AN: So, I'm still the worst and apparently can only update once a month. Sorry, again. I promise I'm writing when I can but between a full time job and writer's block, I'm not doing so great at it. But here is another chapter, enjoy.

"Bloody hell Swan, this is a bar, not the library," Killian complained as he walked up to her. He had watched Emma walk in but he had been with a customer and it was too late when he turned back around. She had a textbook in front of her, her glasses perched on her nose and her hair pulled back.

"Jones, it's a Monday night and I have been in the library since I got out of class at 2," she explained and he glanced down at his watch to see it was nearly 8 pm.

"I think you need a break then."

"Why the hell do you think I'm here?"

"No, a real break." He reached over and closed her book, snatching it up before she could react. He placed it on the dry shelf behind the bar where he kept his personal effects. He moved to pour her a glass of rum, the higher end brand that she loved after a long day. He set it in front of her with a smirk and a glance over his shoulder to make sure he didn't have any customers waiting.

"Killian, give me the book back," Emma huffed and crossed her arms over her chest.

"You're going to drive yourself mad if you don't take a break from reading that damned LSAT prep book. There have been studies about this sort of thing, you know."

"I doubt those studies encouraged the use of alcohol during these breaks." He smiled at her and pushed the glass closer to her, Emma's eyes locked on the amber liquid the whole time.

"Just one sip to ease the tension." Her eyes moved to lock with his and her tongue moved to wet her lips. "Unless you'd like to ease that tension in some other way."

"You're at work." He gave a shrugged and winked at her.

"Trust me love, that's nothing that could stop me. Billy's over there clearing tables; he could cover for me and there is quite the supply closet in the back." She flushed at his statement and picked up the glass of rum to take a small sip from it. He poured himself a glass of the same rum to join her for a drink, infinity happy that Leroy didn't care if he drank behind the bar as long as there were less than 15 people inside the building.

"Don't you have other customers to bug?"

"Lucky for you love, everyone in here tonight is a regular and knows to just give a shout if they need my assistance. You can have all my attention tonight." She left out a small laugh and reached for a notebook from her bag. "Swan, I thought we just talked about you taking a break."

"I am. We need to make some ground rules for us and you know how I like to write things down." She opened up to the back for an empty page, clicking her pen a couple times.

"Don't you think rules are a little overkill love?" Killian asked to stop her from writing anything.

"I just...I don't want to mess this up." He reached over to take her hands in his, giving her a reassuring smile when she looked up at him.

"I know it's not going to be easy, us already living together. But it also makes certain things a lot easier." He linked his fingers between hers and gave her hands a squeeze. "I know we can do this. I'm not saying it'll be all butterflies and rainbows but we can make it work."

"I just don't want to lose my best friend because I'm shit at relationships."

"Emma Swan, you have yet to be in a relationship with yours truly. I'll help guide you. Besides, Ursula thought we make quite the couple already and that's just been us faking it." She laughed a little at that as he waltzed away to help a customer; the professor's words from this morning still fresh in Emma's mind. She had gone on and on how her and Killian had been the best at working through issues of all the couples. It wasn't a complete lie. This past month had been one of their most honest streaks with each other.

"Can you make me a promise?" Emma asked as Killian leaned back over the counter, grabbing her empty glass. He gave a nod as he poured out another round for the both of them. "If it does all go south and we end up breaking up, can we still be friends? I know it'll take some time but I've heard people make it work. I just can't go into this if I know there's a possibility I could lose you for good."

"Darling, have you learned nothing over the last four years?" he questioned as he set a glass back down in front of her. "I'm rather hard to shake. I'm afraid you're stuck with me for good." She gave a small nod and took a long drag from her glass. Killian moved around the bar as she placed it back carefully and turned to face him. He rested his hands on her hips as he stopped right in front of her, leaning in close to rest his forehead to hers. "Emma, I love you and I'm not even sure how long I have been in love with you. But this thing between us is the most real thing I have ever felt in my entire life. There is no reason for you to second guess this. So please know that I would promise you anything and everything because you already have my heart. I will do anything for you to make you happy." He moved to seal his promise with a kiss, knowing that he might have scared her but she needed to know. She needed to know that he was there for her through everything and she could set whatever standards to feel comfortable and he would be completely on board. She held every card in the deck for all he was concerned.

"If you really want to make me happy," she whispered as he moved to press their foreheads together again, "you'll go get ice cream with me once your shift has ended."

"If that's what the lady wishes." She rolled her eyes but gave him a quick peck on the lips before shoving his shoulders away. He gave her a cheeky smile as he walked back around the bar, picking up his own drink again. "What are you doing tomorrow night?"

"Probably just some more studying after work. Why?"

"I was thinking we could have our date." Emma swallowed hard at that, completely forgetting they were tasked to do that. She hadn't been nervous before. Well, perhaps a little. But now this would be their first real date. Just the two of them.

"I guess we should go out and do that."

"You make it sound like such a burden; being treated like a princess by a devilishly handsome Brit." She blushed at that, picking at her nail polish.

"You should know better, I'm no princess Jones."

"Aye, you're not but when you're out with me it'll certain feel like it."

"Shouldn't we do something a little more pirate-y given your fascination with them? We could just pillage and plunder instead." Her eyes flicked up to watch his eyebrow cock in surprise. She couldn't help the smirk that crossed her lips.

"It would be wrong to do such a thing on a first date, wouldn't you say?"

"Even though we've already slept together?"

"Mmm," he made the sound deep in his throat, causing a shiver to run up Emma's spine. "And I will treasure each and every moment of both times. But no, I won't be sleeping with you tomorrow unless that's what you really want. My only goal for the night is to take you out on a date to show you that this relationship is intentional and not just the two of us hanging out. You are right in the sense that we do need boundaries between roommates and being a couple. Going on dates is one of those boundaries."

"Since when are you the dating type?" she scoffed, trying to hide the fact that every word that just passed his lips was making her heart skip a beat.

"Since I started seeing this beautiful blonde girl. She's about your height, stubborn as the day is long." She glared up at him but he just gave her a wink. "Come on love, what do you say?"

"Okay." His face broke out in the best grin she had ever seen on him.

"Perfect. I'll pick you up at 7."

"Don't be late. I know it can be quite the trip over to my room."

"Aye but it's a trip I'm willing to trek."

…...

Killian's door was closed by the time Emma had gotten home from work. She could hear him playing his acoustic guitar softly and decided it was best not to disturb him. She had an hour and a half to get ready, she figured she'd use it all. But now she stood in front of her closet, questioning what exactly to wear for their date. He hadn't given any clues to where they were going or what they'd be doing. Emma sighed as she thumbed through her choices again, wishing this was all just easier. She would call Mary Margaret or Ruby in this scenario but she wasn't ready for everyone to know. There was no way a secret like that was being kept with Mary Margaret.

Emma reached into the depths of her closet, soft chiffon caressing her fingertips. She plucked it out to reveal the light pink dress she had worn a total of once. She had picked it out for her aunt and uncle's 25-year vow renewal last year. She shrugged and reached for the shoes she had bought with it as well. She quickly changed, glad she had decided to shave her legs earlier. If she wore a thick enough coat, she could hopefully not get too cold. She decided to chance it and pulled on the dress. She had already done her makeup, highlighting her eyes considering how much Killian loved them. She moved quickly to pull her hair into a styled ponytail, curling the ends just a touch. There was a knock at their apartment door and Emma moved quickly to pull her gray pea coat out of her closet.

"Killian, can you get that?" she called out at the second knock. "I'll be ready in just a minute."

"A little hard to get the door when I'm the one behind it love," she heard his muffled voice call back. She finished fastening her shoes before hurrying to open the door. Killian stood there, dressed head to toe in black. Black waxed jeans, black waistcoat, black button up, and his black leather jacket to top it off. He left his shirt open enough to show off plenty of chest hair and the edges of his new tattoo. She paused with the door fully ajar, her mouth gaping open.

"You look stunning Swan," he remarked. His eyes were bright as he took in her appearance, his face instantly breaking into a smile.

"You...look…"

"I know." She rolled her eyes and he pulled his arm out from behind his back, revealing the single rose he had. She smiled and took it from him carefully as he stepped forward. "Ready to go?"

"Let me just grab my jacket and purse. Can you fill a vase for me?"

"Do we even have a vase?"

"There should be a small one under the sink." She moved into her room and pulled on her jacket. Killian stepped in with the vase which she took to place on her nightstand. Emma dropped the flower in the fresh water and grabbed her purse before turning back to Killian. "Okay, I'm ready to go if you are."

"I was born ready darling." She looped her arm through his offered one, leading the way out of the apartment. "Do you want me to get a cab?" he asked as they rode the elevator down.

"How far is the walk?"

"Only a few blocks but I'd hate to cause you any pain." She laughed and shook her head as they stepped out of the building hand in hand.

"I'll be fine. These heels are surprisingly comfortable."

"I just didn't want a repeat of Halloween for you."

"And I appreciate it but I promise I can make it." They walked with their hands clasped together, Killian taking a route that was far from any of their usual restaurants. Emma tucked herself into his side as they made their way through the city. She couldn't give a single care at that moment even if one of their friends saw them. She was finally happy, after far too long.

…...

"Thank you for tonight," Emma said as she snuggled into Killian in the back of the cab. They had simply had dinner but it certainly was the best first date she had been on. It helped that they could skip all the small talk that usually occurred when dating someone new.

"I plan on taking you out quite often love so get used to it," he told her and pressed a kiss into her hair.

"Is that your way of asking me on a second date?"

"Perhaps." It was a short ride to their apartment but the air had chilled far more than Emma would have liked and Killian insisted on taking a taxi back. He paid the fare while Emma all but bolted into the building. Killian just smiled at her once he joined inside and take her hand to step into the elevator.

"Anything else planned for the evening?" Emma asked as the elevator dinged for their floor.

"Of course not, I am a gentleman. I'm simply making sure my beautiful date gets home pretty safe." He stopped outside of their door, taking her hands in his.

"You sure you don't want to join me for a night cap?" she joked.

"I wouldn't want to disturb your roommate Swan. Perhaps next time when one of us doesn't have an early class the next day." She rolled her eyes at him but she still felt her cheeks blush. His face transformed from his smile to something slightly more serious and hopeful. "That being said, will you go out with me again?"

"Take a guess Jones." Before he could say anything, she leaned in to press her lips to his. He gripped her around the waist and pulled her close, his other hand moved to cradle her chin. Emma wrapped her arms around his neck to hold him close. His lips glided over hers with ease and she sighed further into him. Killian wrapped his arm tighter around her as Emma stepped into him, both craving the other's body heat. Killian felt a stirring in his stomach to take it further so he pulled away, Emma lips trying to chase after his.

"I believe this is where I say goodnight love," he whispered and left one last peck on her lips.

"Positive you don't want to come inside?"

"Absolutely. Have a good night." Emma cocked an eyebrow as she unlocked the door but he made no move to follow, even going as far as to close the door behind her. She let out a deep sigh as she stepped fully into the apartment, wondering how dating her roommate felt so easy. She slipped off her heels and jacket before she heard the front door creak open, Killian entering with a smirk on his face.

"You look happy," she observed as if surprised that he could have that grin on his face.

"I'll have you know I went on quite the date tonight Swan," he explained as he shucked off his jacket to hang by the door.

"Is that so?" He gave an enthusiastic nod as an answer. "I thought you weren't the dating type."

"It's amazing what the right person can do to change your mind about that sort of thing." She felt herself blush at that, biting at her smile. "You look quite happy yourself."

"Maybe I am." She shrugged and made her way down the hall slowly. "Well, you know how this usually goes when I get home from a date so I'm gonna go change." He laughed as she stepped into her room and closed her door. She quickly pulled off her dress and changed into sweats and a tank top. She removed her makeup and rearranged her hair into a messy bun. Emma knew that she would have hated for any date to see her like this in the past but again, it was Killian. He had seen her dressed like this at least a half dozen times after dates before. It was just so different.

She shook her head at the thoughts and made her way back into the kitchen. Killian was standing there, also changed into sweats and a fresh tee shirt. His hair was ruffled, obviously having run his hand through it a couple times. He turned to face her with a smile and two mugs full of hot chocolate. He handed her the one that clearly had cinnamon dusted over the top.

"Princess Bride?" he asked as she took a sip from the mug he handed her.

"You know what, no." He gave her a questioning look over his own mug. "I usually watch my favorite movie after terrible dates to make me feel better. But I don't exactly have a need to feel better tonight." He moved to wrap an arm around her waist and pulled her in for another kiss. She tasted the rum on his tongue that he must have added to his own mug and she couldn't help the laugh that bubbled out of her.

"I'd say it's bad form to laugh mid-kiss Swan. It has a tendency to hurt a man's pride." She dragged her tongue over her bottom lip to gather a taste of the rum again.

"I'm sorry, it's just so pirate of you to taste like that, I couldn't hold it in. Besides, you know they say be with someone you can laugh with." She pulled him in close and rested her forehead against his. "I'll make it up to you, I promise."

"Aye, you can, later this week." He pulled away quickly to grab his mug again and took hers with it to the living room. "Let's see what's on Netflix then, shall we?"

"What about more enjoyable activities in the bedroom?"

"I told you, a gentleman doesn't expect sex on the first date. Now come here and cuddle with me while we argue for the next 20 minutes about what to watch." She laughed as she sat next to him, retrieving her mug before settling flush again his side. She could definitely get used to this.