Disclaimer: I do not own Once Upon a Time or any recognizable characters

AN: I don't know where this came from. I've been watching that Singlebrooke Dating Service video on youtube far too many times.

Chapter One

Regina knew something was up by the way Henry and Kathryn walked into her office. The mischievous and scheming grins and glances they threw one another alerted the Mayor that they had a plan involving her and she was sure wouldn't like it. She glared between the two, switching her glance between her son and friend to see which would cave first.

"Regina," Kathryn spoke in a soothing hear-me-out tone. "We have something we want to run by you."

"The both of you?" Regina asked skeptically.

"Yup." Henry grinned.

The smile on his face made the brunette falter just a bit. Perhaps she could be open-minded to whatever their plan was.

"We think it'd be good if you got out more," the blonde said. The tilt of Regina's head and her raised eyebrow made her continue. "On a more personal level."

"I have no idea what you're referring to," Regina said with a shake of her head and continued to type on her laptop.

"Like a date," Henry answered.

Regina whipped her head up. "Excuse me?"

"Maybe you'll find True Love," the boy offered with a shrug. "That's all anybody wants anyway."

The Mayor turned her head to question the blonde. "You set me up on a date?"

"No!" Kathryn rushed to clarify. "No, I know that you'd like to be the one to initiate that sort of thing, but we. . ."

She trailed off as if re-evaluating her plan.

"What is it?" Regina questioned in her authoritative tone.

Kathryn winced, clearly wanting to retreat to the safety of her home and forget all that she and Henry had planned.

"We signed you up for a dating website!" Henry exclaimed.

Regina's eyes darkened as she glared at her soon to be ex-friend. She spoke slowly and enunciated her words. "You did what?"

"It's not necessarily just for dating, Regina." Kathryn pulled out a chair in front of the desk and sat. "It can be for pen pals, friendships, and yes, dating can occur."

The Mayor leaned toward her son and spoke kindly but firmly. "Henry, will you wait outside for me please?"

Henry stole a glance at Kathryn before sitting down in the empty chair beside her. "It was my idea too."

Regina rolled her eyes and sighed. Apparently the two had learned to gang up on her.

"We've made you a profile. Don't worry, we didn't use any personal pictures and your name isn't explicitly stated."

"I came up with a cool username," Henry stated proud of himself.

"Singlebrooke Dating Service is a legitimate website. I checked it out," Kathryn continued and pulled out a pen and a scrap piece of paper from her purse before jotting down some information. "And your profile already has some hits."

This intrigued the Mayor as she accepted the paper with her username and password. "MadameRegal?" She looked up skeptically.

"Cool, huh?" Henry beamed.

Regina pursed her lips and placed the paper off to the side of her desk. "I will look over the profile and will decide whether or not I will be keeping the account."

Henry grinned and hopped out of the chair followed by Kathryn. He looked up to the older woman as they exited the office. "She's gonna keep it."

Emma sat at her desk, relaxing with her feet up and a bear claw in her hand. These were the perks of being the Sheriff of a small town. Getting paid to do nothing. Just as she was about to take a bite of her pastry, Ruby, her part-time deputy, stuck her head in with a massive grin.

"Sooo," Ruby said waltzing into the office and sitting down.

Emma paused her bear claw track. "What?"

"So I was bored last week," Ruby began, "and I may have had a little fun at your expense."

Emma removed her boots off the desk and dropped the pastry back in the box. "Did you do anything that might get me fired?"

"No, of course not. I said fun, not career suicide."

Emma leaned back again and picked up the bear claw. She took a big bite and spoke around the food. "What did you do?"

Ruby grinned wickedly. "I used your traits on a dating profile."

Emma coughed and choked on the pastry. Once her throat was cleared she sputtered. "You did what?!"

"Relax, I didn't use everything about you," the young brunette said casually. "Just everything except your name and gender."

"Wait, my gender?" Emma leaned forward dumbfounded.

"I said you were a guy," Ruby shrugged and picked up a donut for herself. "A lot of ladies have been wanting to chat with you all week."

The blonde gave her friend an incredulous look. "Why are you telling me this?"

Ruby wiggled her eyebrows. "Maybe you'd like to chat with the ladies too."

Emma rolled her eyes. "Apparently I'm a guy."

"A popular guy."

Ruby stood and walked over to Emma's side of the desk, clicking away on her laptop.

"Singlebrooke Dating Service?" Emma read the screen with a laugh. "Seriously?"

"Singles in Storybrooke." Ruby dismissed quickly. She logged into Emma's account and stood proud. "Voila."

"KnightInRustyArmour." Emma laughed. "You couldn't have come up with anything better, Rubes?"

Ruby winked and turned to go. "You'll thank me one day."

"I doubt it," Emma mumbled and roamed over the site.

She clicked on her profile and wasn't surprised that Ruby hadn't included a picture. She was surprised by the number of messages it received even with the lack of one. Ruby must have written one hell of a profile.

She skimmed through until she reached it, reading it with fascinated wide eyes.

Early 30 year old blonde with a sense of humor that has been said rivals a child's. Loves to travel and adventures, but takes a snack and a DVD over it any day. Quite intelligent past the surface and never afraid to form an opinion. I'm a kind person and although protective of myself, I'm becoming more open with the formations of friendships. I'd say I'm worth it when you get to know me. Looking for a person who is open-minded, intelligent and not afraid of a stubborn me.

Emma shook her head in laughter after reading her profile. Ruby was creative when she was bored, Emma would give her that. What the brunette had written described Emma accurately and she was pleased to note that she didn't sound half bad.

Curiosity got the better of the Sheriff, so she clicked on her inbox messages.

Read ur profile. Would LOVE 2 meet with u! ;)

Emma scrunched up her nose. That was jail bait if she ever heard of it. She deleted it immediately.

I wouldn't mind shining up your armor.

Emma laughed and clicked the next one.

It seems you have some issues opening up to people. That's really sweet and sensitive, and hopefully one day you could open up to me.

Nice, but sensitive? Emma? No way. Delete.

Emma groaned at the numerous messages and just skimmed through the rest. It's not like she'd actually be using the site at all. It was just to look.

So look, she did. Browsing through random files, Emma's attention was caught on a certain MadameRegal.

I'm in my late 30s, attractive and a brunette. I am a single mother of 1, and my son is an extremely important part of my life. Men fearing children need not reply. My career is in politics-

Emma paused. This sounded strangely familiar.

My career is in politics, with my position being of great authority. Many are ruled under my thumb, so it's easy to see why I can be perceived as intimidating. In truth, I'm just looking for the right person for companionship. I am not a shy person, but I am private. I value my son, above all else, with honesty and integrity following.

Emma furrowed her brow. It couldn't be.

Those brave enough to reply, please don't waste your time if none of the listed above are to your liking.

Yup. Emma leaned back in her chair with wide eyes. That's Regina's profile. So Regina was looking for some love. Well, that was an interesting development.

Emma reread through her profile twice more before deducing that it was, in fact, Regina. Emma couldn't stomach the fact that the Mayor was looking for a little love in her life. Love that was not coming from her.

Though Regina's profile said 'attractive', Emma resolved long ago that the brunette was drop dead gorgeous. Attractive was more than an understatement.

Emma leaned back in her chair, her fingers steepled under her chin in contemplation. Well, there was only one way to know for sure if it was Regina. The obvious answer was to message her. If it wasn't, no harm no foul. And if it was, then Emma would get the chance to talk to her without it resulting in an argument, though she did love those, but it'd be the one chance to get to know the brunette.

What to do, what to do.

Before she knew it Emma had clicked on the 'Message' button on Regina's page. The window popped up, daring Emma to send the brunette an email. Her fingers hovered over the keyboard and began to type.

If I accidentally stole your pen name I am sorry. Great minds must think alike!