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"One hot chocolate Ruby…Sheriff's orders…Ha! Get it-It's MY order…" Emma said with a laugh while Ruby just looked at her less then impressed with the early morning attempt at humor.

"You're awfully chipper this morning, what's up?"

"I have finally figured out the perfect plan to get Regina to go out with me."

"I thought we figured that out last week when you decided to "woo" her by sending her flowers and wine everyday from her secret admirer?"

"Well obviously it wasn't the perfect plan since all it got me was a giant credit card bill and the guy at the liquor store a date. You know that she actually thought he was the only person that would know enough about what she liked to send her her favorite wines? And that the sleeze actually took credit for it all?" Emma shook her head in disgust while Ruby just patted her hand as she set the Sheriff's hot chocolate down in front of her.

"At least the date went awful. I heard he ended up with a plate of spaghetti on his head after suggesting to her that maybe if things went well enough at the end of the night there might be a couple more free bottles of wine with her name on them at the store. I mean after that you shouldn't have to work too hard to look like a winner in her eyes right?"

"I don't know-she thinks she's sure of her feelings for me and they aren't good. But my new plan can't fail. I am just going to ask her out. Repeatedly. Until she says yes."

"That's your grand plan?"

"It's the only thing that I haven't tried yet. I figure I'll get a few no's, she'll start to wonder what I am really up to and eventually say yes just to find out. Then all I have to do is plan the perfect date, win her over, and Bam! Here comes Emma with the baby carriage…"

"First of all you already have a kid together and second of all I can't wait to see how this goes because here she comes now. Time to begin Phase 18 of Operation Tame the Dragon." Ruby said with a smirk as she grabbed the coffee pot and went to seat Regina in a booth.

"I told you to quit calling it that." Emma said in a hushed mumble.

As Emma finished off her hot chocolate she watched Regina out of the corner of her eye get settled into the booth and place her usual order with Ruby. The brunette was wearing one of those damn pencil skirts, a white button up shirt with one to many buttons undone to be classified as business attire, and red heels that made the Mayor's legs go on for miles. As she took off her jacket Emma couldn't help but turn her head just a little bit more to try and get a better look.

"Can I help you with something Sheriff?" Regina said startling Emma back to reality. Apparently she hadn't been as smooth as she thought.

With a quick glance at Ruby and a deep breath Emma pushed off the counter and wiped her palms down the front of her jeans. Sweaty palms were the worst but hopefully that was the only sign of nervousness that showed-it wouldn't do any good to suddenly lose the ability to speak. This had seemed like the perfect plan this morning when she had woken up to another dream about the woman she was now just standing in front like an idiot with a dazed look on her face and possibly with her mouth hanging open.

"Sherriff!"

"Crap, sorry spaced off there for a second. You're pretty. To look at. Can't seem to help it around you. Want to go on a date with me?"

"…"

"Please?"

"…" Regina just stared at her like she had lost her mind. Or forgot who she was talking to.

"Okay well I will just let you think that over. I'll talk to you later. I have to get to the station. Lots of sheriffing to do today. Bye." Emma said while inching backwards towards the doorway.

As Emma left the diner the sound of the bell chiming above the door broke Regina out of her stupor. Did the birthmother of her son really just ask her out? What in the world was that about? Surely it was just a cover for something else. What could Emma be up too?

"Refill on your coffee Madame Mayor?" Ruby asked as she watched the brunette's eyes track Emma down the sidewalk with a murderous glare.

"No thank you I actually need to get to the office. I forgot I had a conference call at 9:00." Regina said as she quickly gathered up her things and left the diner. Without even paying.

"This is definitely going on Emma's tab." Ruby mumbled to no one in particular. "I can't believe she actually did it."

SQSQSQSQSQSQSQSQ

When Regina arrived at her office she still couldn't figure out what Emma was playing at. Sure she had noticed that sometimes the blonde's eyes lingered on her lips a little too long and she sometimes caught her staring at her ass but surely that didn't really mean she wanted to date her. What was it with everyone in this town suddenly wanting her and feeling like they had the right to approach her, even indirectly? First it was the mailman-even though he denied being the one to put all the little love notes in the mailbox for her, then it was the jerk who owned the liquor store, and lately she felt like Ruby had been watching her and trying to go out of her way to be extra nice to her too. Now Emma was in the mix and she had no idea how to feel about that.

Two hours later when she had finally started digging into her pile of work her phone beeped telling her she had a new message. From Emma.

So about that date.

Regina couldn't believe it. She had actually decided that she'd misinterpreted the whole incident at the diner and wasn't going to give the situation another thought. At least til she got home and cracked open a bottle of wine. But the Sheriff was apparently not going to let that happen. What in the world was she going to say back? She didn't want to completely shut the blonde down yet, first she had to figure out what her end game was.

I don't know what you are referring to Sheriff.

There, make Emma spell it out again and maybe she could get some answers.

The diner this morning. I asked you out on a date. Said you were pretty?

Well that was straight to the point. And an accurate re-cap. Now what was she going to say? Oh yeah I forgot?

I assumed you had suffered some kind of head trauma when you spoke to me this morning and decided to not embarrass you further by mentioning it.

Ok, insult her and make it seem like she was trying to be at least polite all in the same text. This was definitely some kind of head game Emma was trying to play with her. Well no one beat the former Evil Queen in head games.

Decided NOT to embarrass me? Don't go soft on me now Madame Mayor-I like you just the way you are. That's why I asked you on a date. I guess you haven't made up your mind yet though so I will just give you a little more time to think about it.

Okay. So that did not go how she had expected. How dare Emma assume she hadn't decided yet, or even that she was contemplating going at all. If she were to decide to play along it would only be to see where this little scheme was going. She would gain the upper hand back by just not bothering to text back anything and make her wonder. She had her own way to get answers and she knew just how to do it.