an: In an attempt to write a Single Mom!Emma oneshot, I ended up unearthing this prompt, which subsequently brought me to the inevitable conclusion that I needed to write it to it's fullest potential. So, instead of writing the fics I had intended to write, I've started to write this instead, and I hope it's an enjoyable ride for you, because so far, I'm having a blast.


Her apartment is small.

There's one bedroom, a bathroom, and a tiny living space that joins together the living room with her kitchen. Her stove works only twenty-five percent of the time, and her fridge smells like a skunk died in it. There are cracks in the walls and the sink in her bathroom often drips.

And her neighbor, one Killian Jones, enjoys a number of things, including, but not limited to: listening to incredibly loud music, banging his headboard against the wall between their bedrooms any given time between the hours of one and six in the morning any given night, and setting the smoke alarms off in the building at two in the morning.

She'd met this devastatingly handsome man two weeks ago, the morning she and her small son, Henry, moved into the building.

He'd come rushing to her aid, claiming she was in need of some muscle, and tried helping her with her mattress as he told her his name. She not-so-accidentally stepped on his bare toes in the process of telling him hers.

To say they're enemies would be accurate, she thinks.

Henry is officially one, and he keeps things interesting for her during her off-hours while she's at home. She chases him all over her apartment some nights when he gets hold of her phone and won't let go.

He's a good boy, though. He's handsome as they come, and despite the occasional frustration, he's made being a single mom fairly simple.

"Henry," she sighs.

He's crying for her and it's barely seven in the morning on her day off.

Emma pushes out of her bed and drags her fingers through her hair so she can pull it up into a ponytail before she leans over her son's crib.

He sobs at her for a few seconds and she pulls him out, settling him onto her hip. His lower lip trembles, but as she kisses his forehead, his cries soften into a hiccup. He sticks his fist into his mouth and leans against her.

"Well, good morning to you too, monkey." She leaves a few kisses to the side of his head and shuts her eyes as she breathes him in.

Every day, she realizes how lucky she is to have him. She almost didn't. She almost gave him up out of the pain of reality. But the second she heard his voice she was in for it and ended up holding him and wanting him all the more.

Emma carries him out into the kitchen after changing his diaper and settles him into his high chair so she can feed him some cereal, and by the time she grabs his bottle to fill it with milk, he's crying again.

"What?" she asks, setting the bottle down on his plastic table. Henry just cries at her and she drops her shoulders in defeat. "Henry, you're going to wake the neighbors if you keep crying. Is it that tooth? Is it coming in?"

Emma leans down to check his open mouth and shrugs her shoulders at him. "I don't know what to do with you, kid. Have your milk."

She presses the bottle into his mouth and thankfully, he drinks it, but as soon as he's done, his cries return, and he refuses to even try to eat the Cheerios she'd poured out for him. She presses her hand to his forehead and checks his temperature with the thermometer, finding that he is indeed running a slight fever. He needs medicine, but they're out.

Emma lifts him out of his chair and carries him to his playpen in the living room, allowing him to continue sobbing as she goes to change into clothes for their trip to the grocery store.

She shuts off her lights before going to grab the bag she's been using for Henry's diaper stuff. She sticks some things that should keep him occupied inside and drapes it over her shoulder after shrugging on her coat.

It's December in New York City, and while she should be excited about the holiday season, she's found herself bitter about the whole idea. She can't afford to give Henry a good first official Christmas. She can barely afford to give herself anything nice every once in awhile.

Henry's still sobbing when she meets him in the living room. "Hey, baby boy, I'm sorry I can't give you any painkillers. We're out. That's why we're going to the store."

Emma dresses him in his coat and hat and leaves him in his pajama clothes because he'll probably feel warmer in them.

As she settles him onto her hip, he slows his cries, something that gives her partial relief, but he's still upset, and Emma knows there's nothing she can do but be here for him, so she hands him his teething toy and kisses his forehead as she makes her way to her front door.

There are three locks on it and one is broken. She slides the chain toward the wall and unlocks the key slot before opening the door, only to find her neighbor standing on the other side, his fist raised to knock.

His eyes widen at the sight of her and she tilts her head at him. "What are you doing here?"

"He's been crying for quite some time. I wanted to make sure everything was all right. Like a good neighbor might."

"Oh, of course, you're being a good neighbor." Emma rolls her eyes. "It's because he's teething. As we've discussed. Multiple times."

She shifts Henry's weight on her hip as she turns around to lock the apartment.

The thing about Killian Jones is he doesn't know when to quit.

He's come over to her apartment many times when Henry has burst into tears, apparently worried that she's not doing her job as his mother or something, and he always asks, at the end of it all, if she's interested in going for pizza, or to a movie, or to a bar.

She always says no. Because he's selfish and cocky and apparently he's bored, because he hits on single moms in his apartment building when he could be dating literally anyone else.

"Here's the thing, Killian," Emma says, turning around to face him again. "I'm not interested in you. So you can go back home and sleep. I have to go shopping."

Killian's brow furrows and he looks at Henry, whose cries continue in a low whimper. "Would you at least like some help? If I know anything about your boy it's that he gets clingy when he's teething and it might be hard for you to get much of anything done at the store."

Emma groans. He's right. How he knows that much about her is beyond her. "Fine." She searches his eyes for a moment. "But stop coming over. We're not friends, Jones. We're neighbors."

"I know," he smirks. He's eyeing her up and she groans again in frustration before taking the lead to the elevator. "You're adorable when you're pissed at me, Swan."

Emma doesn't have the energy to yell at him, so she just thrusts her middle finger up at him and keeps walking.

He laughs and jogs up beside her.

After pressing the down button on the elevator, she turns to look at him. "Why is it that you think weaseling your way into my business with my kid is going to get you anywhere?"

Killian arches an eyebrow and sticks his tongue into his cheek before dragging it over his upper lip. "I'm not one to back down from a challenge, Swan."

She gives him a look. "Yeah, well, I don't do one night stands with my next door neighbor."

He just smiles and leans in so his lips press against the shell of her ear, "Darling, one of these days you'll find yourself with an itch that needs scratching. It's only a matter of waiting out your instincts."

Emma would smack him, but the elevator doors open, and she finds that shooting daggers at him with her eyes is just as effective.

She does need his help at the store, after all. She can't risk alienating him before she can get her shopping done.


They have to take the bus to the grocery store, because their apartment is in a rather densely populated part of New York City, and Killian ends up boarding the full bus behind Emma, who cradles her son as she sits in the last available seat.

He stands beside her, holding onto the bar over her head, and she occasionally looks at him, making him wiggle his eyebrows at her so she'll roll her eyes.

She truly is adorable when she's pissed at him.

Honestly, the only reason he's so interested in Emma Swan is because the day they'd met, she'd been so adamant on not talking to him and letting him know who he'd be living next to.

She's a curious creature, Emma Swan, with her one-year-old boy, the cutest he's ever seen, and a murky history he's sure is filled with as many mistakes as his is.

Her hair is lovely, tied up into a ponytail, and she's wearing a bag over her shoulder. Henry's holding a toy in his mouth, but then he releases it and it falls to the floor of the bus. Killian, without hesitation, leans down to grab it for the boy.

Henry grins up at him, a stark contrast to the tears he'd been shedding earlier, and Emma sighs as she watches Henry stick the toy back into his mouth.

Killian catches the eye of a woman sitting in the row before Emma when the bus jolts and it causes him to shift forward, nearly sending him into her lap. She laughs with him and he winks at her.

"Apologies. I'm not usually this clumsy around beautiful women."

The girl laughs. "Right."

Emma audibly groans and he glances back at her, lifting an eyebrow, but she just turns to the gentleman sitting beside her and asks him to pull the cord for her.

"So, love, where are you headed?" Killian asks the gorgeous brunette.

She sighs. "Work. You?"

Killian glances at Emma, who attends to Henry in her lap, and then back at the woman he's chatting up. "I'm headed to work myself. I'm a lawyer."

"Oh!" the woman gasps, her brow knitting as she takes in his appearance. "What do you practice?"

Killian shrugs. "I'm a divorce attorney. I'm just heading in for some paperwork I left on my desk." He gestures down at his outfit. "And I'm the boss, so I figure dressing down isn't a bad thing."

His new friend nods her head. Her tone is dripping with desire and she drags her teeth along her lower lip. "Absolutely."

When he glances back at Emma, she rolls her eyes, and Killian looks up when the bus pulls to a stop. "Well, this is my stop. It was truly wonderful meeting you-"

"Michelle," she fills in the blank when he extends his hand to shake. She takes his hand as he digs into his pocket for his card, then he leaves it in her extended palm.

He winks at her as Emma and Henry go to the door of the bus and says, "Give me a ring sometime."

He jumps out of the bus and onto the sidewalk where Emma waits, her eyebrow cocked and a smirk on her lips. "Oh, so you're a lawyer now. I thought you were a doctor. Or was that just last week when you had what's her name in your bed?"

Killian gives her a look. "Are you eavesdropping on my seducing other women?"

"Our walls are very thin. I couldn't help it if I tried." She shakes her head in annoyance and presses her hand to the back of Henry's head as they walk the sidewalk toward the grocery store. "And you should probably stop that, by the way, because I work way too many hours to come home to hear you blasting Journey while you're finding some hidden treasure over there."

He just smirks at her despite the fact that she won't look at him. Sometimes, he likes to imagine she likes him just a little bit, but she's so guarded that she won't let him in.

He's known her for all of two weeks and all he finds himself wondering about is this woman and her infuriatingly short temper for him.

Killian grabs a cart when they walk into the grocery store and Emma continues to hold a now partially soothed Henry in her arms.

"Okay," she says. "Let's get him some baby aspirin first and then we can figure out the rest of my list."

Emma leads the way and he follows her, having a look around the shop as he does. Grocery stores are usually a playground of a sort for him, and so far, he sees at least one woman he wouldn't mind giving his number to.

"Ow! Jones, watch where you're pushing the cart or I'll regret letting you help me."

Killian looks at Emma to find that he's run the cart straight into her. She gives him a hard look and grabs the baby aspirin from the shelf.

With some difficulty, Emma works the lid off, and she holds the pill in between her fingers while she tries to feed it to her boy. Henry whips his head around a few times, keeping his lips pressed together, and Killian furrows his brow, moving toward them.

It pulls at his heart, seeing Emma and her son. He knows she loves her boy quite a bit. In the two weeks they've been neighbors, all he's seen of her is her constant willingness to try with her boy. Often, he hears her talking to her son through their wall, and it makes him smile, because the care she gives to Henry is far and above the kindest part of her.

Gently, he says, "Here, let me see if I can't do it."

Emma tilts her head to the side and her reluctance gives way when Henry starts whining quite loudly. He takes the pill from her and smiles at Henry.

"Hey, Henry," Killian says, earning Henry's attention. "It would make your mum and I quite happy if you'd open your mouth and have this medicine. It'll help your mouth feel much better, I promise."

Surprising both of them, likely, Henry allows Killian to put the medicine past his little lips, and his arms are suddenly drawn out toward him.

For a half second, there's a moment shared between he and Emma as they look at one another. He finds that she's impossibly sweet, the way she's gazing at him, as if she can't believe he actually made it happen, that he got her son to take the pill when she couldn't.

"Seriously, kid? You want him to hold you now?" Emma half-whines. She narrows her eyes at Killian. "You can't pretend he's yours and go pick up some poor innocent woman here buying cereal. Got it?"

Killian gives her a look. "Love, do I look like I'm that desperate?" Her eyebrows pinch inward and she drops her shoulders. "Okay, perhaps I am." He gives her as honest a look as he can muster. "I swear I won't."

Henry whines until Emma hands him over to Killian and when he's in his arms, Henry clutches Killian's coat tight in his fists. Emma hands him Henry's pacifier, and Henry eagerly accepts it, suckling on it as he stares at Killian with his wide eyes.

Kids have never been on his list of favorite things, but as he holds Henry in his arms, Killian finds that it isn't half as bad as he'd thought it would be.

If any of his friends or family saw him now, they'd truly think he's a reformed man, holding a baby in his arms.

When he looks at Emma, she seems to be in thought, her defenses lowered, and Killian smiles at her. "He's a heavy little guy, isn't he?"

Emma laughs. "Yeah. And he's strong, too. Watch your nose. He might steal it from you."

Killian chuckles and turns his attention to Henry. The boy reaches up to touch his face and Killian scrunches up his features at him so he'll giggle. He does.

"Okay, next stop: milk." Emma says on a sigh.

She pushes the cart forward and Killian just smiles a little at Henry. He runs his fingers up his belly until the baby starts to laugh and he laughs, too.

It's a delightful thing, helping Emma with her groceries, and he actually thinks they're making some progress.

All he truly wants is to be friends, because she's been so impossibly hard to break through to. And he thinks maybe today is his chance. After two weeks of suggesting venues for them to bond, she finally let him accompany her on this trip.

The grocery store is probably as good as it gets with her, so he'll take it.

When Killian glances up, he immediately regrets it. Up ahead in the aisle they're walking down, Killian finds someone he'd thought he'd never see again.

"Shit," he curses under his breath.

Emma gapes at him. "Hey! Watch your mouth around my baby, Sailor. He mimics now."

He tilts his head toward the couple in the aisle a few feet ahead of them and murmurs, "Darling, we should get out of this aisle. There's someone I'd really rather not see again and-"

"Who? Mr. and Mrs. Perfect over there?" Emma asks, furrowing her brow. She snorts. "What's wrong with them? Did you try to flirt with her?" His neighbor leans in closer so she can whisper, "Is it your baby?"

Killian gives her a hard look. "No. That's my college roommate and his wife. I unfriended them both on Facebook years ago because I thought that I'd never see them again."

"What's wrong with them?" Emma asks, not caring as she pushes the cart forward.

Killian reaches out to grab it, effectively stopping her from getting them any closer. He uses the kid on his hip as a human shield, but he knows it's not the best guise. "Nothing's wrong, I just…"

"Killian?" Mary Margaret Nolan gasps. "Killian Jones, is that you?"

He turns to face her, easing himself into a smile as he studies the woman. She waddles toward them quickly, her smile spread as far as it possibly can. Her eyes shine brightly and she gasps, her shoulders jumping as she clasps her hands together over her heart.

"Oh my gosh, it is!" Mary Margaret grins. She spins around and Killian glances over to find his former roommate walking toward them, a smile on his own face. "David! Look at who I found!"

David chuckles as he joins his wife. He has a few things tucked into his right arm from shopping in lieu of a cart or basket, and he's dressed comfortably for the December weather, a scarf falling from his neck and his coat unbuttoned.

It has been years since he's seen the man and he's standing in a grocery store in the middle of New York City with his expecting wife, looking at him as if he's about to pick things up where they'd left them; as if his faith in him had been so shaken that he couldn't believe that he'd ever truly see him again.

"Killian Jones." David shakes his head. "It has been, what, six years since we last talked?"

Killian shrugs, shaking his head. "It's been awhile, for sure, mate."

He smiles at the man and holds out his hand to shake. David complies eagerly. "Well, how are you, buddy?"

"Good, good," Killian nods. "You and Mary Margaret appear to be doing quite well."

He glances down at Mary Margaret's belly and David chuckles. "Yeah. We're great."

Mary Margaret, meanwhile, has a look at the situation, at Emma, who is still standing there, and at Henry, who has attached himself to Killian's hip with his small arms suddenly around his neck and his soft head of hair brushing against his collarbone.

Her eyes grow wider. "Oh, Killian! I knew you'd settle down eventually, I just didn't think it would happen so soon after…" Mary Margaret stops herself from continuing and Killian's face falls as his heart drops to his gut.

He looks at Emma and back at the happy couple standing before him, and suddenly, he's jealous of his old roommate. He's got a wife and a baby on the way, and Killian has nothing.

He can't admit to the Nolan's that he's still wallowing and broken after what happened, not now. It's been six years without contact. He hasn't been back home in ages. His own brother doesn't know what he's up to.

And he knows what David would say if he explained that he's just here to help his neighbor with her clingy child. He'd tell him "I told you so," or "You haven't changed one bit."

The thing is, he can't let David win this time. Because he'd won when Killian left six years ago. David Nolan is the very definition of his worst nightmare coming true. It's his past come back to haunt him and he doesn't want his past to consume him right now.

So he figures there's nothing to lose here except for a few awkward minutes of his life.

Killian smiles and shakes his head. He wraps his arm around Emma's middle, silently praying that she'll go along with him on this. Knowing her, she'll end up spoiling it for him.

"Ah, right, uhm... this is my wife, Emma. And our boy, Henry."

Mary Margaret smiles wider and when Killian meets David's gaze, his friend has a pleasant look on his face.

"It's nice to meet you, Emma," Mary Margaret says, holding out her hand. Killian's hand falls to the small of Emma's back and she hesitates for a moment before reaching out to shake Mary Margaret's.


"Darling, this is Mary Margaret, and her husband David. He was my college roommate. I've told you about him."

Emma nods her head and laughs, suddenly in the spirit of things. "Right. Hi."

She shakes David's hand and then settles her hands on the cart.

Killian looks between his former friends, wanting nothing more than to get out of here, but Mary Margaret is eager to continue bombarding them with information.

"We're just here for the weekend," she explains. "It's kind of a babymoon. We're due in a month and we wanted to get away for a bit before the Christmas chaos. Storybrooke is nice, but we wanted to check out New York City. What a nice surprise, getting to see you again."

Killian smiles at her as her hand falls to the curve of her bump. "Aye. A real delight. I was just wondering about you the other day and how you were doing."

"Well, if you'd come home for the holidays, maybe you'd know," David teases, chuckling.

Emma cranes her head to look at him and he meets her eyes, finding them alight and up to something. She shrugs her shoulders and shakes her head. "Sorry about that. It's my fault. I keep him pretty busy at home."

Killian's smile spreads softly in amazement, that she'd actually dive in and do this for him, and he gives David and Mary Margaret an apologetic look in return. "What can I say? I'm a family man now."

He turns his attention to Henry then, finding the boy sitting up on his hip again instead of lying against him. Henry smiles at him from behind his pacifier and Killian chuckles, letting his fingers dance up his chest until the boy giggles and curls his hands up toward his much larger one.

"Well, that is the best news," Mary Margaret says in her hopeful tone. Killian looks over at her.

David smiles a little. "Hey, listen, we're only in the city until tomorrow morning. Maybe you'd like to get together for dinner? Reminisce about old times?"

And while he knows he's pushing his luck, David and Mary Margaret have silently been judging him this whole time.

Killian laughs. "You know, that would be great. Emma and I hardly get out anymore thanks to this little guy."

Emma nudges him in the side and he meets her frantically wide eyes. "Um, honey, I have that thing tonight."

"Oh, no, darling, it's fine. We can reschedule that. My friends are only in town tonight."

She turns back to them and smiles. "It's just that our puppy has been kind of sick lately and I'm worried about-"

Oh, so this is how she's playing it.

"Sweetheart," Killian sighs, shaking his head. He nudges her side. "Spot is going to be just fine. I can have the vet come over when we finish shopping."

Emma narrows her eyes slightly at him. "Yes, dear, but what about the tickets to Broadway we had tonight?"

Killian scoffs. He drapes his arm around her shoulder. "Believe me, Emma, we can get tickets for another night. My friends are here for only tonight. I want you to finally meet them."

He watches her carefully as she turns back to them. She shakes her head. "Well, dinner it is."

Mary Margaret gasps happily. "Wonderful!"