A/N This is a simple one shot possibly two shot. Sorry for any Spelling/punctuation mistakes.
Regina, 32, has never had much luck when it come's to love, she has been on a number of dates with men, that never went passed the first date. She only ever had two meaningful relationships, in her life and they ended badly.
The only ray of light to come out of it all, was her Son Henry, who she loved so much, he is ten, has brown eyes and hair like his mother and is a happy little soul and they live in town in Maine, very little happens in this town and Regina often wondered if this was it for her, a mon-fri job as Mayor and weekends spent, doting over her son and taking him to his grandparents or out with her best friend Katheryn and her child.
However little did she know, things were about to change...
"Regina, what are you going to do this valentine's? because very year, for the past three years, you have stayed at home and got drunk"Katheryn said, as Regina returned to the kitchen after putting Henry to bed.
"I wouldn't put it like that" she smirked, while opening a wine bottle.
Katheryn shook her head.
"Did you hear about the valentines event?" she asked.
Regina rolled her eyes.
"I think the whole town is well aware, dear"
Katheryn chuckled, taking her glass of wine in her hand.
"Me and Frederick are going, not to take part obviously, but for the entertainment"
"Okay"
"Why don't you come with us?"
"And what ruin your valentines celebration?" Regina teased.
"Nah, we've been together long enough now"
They then walked into the lounge and sat on the sofa.
"So, will you come, you never know you may find the one"
Regina scoffed.
"I gave up, a long time ago on finding love, dear"
"Well come for the entertainment then"
"I have Henry..."
"I am sure my babysitter, can look after Henry aswel as my daughter"
Regina raised an eyebrow.
"She has been good with Henry in the past, I admit that"
"You're come then?"
"Okay, what time is it again?"
"Were get there for around 7.00"
Regina nodded and they both took a sip of their wine, before Katheryn asked
"So, how's work going?"
"Fine, Pretty boring really, we got a new sheriff starting next week, I am yet to meet her"
"Oh yeah, Mary Margaret's daughter" Katheryn said in amusement.
"Yes, I just hope she is nothing like her mother"
"That would be awkward"
"It already is and I haven't even meet the woman" she started fiddling with her hands.
"I actually saw her yesterday, carrying boxes into Mary Margaret's apartment" Katheryn said.
Regina quirked an eyebrow, curiously.
"Yes and?"
"She's blonde, quite pretty really" she took a sip of her wine.
"Oh, doesn't look like her mother then, (she smirked) I guess that's a good thing, at least I won;t be reminded of the woman, at work"
Katheryn chuckled.
Across Town
"I am so happy that your finally here, honey" the pixie haired woman said, unpacking the last of Emma's boxes in her room.
"Yeah, I have a good feeling about this" Emma said softly, placing clothes in her wardrobe.
"This can be a new start"
"Yeah, Boston just didn't feel like home anymore, I tried you know, to make it work, but there's only so much I could put up with, you know"
Mary Margaret nodded.
"Have you been around the Town yet sweetheart?" Her father asked, coming to stand at the door.
"Not really, I've been in the Diner, that's pretty cool"
"Well, There's a valentine's event being held at the town hall, do you think you would want to go?" her mother asked.
Emma paused for moment.
"Um, I don't know, me and romance don't exactly work, I gave up on that months ago"
"Well, just come to meet the towns people, you may make a friend or two" Her father smiled.
"Are You two going?" Emma asked curiously.
"Yes, we kind of helped organize it, so we kind of have to be their honey" Her mother said, putting a jacket on Emma's bed.
"I'll think about it"
"Okay, well me and your father are going to go make Dinner"
"Okay, see you in a bit"
The next day
Emma walked into the Diner at 4.02pm, in her usual attire of boots, jeans and red leather jacket.
"Hot chocolate please" she told a brunette waitress, who grinned at her.
"Are you Mary Margaret's daughter?"
"Yep"
"I'm Ruby, I've heard a lot about you" she tilted her head at the blonde, while making the drink.
"Oh"
"Don't worry it's all good" she handed the drink over.
"Thanks, Il just go sit over there"
Ruby smiled and nodded and Emma made her way to the window seat and looked out, watching school kids and parents go by and a couple of minutes later, she saw a brown-haired boy, with a blonde woman and another child running towards the Diner.
They rushed in, going straight to the counter.
"Hi Katheryn" Ruby greeted.
"Hi Ruby, can i have two large cookies and a coffee to go"
"Sure" Ruby walked off and Emma studied the two kids, who were play fighting, they must be around ten or eleven Emma thought.
"Henry don't incourage her, I'll be having words with your mother, if you carry on" she smirked.
"I'm not scared of my Mom, (he folded his arms) everyone thinks she's scary, but she's a big soft cuddly bear" he chuckled.
Katheryn burst out laughing and even Emma found herself chuckling at the boys words, she found him absolutely adorable.
"Do you want me to tell her, what you just called her?"
"Um" he said shyly, looking to the floor.
A moment later.
"Coffee and two cookies to go" Ruby said, handing the items over and Katheryn paid.
As they left, Emma heard Katheryn say
"Now kids, Don't tell Regina you have had cookies, its our secret, okay?"
and then Henry said
"I'm not that stupid"
Emma chuckled again.
An hour later
"Hey Emma, you not want to go home yet?" Ruby said, coming to collect the empty cup.
"Not really, I am just enjoying the alone time, I'm not used to having company"
"Oh, Well your soon find you have plenty of company in this town, everyone knows each other here"
Emma sighed.
"Right"
"You coming to Valentines night?" Ruby suddenly asked.
"I think so, my parents want me to come, though I am not looking for love, if that's what your thinking"
"Sure, You've just moved here, I get it, it should be fun though, there's food, music, drinks, speed dating" she chuckled.
"Speed dating! Really! How depressing" she moaned.
"Don't be silly, it's going to be a laugh"
Emma chuckled.
"I'm gonna go, Il see you later"
"Okay bye Emma"
"Bye" and she walked out smiling to herself.
Valentines day 6.02pm
Emma was already at the Town Hall, as her parents were helping get everything ready for the speed dating. The hall looked pretty, with all the heart balloons and valentines banners, it looked more like a prom event, Emma thought to herself.
"Do you think eight tables is enough?" Mary Margaret asked, placing one of the small single table's down, with a seat either side, in the middle of the Hall.
"It may be too many" Ruby joked.
"Don't say that" Mary Margaret moaned.
Emma then tugged at her red dress, she had wanted to wear her jeans and leather jacket, but was persuaded, to dress up a little.
"Em's, come help me with these forms" Ruby said and Emma shuffled towards her and stopped at the edge of a table that had snacks on it.
"Right, these are given to the speed daters and they write, who they'd be interested in seeing again and If any match I let the women know first and they have the choice to go out on a second date or something"
Emma rolled her eyes.
"Really, this is like being a school or something" she muttered.
"Come on, it's gonna be fun"
Meanwhile across town, Regina had just put on her grey dress and done her hair and make up and was looking into her mirror
"This is just a social event, I am not looking for anything and will just go for a while and then come home" she told herself, before grabbing Henry and going over to Katheryn's.
Fifteen minutes later.
"Wow" Katheryn said upon opening the door.
"Hello dear" she smirked, at her best friend.
"Doesn't your mom look beautiful" She told Henry, who shrugged.
"I thought you said, you wasn't going to speed date?" she then asked Regina.
"I'm not, I just thought Id look nice, that's all"
"Right" Katheryn smirked and the brunette rolled her eyes.
Meanwhile back at the Town Hall, Emma was leaning against the wall, watching people arrive.
"Look Em's" Ruby said excitedly, coming to stand next to her.
Emma eyed her, cautiously.
"I will give you, free hot chocolates for a week, if you get all the spaces filled"she said eagerly, showing Emma the sign up form.
"No thanks"Emma replied firmly.
"Come on" Ruby moaned.
Emma shook her head.
"A month then?"
Emma pondered on it for a moment and then grinned.
"Deal"
Ruby grinned.
"Right, I need you to just get names and write them on there" she pointed on the paper, on a clipboard.
6.44pm
Emma was walking around with clipboard in hand, she had already managed to get eight names and needed another eight, five of which needed to be women.
"Hello, I'm Emma and i was wandering, if I could get you to sign up for the speed dating event?" she asked another small gathering of people.
"I will" one woman said.
"Great, Can you write you name here" she pointed to the paper.
7.02pm
Katheryn, Frederick and Regina walked through the door of the Town Hall.
"Its busy" Frederick said, as he began, to push through some people, to get to a table, with the drinks on.
"Why did I agree to come again?" Regina sassed.
Meanwhile Emma was wondering around on the other side, of the Hall and just signed up her 13th victim.
7.13pm
Regina punched a heart balloon out of her face, as she walked towards the bathroom, where she fixed her hair and thought, how valentines day is so depressing and she sighed to herself, before making her way back to her friends, who were kissing passionately.
"Ugh" she said, picking up her glass and guzzling it down.
They broke apart and chuckled.
Suddenly a blonde woman appeared in front of them, looking anxiously at Katheryn, who she had recognized, from the Diner the other day.
"Hello, I'm Emma and I was wondering, if any of you would be interested in signing up for the speed dating event"
"Well, me and Frederick are together, but Regina here, might do it" she smiled, looking to her friend.
Emma then glanced to Regina and her eyes widened, her breath hitched and her heart-felt, as if it had awoken, from its slumber.
And it was the same for Regina.
"I...no, I can't" Regina muttered, still holding the blondes gaze.
"Oh, That's okay" the blonde muttered softly, suddenly looking down at the paper, she could feel a fluttering in her chest, but tried to push it away, as she needed to concentrate on getting two more women to sign up and only had minutes to do it"
"Um, this may sound silly, but I need two more people to sign up and If i fail, I shall not receive free drinks for a month from Ruby, I would, Um, be willing to give you some of the free drinks, if you signed up"
Katheryn and Frederick chuckled, while Regina's mouth parted and she curiously studied the blonde from head to toe, admiring the dress, with particular interest at certain parts.
"You can't refuse an offer like that Regina" Frederick said.
"I...Fine" she replied, surprising herself by her answer, whilst still checking the woman out.
"Really?" The blonde smiled goofily and Regina now found herself entranced, by that smile.
"Yes" she muttered.
Emma stepped slightly forward, handing over the pen.
"Write your name on here" she said, as she took in, those dark chocolate eyes and the fluttering was back stronger than before.
Regina nodded and gulped.
A moment later.
"Thanks, I um, better get this one other signature then" she took a deep breath and moved away hesitantly but glanced back a moment later, to find the brunette staring after her.
A few minutes later, Emma was unable to get her last signature, the only option left, was herself.
"So, have I won" Ruby declared, happily coming to stand next to the blonde.
Emma sighed, before doing something, she never intended to do.
"Actually I won, I am going to take part" she said.
"Wow, the lengths your go to, for free drinks" Ruby chuckled.
7.57pm
Mary Margaret spoke into the microphone and the front of the Hall.
"Hello everyone, Can everyone involved in the speed dating, please come take a seat at a table, one Woman and one Man to each table, your find a piece of paper for each of you, for you to write who you would like to see again, rounds will last seven minutes and I shall ring a bell at the end of each, seven minutes and the gentlemen shall then move to the next table"
Everyone then took a seat and Regina didn't notice Emma, taking a seat at the table, next to her.
The Bell then sounded.
"Hello Regina" Sidney smirked.
"Hello Sidney" she rolled her eyes.
"I never thought Id see you, take part in this" he smirked.
"Well, someone was very persuasive" she smiled, not realizing Emma had heard her and she also smiled.
"So Emma, what do you do for work?" a dark-haired man asked.
"Oh, I am going to be the new sheriff"
Regina span her head round so fast, she nearly gave herself whiplash.
This woman is full of surprises, she thought to herself.
Two minutes later the bell sounded.
"Hello, I'm Will and you are?" a dark-haired man asked Regina.
"Regina" She smiled.
"Well Regina, may I say your very beautiful and I am surprised you are single"
"Your quite the charmer" Regina replied with a smirk.
"I can be (he smiled) and what is it, that you do Regina?" he leaned on the table.
"I am the Mayor"
Emma's eyes widened, as she found herself paying little attention to Sidney and was listening in, on Regina's conversation.
"Oh a business woman, I like that" he smirked and Emma tilted her head at him, with a slight glare.
"So Emma, your Mary Margaret's daughter?" Sidney asked.
"Yes, I am" she said, glancing back to Sidney and now Regina's eyes widened once more.
Of course, I forgot that detail, Regina thought, with a snarl.
Two minutes later the bell sounded again.
"Hello Love"
Regina leaned back in her chair.
"Killian" she groaned and Emma glanced curiously at the brunette, it was obviously Regina didn't like this man.
"My, My, looking for love are we" he teased.
"I gave up on that, a long time ago" she snapped and Emma found herself knowing, what the brunette meant.
"All you need is a good time, that will sort you out"
"Excuse me" she snapped.
"You heard"
"I will not lower myself to your standards" she snapped.
"Fine" he glanced sideways to Emma, who was now looking at Will.
"My, She's a Fine one, I shall have my way with her" he muttered but Regina heard.
Her Eyes blazed with fire, she clenched her fists.
"YOU WILL NOT" she snapped, causing others to look over at her.
Killian smirked.
"Oh, protective of this one are you"
Her eyes darted over to Emma, who was staring at her curiously but also longingly.
"No woman should have to put up with, your fowl mouth" she spat.
A moment later the bell sounded and Regina was pleased and concerned, because the next table he was going to was Emma's.
"Hello Regina" Robin said coming to sit opposite her.
"Can this get any worse" she said, looking to the ceiling and then brushing a hand through her hair.
"Hello Love" Killian said to Emma, giving his best grin.
"Hello" she replied, cautiously.
"Robin" Regina huffed.
"How are you Regina" he asked.
"Fine, and you?" she said, keeping an eye on Killian.
"So, when are you going to let me, take you on a date, you've avoided me for weeks" Robin asked.
"Robin, let me make this clear, I will not be going on a date with you"
"Technically were already on one" he chuckled and Regina groaned.
Emma felt bad for the woman's state next to her, it was her fault, for getting the woman into this.
"Emma, you are a pretty lass, would you like to get out of here and come to my boat"
"WHAT! are you mad" she said and Regina had heard and smirked.
"Maybe after a couple of drinks then?" he leaned over the table, giving his best grin and Emma leaned back.
Regina found herself leaning over and getting in his face.
"There is no way in hell, I am letting you get her drunk, so you can..."
"Who asked you" he interrupted.
"I...I am the Mayor of this town, so what I say goes"
He throwed his hand up.
"Please can you calm down" Mary Margaret interrupted and others were now watching the situation.
"Calm down! This is your daughter and this sleaze ball is being inappropriate"
"Killian is no harm to anyone, Regina"
Regina was dumbfounded, she shook her head and leaned back in her chair.
"Fine" she crossed her arms.
Killian grinned and turned his attention back to Emma, who didn't know what to think and as Killian chattered on, she found herself sneaking glances sideways at the brunette, who was still annoyed and staring passed Robin, who was chattering on about taking the Mayor out to a restaurant.
The bell suddenly sounded and as the guys moved, Emma heard Regina sighed and say
"Thankgod for that" she snapped to herself.
Emma smirked.
Once all the dates were done, nearly everyone started to walk away, with their papers to give to Ruby, but when Emma stood she noticed Regina staring down at a blank paper.
Emma's heart pounded, as she took a deep breath and went to sit opposite Regina.
Regina glanced up.
"Hello, I'm Emma" She smiled goofily and again Regina was putty in her hands.
Emma sat and glanced to the paper under Regina's hands.
"Did you not like anyone?" Emma said, pointing to the paper, whilst hers was folded in her hands.
"No, as you can see" Regina said, showing the paper to Emma.
"Well i hope free drinks will cheer you up" Emma smiled.
"Oh, you won the bet then" Regina smiled weakly.
"Yep and I want you to have all of them, for going through all this" she hoped this would make the brunette happy.
Regina was suddenly surprised, why was this woman, that she just meet, being so kind to her.
"That is very kind of you dear, but I can't do that"
"Why not, you deserve it"
Regina's breath hitched.
The blonde smirked, whilst leaning on the table, longingly staring into brown orbs and finding a swirling of emotion in them.
Regina clutched at the paper, she felt like a teenager with a crush, which was not like her.
They stared at each other for a few more, brief moments before Emma asked
"Maybe, you could join me for coffee tomorrow at the Diner"
"I can't...I shall be taking my son, Henry, to see his grandparents tomorrow morning" Regina replied softly.
"Oh Henry, I should have known, his the adorable kid I saw the other day" Emma muttered, with a soft smile.
"You know Henry?" Regina asked, with a hint of surprise in her voice.
"Yeah, I saw him with your friend at the Diner the other day, I assume that is the same Henry?" Emma stared at her.
Regina chuckled.
"Yes, That is my son" she smiled.
Emma relaxed.
"Well, would you and Henry like to meet me at the Diner, when you come back tomorrow" Emma asked, surprising herself with how eager she was to see the brunette again.
Regina's mouth parted and she thought
She doesn't mind that I have a son, am I reading to much into this!
"Yes, I shall be back around 4" she surprised herself again, with her answer.
"Cool, How about we meet at the Diner at 4.30 and have a coffee or something, it will give me a chance to get to know, my new boss better" she winked and Regina thought, she was going to explode with feels, but Katheryn interrupted.
"Hey, listen me and Frederick are going to go now, you want a lift back?" she looked between both women.
"Sure" she stood up and noticed Emma stand up.
"I look forward to tomorrow" Emma said softly and Regina went all doe eyed and Emma eyes went soft, as she reached for Regina's arm and lightly squeezed it, causing both to jump back slightly as blast of warmth was felt, upon the touch.
"Um, I better go hand this to Ruby" Emma said softly and gave a smile, before walking towards Ruby,
Regina rubbed her hand over, where Emma had touched.
What the hell was that, she thought.
"What was that all about?" Katheryn asked
Regina quickly shrugged and said
"I need to give this to Ruby, il be right back" and as she went over, Ruby was explaining to Emma, that all forms were only to be seen by her. So Emma bit her lip and quickly wrote a name down.
Meanwhile Regina had heard what she said and paused, deciding to write something on her paper before looking to Emma, who was scribbling down on her paper and she felt a slight sadness, that Emma must be writing down one of the guys names. She sighed and handed her paper over and said
"Goodnight" to Ruby, which Emma at heard and the blonde spun round and Regina caught her shining eyes.
"Goodnight Em-ma" she said so softly and meaningfully.
"Ni-ght Re-gina" The blonde replied, feeling somewhat awe stuck, as the brunette walked off.
"Oh making friends with the boss already" Ruby smiled.
"Yeah" she muttered, watching the brunette leave, as she handed over her paper.
"Are you going to come to the Diner tomorrow, for your free drink" Ruby chuckled.
"Um, I...yes, Regina and Henry shall we joining me"
Ruby raised an eyebrow.
Emma just chuckled and went to find her parents leaving Ruby to stare after her in surprise.
3 hours later and with everything cleared up, Ruby sat at one of the tables and started looking over the forms.
"Ugh" she muttered noticing Killian's comments.
All reasonable apart from a certain Mayor, who needs to get laid! However I require Emma for a further date and so on.
She shook her head and went to the next one and then the next, each one had said Emma.
Then she came to Emma's, which said, I will kill you if you mention this to anyone! but I didn't like any of the guys, but I did like Regina!
Ruby's jaw dropped, in complete surprise.
"Damn" she said, before re-reading it and then putting it to one side and going to the next
None! although I rather enjoyed, talking with Emma afterwards.
This time she burst out laughing
"Yeah right" she muttered to herself, before looking to the name and saw that it said, Regina.
"OH MY FUCKING GOD" she shouted, causing Granny to appear and ask what was wrong.
"Nothing, nothing at all" she replied, completely dumbfounded.