no.
"Wanna go on a date sometime?" You asked. It completely shocked her and Snow who was listening to your conversation. It took her a couple of seconds to process the question but once she did she started to smile. She nodded and hugged you. It wasn't your first hug but it was the most memorable one. It lasted awhile and you were sure people were watching and you honestly didn't care. You're going to have a date with Emma Swan. You would have talked more but Emma saw Regina leave so she kissed your cheek and hurried to Regina.

Snow
Awhile after catching her, you bumped into her at a ball. It was Prince Eric's ball, you knew him since childhood and wanted to attend. You saw Snow with a red hair girl and automatically thought they were together. A pang of jealousy hit your heart but you didn't know why. Snow robbed you, yes she was desperate and yes she almost gave back instantly. But still. She robbed you.

When you saw the red hair girl and Eric dancing, you were so happy for two reasons. 1) Eric looked so in love with this girl. 2) you now knew the girl wasn't with Snow. Knowing this you walked over to her.
"Ah hello little miss princess" she greeted you. You smiled and curtsied, causing Snow to give you a sweet giggle that made your heart flutter.
"Snow, what are you doing here??I thought a bandit needed to stay out of the spotlight" you asked with a smirk. Snow told you about the girl, the mermaid who loved your friend. You thought it was honourable that she was risking her life for a friends.

"Do you ever miss this? Balls?" You asked and she hesitated. You could tell you said something wrong and as you began to apologise she spoke.
"I miss my father and my mother. That's it" she responds and looks down.
"Well...you're always welcome to come to a ball with me" you offered and she looked at you. She was smiling, showing off her beautiful smile.
"Like date?" She asked. Was it a date? Do you want that? You didn't have to hesitate. You nodded and she smiled even wider.
"I'd love too"

Killian
He was going to set sail soon. He didn't want to leave and tried to delay the journey as much as possible but he knew if he stayed longer he would never leave you. Even though you two weren't dating yet it was obvious there was something going on.
The day before he was due to leave you went to see him on the ship. He ordered a barrel of rum and beer from the tavern you worked at so you had to see him anyway.
"Y/N, what are you doing here?" He asked walking over to you. Normally he would meet you at the tavern.
"I came to see if you still want the beer and rum you ordered" you explain and he smiled used his good hand to hold yours.
"Yes love. Also, since I leave soon I have a proposal to make" he announces to you. You raise your eyebrow. Not an actual proposal you hope.

"Before I leave ask that you allow me to take you for a walk. Like a date" he calmly speaks and you smile. Nodding your head, you did like Killian and you knew you would miss him when he left. Despite possibly never seeing him again, you wanted to make sure you spent as much time together as possible.

Henry
He really, really liked you. He always told himself he would ask you out in the most romantic way possible and as it turns out, you beat him to it. Although, when he asked you if you wanted to watch a John Hughes movie marathon you did think it was a date. So one day after science class he built up the courage to ask you out, that was until he saw you talking to Hansel and it really knocked his  confidence.

"Hey Henry can I talk to you for a sec?" You asked after you approached him at his locker. He looked sad and he was, he was jealous of Hansel; you two always talked and it annoyed him because he wanted to talk to you all the time. He wasn't your boyfriend but he wanted to be.
"Sure...what's up?" He asked without looking at you. You sighed and turn't him around by his shoulders.
"Do you want to go on a date with me this Friday night?" You asked, causing him to become gobsmacked. He was not expecting it, he thought it would be about to your science project, not ask him out. After at least a minute of him being in total shock you sighed and started to walk away, until you heard him say
"What time should I pick you up?"

Jefferson
After he found Lady, you two became close. You would meet every morning at the park as you walked Lady, then went to get lunch at Grannys. It was a nice add on to your routine and it made Jefferson less lonely. Every once in a while you would go to his house for some tea, it was huge. Your feelings for him grew as you saw how good he was with Lady (she was like a daughter to you) and you were sure he felt the same way. He would blush when you complimented him and always smiled when he saw you approach him.

But he was the one who asked you out. On a usual Monday morning you took Lady to the park and waited for Jefferson who was surprisingly late. Turns out he was buying you some flowers, when you saw him with a bouquet of y/f/f *your favourite flower* it made you smile brighter than ever.
"What's all this for?" You asked as you walked over to him. He smiled and handed you the bouquet.
"Well Miss y/l/n, will you do me the honour of going on a date with me?" He asked, clearly a little nervous but he was also very confident.
"Well of course, I'd be happy too" you replied.

David
It was during Rumplestiltskin's visit, when he found out about James. He walked over to your cottage and saw you picking berries. You turned your head and saw him.
"David? I didn't know you were coming to visit". He sighed and walked over to you, clearly stressed. His hands where shaking and that was a sign he was worried.
"What's wrong?" You asked and you held his hand to stop the shaking, something that always worked ever since his father died.

"I have to leave for sometime" he announces in a hushed voice, at first you thought you misheard him but once you looked in his eyes you knew he wasn't lying or joking.
"An opportunity has come up to save the farm and I have to take it" he tells you, what could it be? He would never leave his mother, or you. You nodded your head, trying to be supportive.
"Promise me something, when you get back. We'll go to a tavern and talk about everything, and I mean everything" you say and he smirks.
"Like a date?" He asks with a goofy voice, you roll your eyes playfully. You didn't mean to ask him on a date. It just happened.

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