Henry stared into his laptop screen intensely as he typed. Emma looked at him like he was crazy but didn't say anything. The boy looked like a madman though.

"Are you sure your eyes aren't burning or something?" Emma asked from the other bed in the room. He glared at her still typing and then turned back to his screen.

"I'm fine," he murmured.

Emma rolled her eyes and suddenly blurted out, "Do you think Ruby really wants to hang out?"

"Yeah, I really do."

"Smartass."

"You asked and I answered with my honest opinion. Ruby's nice and I think she really likes you."

"Really likes me?" Emma frowned.

"Not like that…well I don't know maybe. Somehow you charmed a lady on your first day," Henry snickered.

"Haha, funny." The boy ducked the pillow flying his way and quickly threw one back. He choked back a laugh at the look on his mother's face as the pillow hit her square in the forehead. There was a pause and Henry looked at her carefully watching her every move. She swiftly scrambled off her own bed and jumped onto his, ready to pounce on him.

The teenager grabbed a pillow and leaned away to protect himself. He put a hand out to stop her attack, which was no doubt going to consist of sever tickling, "Whoa, wait…you have somewhere to be. Ruby gets off in five minutes. You're going to be late."

Emma retracted her hand from his waist and sat back on her knees, checking her watch, "You're lucky. I'm going to get you eventually, kid."

Henry groaned in response, "Not the sneak attacks."

"Yes, the sneak attacks." She got and flew the laces of her boots and grabbed her jacket. Her hands hovered over her keys and she turned around to Henry already back to his writing, "Do I look okay? Should I change?"

"You look fine, Ma."

"Are you sure?"

"Positive." He looked up from his screen. "You know this is exactly why you need Ruby."

"What are you talking about?"

"You ask your fourteen-year-old son for advice and if this outfit or that one will impress that guy or this girl. I don't know. I haven't even had a girlfriend before."

"Oh…" Emma had never really given it much thought. "I'm sorry, Hen. I never realized I was putting that kind of thing on you. I really do need some friends. Nate was no help for the same reason."

"It's okay mom. I'm not upset about it. I just don't think I'm much help."

"You do okay for a secret wingman, kid." Emma smirked walking over to the bed as he crawled to the edge and sat up on his knees. She ruffled his hair and he pretended to hate it like always but still hugged her. Emma kissed his cheek and pulled away. "I'll be back in a couple hours. Don't stay up too late."

"Of course not," he said watching her pick up her keys and head for the door.

"And no wild parties. No drinking…"

"Ma, seriously?"

"And definitely no girls."

"I got it," he called after her.

Emma shook her head as she closed the door behind her and exited Bed and Breakfast and hurried carefully across the street and over to the diner. As she made it to the door, Ruby rushed out the door out of breath with someone yelling after her. The blonde stared at her a little wide eyed as she panted and started chuckling to herself.

"Are you okay?" Emma asked in concern.

"I'm great. If you heard the yelling that was Granny…don't cross her like ever," Ruby laughed walking over to the blonde and looping her arm into hers. She started to lean them down the street towards their destination. Emma didn't bother to question it.

"Um, I don't plan on it. Are you sure you fine?" she asked instead.

"Worried I'm drunk already?"

"No you just-"

"Couldn't get out of there fast enough. All the needy assholes of the town show up when I have to get off."

"Ah, I see."

"Yeah, couldn't move quick enough." Ruby laughed unconsciously holding Emma's arm closer. The blonde noticed and grinned slightly but ducked her head to hide her blushing cheeks. Ruby stopped laughing, her ears twitching at a particular sound and she felt Emma stiffen a bit in her grasp. The brunette woman relaxed her grip and thought to apologize until the bright neon flashed in their faces.

"Hey, there's our stop."

"Whoa. That's a hell of a spot," Emma said seeing the obvious partying going on inside. It was a little surprising for her to see on a Thursday night.

"Yep. Come on."

Emma let herself be dragged in and she pleasantly noticed the calm atmosphere despite the appearance of a rave from the outside. She didn't have much time to roam the room as Ruby pulled her over to the bar counter and planted her in a seat.

"Four shots Oliver. I had long shift," Ruby called to the man behind the counter. He winked at her and fixed them up with shots quickly. "Thanks Olly."

"Shots already?" Emma asked glancing at the four glasses in front of them.

"Hope you planned to be out all night."

"I'm sure it's possible," the blonde said picking up her shot.

"So, what's your story blondie?" Ruby asked before knocking back her shot.

Emma's smile faltered. Ruby caught wind of it but didn't correct anything or brush it off. She just waited.

There was something in the woman's eyes. Emma couldn't pick out what it was but it was just natural to feel like she could trust Ruby with all her secrets and the woman wouldn't tell a soul. She trusted her even though they just met and she'd never felt like that with anybody. The brunette noticed her contemplation and she knew the blonde was catching on to the innate ability to get people's trust but she also was naturally loyal to respect that trust as well.

"I, uh…" Emma shook her head and blinked, "I grew up in Chicago like I said before. I was…an orphan. Went from home to home my whole life, ran away when I was 17, got into some trouble, had Henry, and got my life together. It's a real rollercoaster."

"Believe it or not, other than having a kid, I know exactly how that is."

Emma cocked her head to the side seeing absolute truth in the brunette's words. She nearly smiled at having someone understand her.

"What?" Ruby chuckled.

"Huh?"

"You keep giving me this look. I've seen it a few times," Ruby said taking down her shot.

"Oh, sorry. It's just…Henry says I have this superpower. At first I didn't believe him but I know when people are lying. And you weren't lying."

"Nope, not at all. I've been an orphan my whole life too and I've never stayed stationary until Storybrooke."

"I was somehow almost starting to think I was the only one," Emma smiled taking her shot and picking up another one. Ruby shook her head agreeing it felt weird to relate exactly to someone even if she was leaving out major details of her life. "So what was it like being an orphan in England of all places?"

"No better than here in America. It was hard. It was even worse not having anyone for so long. You kind of lose hope until someone drops into your life and makes it all better without even trying."

"Oh, yeah. I know that feeling."

"So what about you now? What did you do in New York?" Ruby asked smoothly shifting the tone of their conversation. Her life was just as she had vaguely explained it. There was something more emotional than that, if it could get any deeper than someone saving an orphan. Emma caught onto the emotion behind Ruby's short story and completely understood not wanting to talk serious details about it.

She smiled and answered, "I was a bail bondsperson for a while and then enrolled in the police academy. Spent four years working for the NYPD. I was a detective."

"Hot shot," the brunette said sounding impressed. "That's a hell of a career. Why did you say was?"

"I can stay in one place for too long. It's just not me. I was worried about uprooting Henry but as soon as that kid caught wind that I wanted to move, he was all for it. I've been getting transfer offers in my email for days now. I'm not sure where I want to go."

"I feel like I'm missing something…" Ruby said chuckling. "Detective…?"

"Swan. Emma Swan."

"Oh," the brunette said incredulously, "I think I've heard of you…"

"Really?" Emma frowned. "I'm famous?"

"I don't know. Are you?"

"Not that I know of. It'd be cool if I was though." The blonde thought out loud. "Henry would love it."

"I'm sure he would." Ruby laughed. "So, it's just you and Henry?"

"Hm? Oh, yeah. Just me and the kid."

The brunette was about to respond when a loud crashing interrupted her. Holding her shot glass in her hand, she turned in her stool to get a look at the commotion going on. She bit her lip trying not to grin at a how Emma startled was by the sound. She had to be the most adorable person ever. She could only imagine how much better it was knowing she could be a badass detective and still be…cute. Regina would so not be happy with her thoughts.

"What is…happening?" Emma asked in surprise. Her face fell into total shock at the fight breaking out across from them.

The brunette gulped her shot, grinning in amusement, "That is drunk Leroy and some new guy he's fighting."

"New guy? Don't you guys get new people here all the time?"

"Yes and no," Ruby explained distractedly, watching the short man tackle the ginger man into a pool table. Emma watched as well feeling her urge to break it up become nonexistent. Usually when she was at a bar and a fight broke out, even though she was off duty, she still took it upon herself to stop it. This time, however, she was relieved at the thought that she didn't have to. She could look on in amusement.

"I just meant Leroy fights a new person every night. He's our town drunk. If you're ever looking for him, you'll find him more often than not…with that guy." Emma followed her finger to the tall man suddenly in between the two drunks. He was in a brown sheriff's coat and the badge on his hip shined brightly as it hit the light when he moved.

"The sheriff?" The blonde frowned looking over to Ruby who immediately met her eyes with an amused smile. Emma sighed internally, silently request the brunette stop smiling at her. It was not at all uncommon for this woman to be considered attractive.

"Yep. That angry little man spends most of his time in a jail cell at the station."

"That's…" Emma glanced over to the short man trying to overpower the sheriff and was painfully unsuccessful. Surely he should have known that. The taller man looked like a brick wall from a mile away. "Actually hilarious."

"Ruby heads up," Graham called across the room seeing as Leroy made a fast moving, drunken beeline for the two women at the counter.

The brunette turned away from Emma just in time to see him coming and leaned away as her collided with the counters edge, tipping Emma's drink onto herself. Ruby huffed, irritated, "Leroy, you idiot." Graham appeared shortly, cringing at the narrow look he received from Ruby, as he pulled Leroy away from the bar.

"Sorry, ladies," he said pulling the drunk man towards the Rabbit Hole's exit. "Next round's on me, 'kay."

"Whatever, Graham. I'm running up your tab," Ruby called after him. He smirked back at her as he left off with both men cooperating out of alcoholic exhaustion.

Emma watched the exchanged and gave Ruby a look, "Are you two…?"

"Oh, um…" the brunette didn't know how to respond. Emma would know if she was lying but she also wasn't going to publically put a label on her relationship with him. Regina would be pissed since even she wasn't aware of anything. "It's…complicated."

"Hm, do I get the details of this complicated relationship?"

Ruby looked at her with an amused grin, "Something tells me you don't get to pry for that kind of information often."

"Yeah pretty much." Emma grimaced at the liquor stain on her shirt. Ruby looked down and sighed.

"I'm sorry about that. My car isn't too far. I might have an extra shirt in the back."

"No it's fine. Really."

"Emma."

"I'm serious," the blonde said pulling her jacket off and then beginning to undo the buttons of her shirt. Ruby looked at her like she was crazy but didn't say anything. After the third button, Emma revealed the white t-shirt under it and watched the brunette deflate in relief. "Afraid, I'd quit my day job to be a stripper."

"You'd be pretty damn good at it, though."

Emma looked up at her not knowing what to say. She clenched her teeth wishing for her cheeks to stop burning. She wasn't even interested in the woman like that yet almost everything she said had her blushing. Popping the last button of her shirt, she ran her hand across her face not seeing that Ruby was snickering at her.

"Don't worry, Swan. I naturally charm everyone I meet."

"No…" Emma started to shake her head but Ruby stopped her.

"Relax, babe. We're strictly platonic. Not that I don't think you're attractive because you are the best looking blonde I've met…"

"Oh…is it getting hot in here?" Emma took her last shot with her brow scrunched up.

"Okay, I'll stop. I promise." Emma sighed in relief, shrugging out of her shirt and dropping it on top of her jacket. "Hungry?"

"Starving."

She pulled the blonde up and they left off for a table after Ruby said only a few words to the bartender and he nodded. Emma looked between them in confusion with her shirt and jacket in hand. They slid into a booth and Ruby looked her in the eyes flashing her a smile, "You have a question."

"Maybe," Emma said uncertainly.

"Shoot. I'm an open book…within reason, of course."

"What's your story?"

"Oh…" Ruby breathed out a heavy breath. "I, uh, was an orphan like I said. I was adult when I finally got 'adopted' I guess."

"Really?"

"Regina Mills…"

"The woman that came in for coffee?"

"So you noticed the mayor?" the brunette chuckled. "Yeah, her. She saved me in more ways than even she knows. I don't know where I'd be if it wasn't for her. It certainly wouldn't have been here. I've spent every moment of my life with her since we met and I can't imagine that ever changing."

"She means a lot to you."

"Yeah, she does but you'd never notice. Regina likes to act too snooty to have friends but she's got the protectiveness of a brown bear…or worse."

"She does seem a little standoffish from afar."

"She's teddy bear but don't mention that. I'm not supposed to tell anyone."

"Assuming I ever have a conversation with the woman," Emma shrugged.

"You will." The blonde blanched at her words. Ruby bit her lip and continued, "If we're friends, you'll probably be introduced to my little circle. And the town is not that big you guys could run into each other often."

"Good to know."

"Oh she doesn't bite," Ruby laughed. Emma's timid grin fell away. She was lying and that worried her. The brunette noticed and corrected herself, "Okay she doesn't bite often."

"Funny…" Emma said. "Very funny…"


"Ruby, it's two in the morning," Regina sighed opening the front door.

"But your house is closer than mine," the younger woman argued tiredly. She received a raised eyebrow in return. "Come on, you wouldn't leave a pretty girl out in the middle of the night to get kidnapped."

"I have and I can if I want to. Unfortunately, no ever wants to kidnap you." The older woman step aside and let Ruby sluggishly walk through the door. As she passed by Regina scrunched up her nose at the liquor smell on her but then she jerked the woman backwards, who stumbled into her but didn't resist. Regina leaned close to her and squinted her eyes suspiciously. "You've been with a woman."

"Yeah, Captain Obvious. I was out with Emma."

Regina rolled her eyes, "That woman from the diner?"

"Yes, can we go to bed now?" Ruby asked leaning into Regina with the intention of closing her eyes for a minute. The older brunette only pursed her lips and pushed her off and in the direction of the stairs.

"You're going to be a pain in the morning."

"You love me and you'll put up with it. Now come on," Ruby said dragging Regina up the stair right as the woman closed the door behind her. Regina sighed but followed anyway hoping to catch up on some sleep. Although she had a feeling Ruby would disrupt her plans. They walked up the stairs and made it down the hall in record time before Ruby started to lose her legs. Impatiently, Regina grabbed her around the waist and pushed her bedroom door open to get them both inside and deposit the sleepy woman onto the bed.

As soon as she felt the silk sheets under her, she fell backwards, sprawled out over the bed. Regina slipped out of her robe and felt into her spot on the bed, shoving Ruby out of her space. The younger woman cuddled up to her when she laid down against her pillow.

"Go change and brush your teeth." Regina grimaced turning over on her side.

"My tooth brush is in the guest bathroom." She felt the heavy sigh that fell from the woman's lips and smirked lightly.

"Just take your shoes off at least…"

"'Kay." There were a few shifts as she slipped out of her shoes and laid back down under the sheets and pressing her back against Regina's. "Thanks for letting me stay over."

"Yeah, yeah," Regina mumbled into her pillow.

"I'll make you breakfast tomorrow…promise…" Ruby murmured, falling asleep almost as soon as her head hit the pillow.

Regina adjusted herself and shook her head, "Goodnight pup."