Author's Note: I do not own Once Upon A Time or its characters. Just a fan

"I want to be casual, you know, like relaxed and cool," Emma said to Henry as he packed his bag to go to his other mother's house.

"Have you ever actually done this before?"

"Yes," she said defensively. "Listen kid, a lesson you will learn pretty quickly – we girls grow up with the expectation that a boy asks us out. We don't want to be the one doing the asking."

"If this you teaching me how to ask a girl out, I think I will ask someone else for help in that department when it comes to it. Maybe Killian."

She shot him a dirty look.

"I am just saying that for a girl asking a guy out it's a really big deal. We are putting ourselves out there completely. And like me right now trying to figure out how to do this it is doubly hard because I am not going into it confident of what the answer will be so you know I have to play it like the answer doesn't matter."

"But the answer does matter?"

"Very much so."

"Now you are confusing me. Can we go?"

"Yeah kid, let's go."

They drove to Regina's house and Emma walked him to the door and knocked. Regina answered the door looking impeccably tailored as always.

"You are late Miss Swan. Again."

"Hey, blame it on the kid. He's slow."

"Goodbye," Henry said to Emma. "And thanks a lot for throwing me under the bus."

"No problem. See you on Sunday."

Henry moved past his mothers and went upstairs.

Emma continued to stand there.

"Was there something else?" Regina asked.

"Um yeah, I wanted to um ask you something."

"Ok, what is it?"

"Um, you know I was just um talking with Henry, and you know he is growing up quick and everything so he's going to be like dating and stuff soon and then driving a car and then graduation."

"Is there a question in there somewhere?" Regina asked raising her eyebrow.

"Um, no, I mean yes I have a question. I um … damn it … willyougooutwithme?" she blurted out.

"I'm sorry I am not sure I heard you right. Could you perhaps say it slower?"

"Will you go out with me?" she said slower. "You know, a date, just you and me, no kid. Just us. Dinner or something."

"Yes, Miss Swan that would be agreeable."

"Really?"

"Hopefully your conversation skills improve by the time you take me out."

"What? Oh, yeah," she smiled. "Well um I should go and when I pick up Henry on Sunday maybe we could finalize plans then."

"I will see you Sunday then. Good evening Miss Swan."

"Bye," Emma smiled as she took steps back but caught herself before falling off the stoop like an idiot.

Regina closed the door after she was sure Emma wouldn't hurt herself making it back to her car.

"How did she do?" Henry asked from the top of the stairs.

"About as bad as expected," Regina smiled. "But it was cute. Thanks for not tipping her off about what my answer would be."

"I almost did, but only because I thought she was going to break out in hives because of how nervous she was."

"Well I appreciate you encouraging her to finally do it."

"If you wanted her to ask you so bad, why didn't you just ask her instead?"

"Because she might have said no. You will learn Henry as you grow up there are certain nuances involved in asking a girl out. It's not as easy as it looks."

"If this is you trying to teach me a lesson on dating, I think when it comes to it, I will just ask Robin for advice."

Regina shot him a dirty look sending him back to his room.