Author's Note: Hello dearies! I have been enjoying all the wonderful CS stories posted here on Fan Fiction so much that I was inspired to start a new one. For those of you following my other story, Enchantment Restored, rest assured that I have not abandoned that, but this story would not leave me alone. I was trying to explain the extremely complicated Charming family tree to my husband one night, and got to thinking, how awkward would the Milah/Killian/Emma situation be in a modern time period? I love writing relationship stories, and my imagination ran with it. I hope you enjoy the story. If so, please consider leaving me a review or sending me a PM. I love getting feedback on my stories.

Disclaimer: I don't own these characters, just the fanciful workings of my imagination.

Chapter 1

"Swan!"

Emma jumped when she heard her friend Mu call out her name. She had been lost in thought as she sat at her desk, having a slow day. She had started working at Grumpy's Bail Bonds nearly two years ago, and spent most of her time doing administrative work: helping with contracts, filing, and managing the books. Working at a bail bonds agency had a lot less excitement than what was portrayed on TV.

'Mu' was short for Mulan, but she hated using her full name, thanks to her Disney counterpart. Mu liked to remind everyone that she was born a full 8 years before that movie came out and was named after the legendary Chinese warrior, not a Disney Princess. The woman was a few years older than Emma, her features reflecting her Chinese heritage, and enhanced by her purple hair and tattoos. Mu's short stature did nothing to reduce the intimidating air she gave off as she leveled her gaze at Emma now.

"I figured you were wearing earbuds by the way you ignored me," Mu said.

"Sorry," Emma replied. "I guess I got lost in thought. I was thinking about how dull this job is compared to what we see on TV shows."

"Well, that's because you haven't been out with me to chase a skip yet. But that's all about to change. You have a date tonight."

"What?" Emma asked, confused.

"This one likes hook ups. His history showed he likes blondes, so I put your pic up on Tinder. He wants to meet you tonight."

"You used my picture as bait?!"

"Relax!" Mu said. "I'll be there the whole time. You only have to go in and keep him occupied. I'll come up and cuff him from behind. Do you have anything slutty to wear?"

Emma was flabbergasted. "I don't know about this, Mu."

"Come on Emma! You need to learn how to do this sooner or later. The payout is way better than desk duty. I'll split tonight's take with you 50/50 if that will make you feel better."

Emma was uneasy with this plan, but Mu was right that she would need to learn this sooner or later. It had been hard to find a decent-paying job after her stint in jail, and she needed to start picking up skips if she ever hoped to have enough money to give her four-year-old son, Henry, the life she felt he deserved. She took a deep breath and said "okay."

"Great!" Mu said. "Do you need me to see if Aurora can watch Henry?" Aurora was Mu's girlfriend. They met in college, finding an immediate connection through their Princess-style names.

"Maybe," Emma replied. "Let me see if Regina can get him first. He's already got things over there and he and Roland are like brothers."

Emma's time in jail came after she was arrested for cocaine possession. She and her boyfriend at the time, Neal, had never done anything more extreme than some underage drinking and pot smoking, and even those cases were very rare. Emma hated the feeling of being out of control, and tended to stay away from drugs for that reason alone. She had no idea that Neal was dealing. Unknown to her, he'd hidden some of his stash inside her suitcase. He disappeared two days before the cops came to search the apartment. After their search, they'd asked Emma to identify if the suitcase was hers, and she stupidly did. They arrested her and pumped her for information about the supplier. Though she didn't know anything, she was sentenced to two years with credit for time served. She'd learned of her pregnancy shortly after her arrest. Unable to contact Neal, and having no family to speak of at the time, she'd had no choice but to let her son go into the foster system until she could finish her sentence. She was extremely reluctant for her son to be a foster child, remembering her own bad experiences, and she begged the Social Worker to find a good situation for him. He'd been placed with Regina, and lived the first two years of his life with her, until Emma was released, able to get a job, and set up a stable home.

After being reunited with her son, Emma realized she had no help. Regina offered to step in for Henry's sake. Regina was…prickly, to put it lightly, but she did truly love Henry. She and Emma were slowly starting to build a good relationship. It helped that Regina had recently married Rob, a man she met when Henry and Rob's son, Roland, were in daycare together. Rob was a widower whose wife died in childbirth. He and Regina began dating when the kids were a little older than two, and just married in a small ceremony about 6 months ago. Emma liked Rob, and though they were only a little more than 10 years older than her, in their mid-30s, Emma looked up to Regina and Rob as her surrogate parents.

Henry and Roland were very close in age and greatly enjoyed each other's company. They still attended the same daycare and had playdates nearly every weekend. It was not uncommon for Henry to spend the night at Regina's, though Emma usually did nothing with those free nights but sit around her small apartment and binge watch shows on Netflix.

She picked up the phone to call Regina and explained the situation. Regina said she was happy to help, and offered to let Henry sleep at her house and drop him off at daycare in the morning. Emma was grateful and said she would call to talk to Henry before the boys' bedtime.

With that out of the way, she returned to the situation of what to wear on her date. She didn't have anything slutty to wear, so Mu decided they needed to go shopping.

"I don't really have the money for a dress," Emma said.

"No worries," Mu replied. "I'll put it on my credit card. I'd consider this a work-related expense."

Emma knew better than to protest. She figured that whatever dress she got would definitely not be worn again unless they had another job like this one, so it was justified as work-related expense.

A few hours later, Emma stood in the back of the office, wearing a skin tight pink dress and black heels that were higher than any she'd worn before. In addition to buying the dress and shoes, Mu had dragged her to a salon for a blowout, which left her long hair hanging in soft waves down her shoulders. They'd finished the transformation by Mu dragging her to an empty office that served as a break room, saying it had the best lighting, in order to apply makeup. Emma had never worn this much makeup in her life. Her green eyes were rimmed with black liner in a cat eye shape that was just thin enough to not be garish. Her lips were accentuated with a soft pink color that emphasized their shape and made her face glow. As she looked in the mirror Mu held up, Emma couldn't help but feel pretty.

"Hot," Mu said. "I'd bang you if I were single."

Emma blushed involuntarily. "Thanks for the compliment," she said with sarcasm.

"Remind me when we get there to take a few pictures of you before we catch the guy. It will be useful if we need to pull this Tinder sting again."

They headed out to Emma's car, an old, yellow VW Beetle and the only thing Neal knowingly ever gave her. She was surprised she got to keep it once she was released from jail. She and Neal met when she was attempting to steal the Bug, which he'd already stolen. He must have gotten a clean VIN for the car, because when she got out, the keys were returned to her. Despite the bad memories from Neal, Emma loved this car. It probably wasn't the best family car, but it was reliable and had been a huge help when she was trying to rebuild her life.

Once at the restaurant, Mu and Emma reviewed the plan one final time and headed inside. Mu wore a beanie over her purple hair, and kept her distance several paces behind Emma. Emma spotted her target at the bar and walked over to him.

"Hi," she said, putting on her most charming smile. "Are you Jack?"

"Yes," he replied, returning her smile. "You must be Emma. I have to say, I'm somewhat relieved."

"What?" she said demurely. "You thought I lied on the app?"

"Well, truth be told, your profile pic doesn't do you justice."

She put her hand on his arm and leaned in a bit closer. "Same to you."

He winked at her, and Emma felt a rush of adrenaline. This was actually kind of fun. She continued to talk with Jack while they ordered drinks. The plan was for her to maneuver him to a secluded corner table that Mu picked when she scouted out the place, but Jack was proving resistant to moving from the bar. He seemed to want to show Emma off to the other men there, which made her want to scoff in disgust.

When Jack turned away to order more drinks, she let her eyes wander around. They landed on a man across the bar who was almost too good looking to be real. He had dark hair and lightly tanned skin. A scar was on his right cheek, just above the dusting of a copper-tinted beard along his jaw. Even in the dim lighting, she could see that his eyes were a brilliant blue. Though he was sitting, she could tell he was tall and muscular, and his body language exuded confidence. He met her eyes and held her gaze, raising his right eyebrow in a curious gesture. She had to stop herself from responding with a smile, remembering that she was supposed to be here with Jack. Tearing her eyes from the delicious-looking man, she refocused on Jack, who thankfully had not noticed her distraction.

Eventually she got Jack into the corner, and Mu came up and cuffed him, just as they planned. Mu told Emma that it would be better if she took Jack to the police station in the Bug and then came back for her. Emma agreed and wandered over to the bar. She was perusing the menu for something to eat when she felt someone walk up behind her.

"That was not how I expected your evening to end, love."

A shiver ran down her spine and she turned to see Captain Delicious. In addition to his amazing looks, he had one of the sexiest accents she'd ever heard. She tried her best to school her features and not give away her attraction.

"Well," she began, "I like defying expectations."

He smiled, and his whole face lit up. He gestured to the empty stool next to her. "May I?" She inclined her head and he sat down.

"So," he said, "were you in on that performance?"

"Yes. I work with the woman who took him away. She's my friend and she's training me."

"You work as a bail bondsman?"

"Bondsperson," she corrected. "Although I'm not licensed yet. Mu is starting to teach me how to catch skips while I prep for the license exam. Mostly my days are spent at the office doing admin work."

"I see. Could you tell me your name? Or would that blow your cover?"

She smiled. "Emma. Emma Swan."

He extended his hand and she took it. As they shook hands he said, "Killian Jones, at your service."

"It's nice to meet you, Killian."

"And you, Emma."

"So, Killian, what do you do to earn a living?"

"I'm a professor. I teach History at Storybrooke U."

"Interesting," she said, dragging the word out. "How long have you been doing that?"

"Well, in my younger days, I was in the Royal Navy. But I never saw myself as a career soldier, so when my time was up, I got out. I spent some time traveling with my brother, and we went diving on shipwrecks. I started a blog about our travels, which turned into a book deal. Then I took the money from that, went back to school, and too many years later, ended up with my PhD in History. My specialty is Maritime History, but I mostly teach World History now."

"A PhD? So you're actually Dr. Jones?"

He laughed. "Only to my students."

Their conversation continued, and Emma found herself truly enjoying the exchange. But all too soon they were interrupted by Killian's phone ringing. He looked at the screen, frowned, and silenced the ringer.

"Apologies, love. I need to make my exit. I unfortunately need to go have an unpleasant conversation."

"Is everything alright?"

"Nothing dire. I just need to go talk to my sometimes girlfriend. She's been a bit hot and cold lately."

Emma's heart sank a little. Of course a gorgeous guy like him would have a girlfriend. She put on a smile that didn't quite reach her eyes as she extended her hand and said "It was really nice meeting you, Killian."

"You too, Emma. I hope I can see you again. Do you come to this bar often?"

She shook her head from side to side. "This is my first time here."

He fished out his wallet and placed one of his business cards on the bar in front of hers. "Well, if I can ever do anything for you, please reach out to me."

"Thanks," she said, unable to hide her disappointment at his departure.

He put a hand on her shoulder and winked at her. Even that innocent touch was enough to fan the flame inside. He seemed to realize this, smirking as he walked away without another word. His arrogance helped her overcome her attraction, and she scoffed out loud.

She put his card in her purse, finished her drink, and closed out her tab. When she stood to leave, Mu was there with a happy look on her face.

"All done!" she said. "Leroy will get you your cut tomorrow. Let's head back to the office so I can get my car. I need a hot shower."

"Sounds great," Emma said, following her friend out of the bar.

The next day started well, with Emma collecting her payout and finding herself $500 richer. She was tempted to spend it all on something frivolous, but she decided it would be better to save it. Nearly all of it went to her savings account, but she did set aside $50 to take Henry to do something fun that weekend.

After that she quickly finished the paperwork she had waiting, and gave a client a ride to court. When she got back it was lunch time and she was out of things to do. Mu was out, and she didn't feel like studying, so Emma decided to work on her personal project of trying to track down Neal.

Emma would be perfectly happy if she never saw Neal again, but she knew that wasn't fair to Henry. He was starting to ask questions about his father. Emma had considered lying and saving her son some pain, but Regina counseled her against it. After considering Regina's advice, Emma had told Henry that she didn't know where his father was, but that she would do everything she could to find him so they could meet.

The trouble was, Neal Cassidy was hard to find. There was no record of him in Boston. It was a fairly common name, but every lead she tracked down was a bust. After a while, she was beginning to lose hope. Luckily, her friend David, a police detective, had offered his services to help as well.

Emma met David through his wife, Mary Margaret, a teacher at Henry's daycare. Mary Margaret was quite possibly the most upbeat person Emma had ever met, but she was so genuine that you couldn't help but like her. David was not quite as chipper as his wife, but still annoyingly positive. They were good people, however, and Emma was happy to have their help. She hadn't heard from him lately, but still felt it couldn't hurt to call.

"David Nolan," he answered when she called his cell.

"Have you still not saved my number in your phone, Dave? Or are you just messing with me?"

"Nope, still haven't saved it. I like the mystery of not knowing who's calling me."

"You're weird," Emma replied.

"I'm glad you called. I was meaning to call you. I got a lead on your project."

"You did?" Emma was cautious. She'd run into so many dead ends in this search.

"Yeah. I came across some arrest records from about 15 years ago. A kid gave the name Neal Cassidy at arrest, but his real name was Neal Gold."

"Of course!" She exclaimed. "He gave me a fake name. I'll add that to the list of lies he told me."

Well, the trail runs cold there, but he was picked up by a woman named Milah Gold. She was listed as his mother."

"Milah Gold...I'll look her up. Maybe I can find her and get to Neal that way. Thanks Dave!"

"Happy to help. Oh, and Mary Margaret mentioned having you and Henry over for dinner Friday night. You in?"

"Sure. I'll let her know when I pick up Henry this afternoon."

"Great. See you then, Emma."

Emma hung up, feeling refreshed. She immediately began searching for more information about Milah Gold, and the search was immediately fruitful. Milah owned a small boutique in a trendy part of town that sold vintage clothes. Emma decided to pay the boutique a visit that afternoon, before she lost her nerve.

She parked a few blocks down from the boutique, in the first open spot she found. Taking a deep breath, she began to walk to the store. Unfortunately, she wasn't paying attention where she was going and ran right into a man carrying two cups of coffee, which were spilled all over her white shirt.

"Fuck!" She cried out. The coffee wasn't too hot, thankfully, but it stained her shirt and her bra was now clearly visible under the wet fabric. She looked up, ready to chew out the offender, when she recognized his blue eyes.

"Emma?" He asked before she could say anything.

"Killian...hi," she replied, giving him an awkward smile.

"I didn't expect to see you here."

"I could say the same."

"I'm here to-" he started, but was interrupted by the shop door opening and a beautiful, somewhat older, woman with flowing brown hair stepping out. She was taller than Emma, and looked to be somewhere in her 40's. But even with her age, she was stunningly beautiful.

"Killian?" The brunette asked. "Is everything alright?"

"Milah," he replied. "I'm afraid there was a bit of a mishap with our coffees." He pointed to Emma.

"Oh no!" Milah replied, taking in Emma's soaked shirt. "Come inside dear. I am sure I can find you something to replace the shirt my boyfriend so haphazardly ruined."

It took Emma a moment to connect the dots. "Milah?" She asked. "Milah Gold?"

Milah stopped and stared at Emma. "Yes...and you are…?" Her tone was wary, but not unkind.

Killian stepped in. "This is Emma Swan."

"You know each other?" Milah asked. "Are you one of Killian's students?"

"Um...no," began Emma. She remembered Killian mentioning there was some tension with his girlfriend, and she chose to take his lead on this.

"Emma and I met the other night at Tony's. She had some trouble with her date."

Milah smiled, but there was definitely some jealousy there. "Always the gentleman."

She led Emma inside and found a shirt for her. She led the younger woman to the changing room and Emma gratefully replaced her shirt with the much nicer sweater. She tried to pay Milah for the item, but Milah refused, saying she would put it on Killian's tab.

"So," she said after Emma was cleaned up. "What brings you here?"

Emma sucked in her breath. This was awkward, but she would not back down. She hated disappointing her son.

"Do you have a son, Neal?"

"Yes…" Milah said.

"He and I used to date. I haven't heard from him in almost five years, but I really need to talk to him."

"Why?"

"Well, you see, he and I have a son together. Neal doesn't know about Henry, but I want my son to have the chance to know his father."

"Neal has a son?" Milah asked. "You mean to tell me that I'm a grandma?"

"It would appear so," Emma responded. She took out her phone and showed Milah a picture of Henry

"Oh," Milah replied. "He looks just like Neal did as a boy."

"Do you know where I can find Neal?"

"I'm sorry, no. I haven't spoken to my son in ten years. We're not on the best terms. Maybe Robert can."

"Robert?"

"My ex-husband." Milah replied. "He's a lawyer, but he also teaches at Storybrooke U."

"With Killian?"

"Different department, love," Killian chimed in. "He teaches contract law."

Milah seemed to have forgotten Killian was there. She stepped closer to her boyfriend and looped her arm with his in a clearly possessive gesture.

"I don't like talking to Robert, but I agree that Neal should know he has a child. I'll reach out to Robert. Could you come by again on Saturday, maybe around 10? I should have an answer then. And maybe you could bring my grandson? I'd love to meet him."

Emma was unsure, but decided to continue on this path. Milah was obviously insecure about her relationship, but she figured it couldn't hurt for Henry to get to know another family member.

"Okay," she said. "We can do that."

"Great!" Milah said. She picked up a business card from the holder by the register and circled her cell phone number. "Call me if anything changes. I can't wait to meet Henry!"

Despite Milah's territorial behavior, Emma could see she was truly was excited about meeting Henry. She gave Milah a warm smile and said goodbye. Just then a customer came through the door, carrying a box of clothes. Milah indicated this was a client who was selling some pieces, and asked Killian if he would go get new coffees for them. They gave each other a chaste kiss and Killian followed Emma out the door.

Killian and Emma stood awkwardly looking at one another, just outside the store's entrance. Killian began nervously scratching behind his ear before saying "she's a good woman, Milah is. She's had a hard go of it, but she's got a good heart."

"Good to know," Emma said. Even now she couldn't shake the attraction she felt toward this man. He now had his hands in his pockets, the muscles of his forearms flexing as they peeked out from his rolled up shirt sleeves. She caught herself staring a moment too late, and looked up to see him with that damn eyebrow cocked up again.

"I have to go," she said as she felt her cheeks turn crimson. "See you around Killian."

"You too, Swan."

Emma got in her car and berated herself. What was she doing? This man was dating a woman she'd just learned was her son's grandma. Was she really lusting after a man who was, for all intents and purposes, Henry's step-grandfather?