"So how are you liking the hospital so far?" Emma inquired, peering over the rim of her glass at the younger woman seated across from her. She had decided it would be best to start off with a simple, neutral topic and then move onto more personal conversation as the night went on.

"I love it. It's everything my dad said it would be and so much more." The brunette smiled, taking a sip of her wine, her fingers twisting the stem of her glass slowly.

"He worked at Sapphire Lakes?" The blonde raised her eyebrows in surprise. She was familiar with the work that Regina's father and mother had done throughout their careers and had even found inspiration through some of their innovations.

"Yeah, for the later part of his career he did. He retired a few years ago once he decided he wanted to spend more time at home." She replied simply,taking another sip of the sweet wine. She would give Emma credit for the selection.

"What? That's awesome. I didn't even know. He must have left shortly before I started my residency." Emma hummed, watching the brunette with intrigue.

"Yeah a lot of people don't know that. He came here and left my mother and I back in Maine."

"Oh I'm sorry I didn't know your parents weren't together."

"No no no, they are. They just figured that separating for the sake of their jobs was the best thing to do."

"Wow. Are they still together, like to this day?"

"Yeah, they're going on 50 years soon."

"That's amazing. I wish I had that kind of connection with someone."

"What do you mean? Haven't you had relationships before?" Regina looked curious and leaned forward a bit, setting her glass on the table and resting her chin in her hand.

"Well yes and no. I'm very offset and I usually keep to myself despite the several friends I do have. I haven't always been great at relationships so I found it easier to….keep it casual." Emma explained, grimacing a bit at having to tell her date that she had "casual" relationships.

"What about ? You two seem to be as close as I can imagine. Surely you must've….thought about it, at least?" She implored, brown eyes watching the blonde squirm.

"Well, Ruby's like my sister. Her mother abandoned her and her father died in a freak accident so she was left with her granny, which is the woman who raised me." Emma smiled at the thought of the elderly woman. She was tough, but she was fiercely loyal and protective of her own.

"Wait, Granny? As in Eugenia Lucas?"

"Yes, why? Do you know her?" Green eyes sparkled with surprise that the younger woman would know someone from her life outside of Boston.

"Yeah, I love her. Her food is what made my senior year great. I love Granny's Diner. It was my absolute favorite place in all of Maine." Pearly white teeth appeared between red lips as she recounted a brief portion of her time in the seaside state.

"You went to Storybrooke High? Where Ruby was from? I thought you grew up in Boston."

"Yep I graduated a year early too. I did." Regina laughed, taking a sip of her wine again. "I was born in New York and we lived in Brooklyn until I was six. We moved to Boston, upper west side, because my father got a job at Sapphire Lakes as the Head of Cardiology. When I was sixteen, my mother got offered a position at Silver Pine Regional Hospital to head their Innovative Surgical Program." She paused for a moment, biting her lip as she thought over her high school years. "My parents didn't agree on what they wanted to do. My mother wanted to take the position, but my father wasn't ready to give up his position at the hospital nor did he want to relocate. He's never really liked Maine. So, they decided that the best thing, for their careers and their relationship, was to separate, temporarily, and focus on their work. I went to live with my mother in Maine because it made sense at the time."

"Wow, so you stayed in Maine until graduation and then what? Went straight to university?" The blonde encouraged the younger woman to keep going, finding herself enamored with learning about the history that made Regina Mills who she was.

"Yes, after graduation I packed up my room and I drove back to New York. I graduated third in my class at Albany Medical School. I stayed in New York until my last two years of school at Harvard Medical just like my father did."

"Wait, wait! You went to Harvard Med?" Green eyes widened in astonishment.

"Yeah. I wanted to finish out school the way my father did and I wanted to be closer to Sapphire Lakes for the internship program." She smiled shyly at the older woman, ducking her head and toying with her necklace.

"Really? Wow, I really need to sit down and read your profile."

"You haven't read it?"

"Not yet. I was too focused on trying to be a hard ass on you that I didn't even get the chance to read your thing." The blonde grinned at her, shrugging a bit.

"I feel like I should be offended by that." Regina feigned a gasp, pressing her hand to her chest in mock astonishment.

"I mean, I don't know, maybe you should be." Emma shrugged and chuckled as the brunette flicked a few droplets of water at her, wiping her fingers on her napkin.

The flirty banter was interrupted by the reappearance of their server carrying a tray laden with food. He smiled politely and laid out their assortment of sample dishes before them, grating fresh parmesan over certain pasta dishes with a flourish. "Mademoiselles, is there anything else I can get for you this evening?" He looked at each woman respectively as he broached the question.

Emma looked at her date for confirmation that everything was to her liking before shaking her head. "No, thank you. Everything looks wonderful."

The man gave a small bow before retreating back towards the kitchen.

The two women looked over the array of dishes, each labeled with a neat sign with the name of the dish printed on it in curling letters.

"This is all so amazing, Emma. How did you even get a reservation here?" The brunette looked across the table at her companion in awe.

"Let's just say I saved the owners life."

"No way"

"Well, I did. Triple bypass with a valve repair." She recounted proudly, carefully cutting into one of the pasta dishes and beginning to plate small portions onto each of their plates. "It was a hell of a struggle but Marco pulled through with flying colors,"

"You're such a legend."

"I am not. Your father is a legend. I'm just someone trying to make a name for herself."

"You're doing an amazing job, might I add." Regina remarked as they began to eat, both pausing to hum in appreciation of the delicate flavors woven into the dish.

"You think so?"

"Yeah, I wrote my college paper on you and all your achievements. Of course you're doing an amazing job." She insisted, blushing a little at the knowledge that she had just admitted to writing an entire paper about her date's life.

"I mean, I guess so. Thanks Regina".

The rest of the evening consisted of laughing, talking and drinking. The couple finishing the entire bottle of wine between their dinner and the accompanying dessert. By the end of the night Emma was a little too tipsy to drive and Regina didn't trust herself to drive Emma's Tesla all by herself, lest she dent it on a light post.

"I can call us a cab." Emma stated easily, pulling her phone out "I don't wanna drive since we've been drinking. I'll just have Ruby come pick up the car later." She added thoughtfully, dialing the number for the cab company.

"Oh, okay" Regina shifted uncomfortably, not really knowing how she was getting home other than Kathryn who would make fun of her the whole time for not fucking Emma. She grimaced at the thought and fished her phone from her clutch to check the time, wincing when she saw that it was past 10:30 already.

The blonde finished ordering them a ride back to the condo, glancing over to find Regina shifting her weight from one foot to the other to try and stay warm.

"Oh you must be so cold. I'm sorry." Emma took off her jacket and handed it to her,

"Oh no no it's okay I'm fine" The brunette blushed, trying to keep her teeth from chattering.

"You have the goosebumps, you're not fine" Emma stepped closer to Regina and slid her jacket around the smaller woman's shoulders, her hands running gently up and down her arms to try and warm her up.

The cab driver pulled the car up to the curb and smiled at the pair standing close together on the sidewalk. He watched as the blonde woman helped the petite brunette into the backseat before asking for an address. Without thinking Emma provided her address to the man as opposed to asking Regina for her own.

The drive to the blonde's apartment building only took a few minutes and soon she was helping Regina from the car, counting out a few bills and handing them through the window to the cab driver. She took the brunette by the hand and led her along an expansive hallway to a pristine elevator, leaning on the wall a bit as they ascended.

"My apartment is just down here." She motioned down the hallway and dug her keys from her pocket, slipping the correct key into the lock and pushing the door open. She made her way to the living room and sank onto the couch, closing her eyes with a groan.

Regina followed slowly, taking in the decor and furniture that decorated the older woman's home. The space was breathtaking with windows overlooking the main portion of the city.

"Um Emma?" She smiled shyly at the blonde. "I'm still here…."

"Oh shit. I completely forgot that you didn't park here. It's okay. I have a guest bedroom upstairs to the left of my own. It has a private bathroom and fresh sheets." She got up off the couch and took the brunette's hand in hers.

"Oh no, are you sure? I could always call Kat to come and get me." The young intern looked unsure about intruding on her date later into the night.

"No, it's no problem. it's late anyway. Besides, the bed in that room is crazy comfortable." The older woman offered with a smile, leading her towards the stairs.

Regina smiled and walked upstairs after the blonde "I don't have anything to change into." She chuckled in embarrassment, suddenly feeling shy. They had such a nice night together, in her opinion.

"It's okay I'm sure I have extra sweatpants or something. Gimme a second." The blonde held up a hand and disappeared from the room in search of the aforementioned clothing.

Regina giggled "Okay." she smiled and started to take off her dress once the door was closed. Under her dress she wore Nike pros and a lace bra, she set her dress on the dresser and her heels by the door. She walked over to Emma's room and knocked gently on the open door. "Any luck finding anything for me?" She inquired, blushing as green eyes roamed her body.

"Oh, um, yeah. I found some stuff that should work." Emma murmured, holding out a pair of red and black plaid pajama pants and a "Yale" t-shirt. "I can take you home in the morning or...the afternoon. Maybe we can get breakfast?"

A smile bloomed across Regina's face and she nodded. "I would love that. I can um...I can cook, if you want. I may really amazing apple pancakes."

"Apple pancakes sound amazing." The blonde nodded in agreement, moving closer to the brunette. She leaned down and pressed a soft kiss to her cheek. "Good night, Regina."

"Goodnight, Emma." She smiled and turned to make her way back to the guest room, peeking over her shoulder. "Thanks again, Doctor Swan, for an amazing night."