She wasn't entirely sure when she began doing it. Probably somewhere between when she first stopped trying to kill Emma Swan and when they kind of maybe became hesitant friends after the entire Neverland debacle. It was hard to hate someone when you spent a week trapped on a ship and then on an island in close proximity, with only softly whispered truths and stories to keep each other company in the dead of night.
It started small enough, when Regina realized the Savior's kindness towards her was getting Emma attitude from other Storybrooke residents. Emma would never show it, of course, but Regina saw the subtle tightening of the blonde's shoulders and the clench of her jaw whenever someone made a snide comment about her newfound trust in the Evil Queen.
The first time Regina acted, it was with a tiny flick of her wrist, magically sealing Whale's lips shut as soon as he sneered in Emma's direction with insults ready on his tongue. His eyes landed accusingly on the Queen where she sat innocently at her usual table in Granny's Diner, but one warning glare from her was all it took to send him stomping out of the establishment. Emma just watched him leave, bafflement on her features. When she noticed Regina's gaze, she smiled thinly and waved her hand before returning to her coffee.
That was the extent of Regina's involvement for about a week. When Leroy noticed Emma waving to Regina one morning and began ranting at her about choosing her friends more wisely, Regina flicked her wrist and sent him into a coughing fit. When Michael and his children entered the diner one evening at the same time Emma had joined Regina and Henry for dinner, Regina magically knocked his soup over onto his lap after he'd muttered loudly about the Savior and the Evil Queen looking too friendly.
It should have been enough, that she was helping make her life slightly easier. It was hard to ignore the guilt that roiled around in her belly every time she noticed Emma looking anything less than happy, however. Every frown, every flash of hurt in those green eyes, every forced smile made Regina wish she could do more, help more. She owed her that, didn't she? After the life Emma had been through? She may not have put the blonde in the wardrobe but she'd certainly played a huge role in that entire mess.
The next thing she began doing was lessening the paperwork. To be entirely honest, half of the work that the Sheriff usually found herself buried in was unnecessary. Regina had, as Mayor, been doing everything in her power to make Emma's life difficult. Now that she cut back on the unneeded paperwork, Emma took notice and seemed hesitantly optimistic. She showed up at town hall one day with a kale salad and a rootbeer, and an almost shy smile that had Regina's heart doing a little flip.
"There's been a lot less paperwork to get through," she'd said casually, sliding the items onto Regina's desk like a peace offering.
"Well, I've decided to streamline the process by cutting down on paperwork. Makes life easier for both of us," Regina hedged, maintaining a stoic facade. Emma's lips just quirked into a tiny grin as she waved goodbye and all but skipped out of the brunette's office.
By the third week, pastries began mysteriously appearing on the Sheriff's desk every morning. Emma first assumed it was her father leaving her treats, but when she finally opted to hug him as thanks, he'd just tilted his head like an overgrown puppy, confusion in his gaze despite being happy that he was receiving any form of physical affection from his daughter.
"So it wasn't you?" she'd asked, a bearclaw held half-eaten between her sticky fingers. David smiled in amusement and shook his head.
"Nope. But if you find out who it is, tell them that your Deputy wouldn't mind finding free donuts on his desk either."
Emma spent the rest of that week trying to figure out who her secret supplier was. Henry seemed jealous that she was being provided a steady pastry fix after reminding her that it definitely wasn't him - his weekly allowance wasn't nearly enough to treat her to a donut every morning. Mary Margaret thought the gesture was adorable and insisted that Emma must have a secret admirer. Ruby swore the pastries didn't come from Granny's Diner, but she was never a great liar and despite Emma's attempts to suss out an answer, the lanky brunette just pursed her lips and swore secrecy, insisting that she only had a hunch and refused to say anything more.
Eventually the blonde gave up, deciding to simply enjoy the free treats until her "secret admirer" revealed themselves.
By the second month, other things began happening. She'd gone to Granny's for lunch one day, sneezing and sniffling from a mild cold, and returned to find a bottle of cold medicine on her desk. David swore no one had entered the station all day, and after they combed through their security footage and found nothing, they let it go. When she'd left town hall after a long meeting and whined to herself about needing a serious coffee fix, Ruby appeared at the station with a coffee-and-lunch delivery, claiming ignorance as to who made the order and paid. When she was walking Henry home from school and shivered briefly as a breeze blew by, the wind carried with it a red scarf that flew through the air and collided softly with her face, conveniently wrapping itself around her neck. (Henry had looked at it as if it were possessed, but it looked clean and smelled of fresh linen, so Emma ended up keeping the scarf and wearing it often.)
The most notable change was the food. Henry began showing up with tupperware every other day; fresh sandwiches, hot soup, even the famous lasagne with red pepper flakes. When Emma asked why Regina was deigning to feed her, he'd just shrugged with a baffled look and relayed, "Mom said you eat like a child and need a better diet if you're going to be Sheriff. Here's our leftovers from last night." Emma didn't bother pointing out that Regina knew how to cook for two and couldn't possibly accidentally make so many leftovers all the time.
"Madame Mayor," the blonde nearly shouted with glee when they walked by each other on the street one day.
"Sheriff Swan," Regina said with an amicable smile.
"Just wanted to say thanks for sending over food all the time." Emma had that shy looking grin again and she actually toed the ground with the tip of her boots.
"No thanks necessary. We had leftovers and I figured it was advantageous to keep the town's Sheriff well fed."
"Well, I appreciate it nonetheless. You're literally the best cook in the world."
Regina actually blushed under the praise and Emma beamed, nodding her goodbye as she continued on down the street. She was only a few paces away when the brunette spun on her heels.
"Yeah?" Emma spun back around to smile at her, green eyes bright and more cheerful than they'd been all day. Regina found herself stuttering only slightly.
"Would you like to join Henry and I for dinner tomorrow night? Say 7PM? My cooking is far better when it's fresh."
Emma's smile grew wider than she thought possible. The blonde actually bounced a step towards her in excitement and Regina's heart nearly stopped, misinterpreting the motion as a hug. To her relief, Emma just leaned over and bumped her shoulder with her own.
"I'd love to, thanks. See you tomorrow then!"
With that, the blonde flounced off. Regina returned to her office, flustered. They somehow managed to bump into each other three more times before the next day's dinner.
By the third month - and a growing number of "family dinners" later - Emma found a single yellow rose on her desk. David was once again flummoxed as to how it got there (he'd spent the entire day playing darts from his desk in front of the Sheriff's office window, after all) and asked aloud whether or not he should be concerned that someone was leaving stalker-ish gifts for her.
"It's kinda sweet," Emma admitted, grinning sheepishly as she twirled the rose between her fingers, careful not to prick her fingers on the thorns. David squinted at the rose and made a face.
"It's yellow. Is that different than red roses? Does it mean it's not romantic?"
"I dunno." Emma shrugged, using her free hand to stroke the velvet-soft petals. "Yellow's my favourite color."
"Well…" David rubbed at the back of his neck, at a loss for what to say. "If you figure out who it is, tell them I'm gonna have a talk with them."
Emma laughed. Their father-daughter relationship was weird and awkward at best but he was trying his best, and she didn't mind the effort. "Sure, dad."
She ended up carrying the rose around with her that day, after cutting off most of the stem and sticking it into the breast pocket of her red leather jacket. Mary Margaret thought it was sweet and gushed about how she wanted to be the first to know when Emma discovered who her secret admirer was. In truth, Emma was watching everyone around her for their reactions to her wearing the rose, proudly on display.
"You're such a sap," Ruby said when the blonde strolled into the diner for her usual mid-day grilled cheese and hot cocoa.
"Well maybe if you told me about your hunch, I wouldn't have to resort to such measures to figure out my secret admirer."
"Nuh uh. My lips are sealed. I enjoy being alive, thanks." The waitress set down her order and scurried off, leaving the blonde alone at the counter. Emma rolled her eyes and took a gulp of her drink, looking up only when her spidey-senses tingled, alerting her to a certain Mayor's presence.
"Sheriff Swan," Regina greeted politely, eyes flickering to the rose at Emma's chest before flickering away again.
"Madame Mayor." Pleased, Emma fingered the flower at her chest pocket. "Like my rose?"
Regina glanced at it again, this time with an air of casual indifference.
"It's lovely, dear. I take it this is from your secret admirer that everyone keeps talking about?"
"Mm hmm," Emma nodded. "I'm a little disappointed it's not a red rose, though."
"Oh?" The brunette flagged Ruby down for her usual without paying too much attention to the blonde. Emma bobbed her head again.
"Well, if it were a red rose, that'd mean my admirer was interested in me romantically, right? But I guess this just means they want friendship or something?" Emma let loose a sigh, as if she were truly dismayed that she didn't have a potential date in the future. Regina side-eyed her.
"Perhaps they chose yellow because it's your favourite color, dear. Like that yellow death trap you call a car."
Emma visibly perked up, ignoring the jibe at her Bug. "So you think this means they might like me? As more than friends?"
Regina cleared her throat almost uncomfortably. "Perhaps. You seem terribly optimistic about your secret admirer, Miss Swan. You don't even know who it is. What if it's someone you're not interested in?"
Emma bit the inside of her cheek to avoid blurting out the first thing on her mind; that if Regina were behind all this, then hell yes she was interested. But there was no way it could be Regina - if only she were so lucky - so she held back her disappointed sigh and just shrugged her shoulders.
"I wouldn't know until I met them, right? Anyway, even if I wasn't interested, I'd still like to… I dunno, make a friend? They seem sweet. My favourite donuts, coffee and lunch deliveries, my favourite color - I don't even know where you'd buy a yellow rose around here."
Regina gave a small grunt of acknowledgement, accepting her to-go coffee from Ruby. The younger brunette eyed both women and didn't scamper off until Regina sent her a warning glare.
"Well, perhaps they'll reveal themselves to you one day," Regina finally said, pushing away from the counter with her coffee in hand and an amiable smile on her lips. "Dinner tonight, Sheriff?" she added casually as she gravitated towards the door. Emma bobbed her head with a smile.
"Sure. See you later, Regina."
Emma showed up at Mifflin Street later that evening with her scarf tucked neatly around her neck and her yellow rose still in her breast pocket. When Regina answered the door in her typical black slacks and pressed white dress shirt, her eyes faltered at the sight.
"Did you walk over, dear?" she questioned as the blonde hung up her coat and scarf.
"It doesn't seem cold enough outside to warrant a scarf today."
"It's my lucky scarf, I like wearing it around," Emma admitted with a sheepish smile and a lift of her shoulders. She gave the hanging scarf a little pat before following Regina towards the kitchen.
"Lucky scarf?" Regina echoed with an arch of her brow.
"Mmhm." Emma automatically grabbed the plates and cutlery to set the table, moving with ease around the kitchen after countless dinners at the Mills household. "Carried on the wind and attacked my face one day. It was clean and soft so I decided to keep it. I guess you could say…" her lips twisted with a wicked smile, knowing her next phrase would annoy the shit out of Regina. "... it found me."
Regina nearly squawked with disgusted indignation. Emma cackled.
Another month went by and still Emma was no closer to finding out who her secret admirer was. The donuts continued appearing on her desk, the coffee and lunch deliveries came every so often, and the rest of Storybrooke no longer gave her guff for being friends with Regina - a welcome relief, as she had dinner at the Mills household nearly every other evening now, along with wine on the back porch after Henry went to bed, long nights of conversation in which Emma and Regina found themselves divulging more and more of their pasts, the good and the bad. (Emma liked to tease the brunette often nowadays with "You're my best friend, ain't no choice," and Regina would just scoff and roll her eyes and pretend not to know her at all.) All in all, life in Storybrooke had smoothed out for the Savior, perfected by having loving parents and friends and a son, and for that she was immensely grateful.
Up until Mary Margaret announced that she was pregnant.
Later, Emma would understand that her parents had tried to reassure her to the best of their abilities, but at the time, no one could blame Emma for having a perfectly human reaction to the news. Jealousy and bitterness had thrummed through her veins, anger so potent and abandonment issues so suddenly raw that she somehow ended up alone at the docks in the middle of the night, a small and shivering lump on the bench.
"Emma?" Regina's warm, throaty voice broke through the cluttered mess that was Emma's train of thought. The blonde twisted around stiffly in her seat, arms tightly wrapped around herself in a sad attempt to hold in her body heat, her cheeks chapped from hours of crying.
"Hey," Emma said, praying her voice didn't sound as scratchy and broken as it felt. She swiped quickly at her face and plastered on a fake smile. "What are you doing here?"
"Looking for you. I was worried." Regina sat down slowly next to her, as if afraid that any sudden movements might spook the blonde. Emma maintained the too-wide smile.
"Worried? What for?"
"I heard about Snow's pregnancy."
"Oh, yeah. Isn't it great?" Emma beamed, averting her attention to look out onto the waters. "They've always wanted to raise a baby. I'm gonna have a younger sibling."
"You don't have to pretend with me."
"I'm not pretending. I'm happy for them, really."
Reaching out before she could lose her nerve, Regina grabbed Emma's cold hand within hers and gave it a gentle squeeze. "You're allowed to be hurt, Emma."
That fake smile finally faltered, red-rimmed green eyes glossing over with fresh tears once more. A sniffle followed, Emma's shoulders trembling in her attempts to keep her breathing under control.
"I'm supposed to be happy for them," she whispered, voice cracking. "But I-- I can't. It hurts. I'm angry and bitter and it feels like a slap to the face, like they're replacing me because I'm not the perfect little girl they wanted to raise. I wish… I wanted to be enough for them."
She was suddenly in Regina's arms, face buried against the thick lapel of Regina's coat as the fabric soaked up her tears and muffled her sobs. The brunette hugged her tightly, a hand stroking up and down her spine in a soothing motion, cheek pressed against Emma's head. They stayed that way, clutching to each other for nearly half an hour until Emma's cries had quieted, resting silently against Regina as the older woman hummed a comforting tune and ran her fingers through golden princess curls. When Emma finally tried to straighten up with an apology for sobbing all over her, Regina just shushed her and tightened her hold, refusing to let her go.
"You can stay with Henry and I, if you don't want to go back to the loft for a while," Regina murmured, idly twirling a strand of Emma's hair between her fingers. The blonde turned her head so that her ear was resting against Regina's chest, able to hear the soft beating of the brunette's heart.
"But Mary Margaret won't--"
"It doesn't matter what she wants," Regina interrupted. "You need to take care of yourself first. Your feelings matter, Emma. You can't keep suffering just to make other people happy. I'll make up the guest room for you. You're staying with us for a while, until you're ready to deal with them."
Her tone offered no room for argument, so Emma just nodded her head ever so slightly until Regina relaxed again, her heartbeat evening out.
Ba-dum, ba-dum, ba-dum.
"Thank you," Emma murmured.
"It's no trouble," came the breezy response.
"Thank you for being my friend," Emma clarified, arms tightening a little around the brunette's waist. "I… I love them, I do. But they can't always understand me. They don't know what it feels like to be rejected or misunderstood. Not the way I do… not the way you do."
Regina was silent for a while, running her fingers through Emma's hair, the blonde's breath evening out until she thought she had fallen asleep.
"You're enough, Emma," Regina whispered, heart breaking for the blonde who should never have had to feel as if she weren't enough for anyone. When Emma stirred and shivered from the biting cold a moment later, Regina reluctantly released her to dig into the pocket of her thick coat and pull out a familiar red scarf. "Here. I'm surprised you left home without it today."
Emma gratefully wrapped the warm wool around her neck. "How'd you get this? I left it at the loft."
Lowering her gaze, Regina actually hesitated and fiddled uncharacteristically with her fingers. "Can I… can I make a confession, Emma?"
The blonde was actually stunned into silence for a long minute. Regina never asked for permission to say something; she never had a problem speaking her mind at all. "Um… yeah?"
"It's me." Regina's throat bobbed with a thick swallow. Emma blinked.
"Your…" She suddenly felt foolish, admitting to be the Sheriff's so-called secret admirer. "The donuts, the deliveries, the flowers… The scarf."
"You're my secret admirer?"
"I don't expect you to feel the same way," Regina said quickly, her tone slipping into embarrassment and defensiveness. "In fact, we can just forget about it. It's no big deal. I'm perfectly content being your friend, and the offer of my guest room still stands. Henry is happiest when we get along, and I won't do anything to upset that. If you feel uncomfortable--"
Her rambling came to an abrupt halt when Emma's hands settled on either side of her face, urging her to look at her instead of turning away. "Regina."
"I spent this whole time wishing that my secret admirer was you."
"I… you… what?"
"You're my best friend, and I've kinda been falling in love with you, so believe me when I say that I'm ecstatic to know that it was you."
"B-but… Really? I thought--"
"Can I make a confession too?"
"I really want to kiss you right now."
Regina's cheeks blushed hotly under Emma's cool palms, her tentative smile mirroring Emma's, bright green eyes locked onto melting chocolate brown ones. The blonde leaned in halfway, waiting breathlessly for her response.
Regina closed the remaining distance with a gentle kiss full of promises.