Work Text:
"So let me get this straight," Henry sprawls across couch in their downtown apartment, homework assignment clutched dramatically above his head, careful not to knock over the stack of corporate security reports beside him. "I have to interview a 'female leader who's making a difference in our community' and you're telling me I can't pick Regina Mills?"
Emma nearly chokes on her hot chocolate - the special cinnamon blend Ruby keeps stocking in the kitchen with a knowing smirk. "Kid..."
"I mean, she's perfect for this!" Henry sits up, eyes sparkling with mischief as he waves his tablet, Regina's latest sustainability initiative press release lighting up the screen. "CEO of Mills Corp, ruthless business genius, probably secretly a supervillain..."
"She is not a supervillain," Emma protests automatically, trying not to think about the three separate background checks she'd run last month. For work. Obviously.
"Oh? And how would you know? Been stalking her Instagram again?" Henry grins, pulling up the Mills Corp feed where Regina stands proudly in front of their new green energy facility.
"I do not stalk her Instagram." Emma throws a pillow at him, ignoring the notification ping from her phone - definitely not a Google alert about Regina's upcoming TED talk. "I just... occasionally... for work purposes..."
"Right. Work purposes." Henry adopts an exaggerated dreamy expression. "'Oh look, Regina Mills gave another TED talk. I should watch it seventeen times. For work.' Just like those mysterious meetings with Ruby about 'coincidental scheduling'?" "
"I hate you."
"You love me." Henry flops back down, narrowly missing Emma's case files. "Come on, Ma. You could set up the interview. You're supposed to be this hotshot investigator now. Use your connections! I know Jake's dad's firm handles Mills Corp's cyber security."
Emma runs a hand through her hair, trying not to remember how Regina's voice had sounded on last week's earnings call - which she'd listened to purely for professional reasons. "Henry, I can't just call up Regina Mills and say 'Hey, my kid needs to interview a successful woman for school, mind if he asks you about your childhood dreams?'"
"Why not? You've been finding excuses to research her company for months." Henry's voice turns sing-song. "Someone's got a crush... Jake says you spent an hour 'analyzing security footage' from their last charity gala."
"I do not have a crush." Emma throws another pillow. "I just... respect her professional achievements. And that investigation was important!"
"Is that what we're calling it now?" Henry dodges the pillow. "Because last week you spent twenty minutes talking about how her business suits are 'unfairly attractive.'"
Emma groans, remembering Ruby's knowing grin. "You're supposed to be doing homework, not psychoanalyzing your mother's non-existent love life."
"Who said anything about love?" Henry's eyes twinkle. "I just mentioned a crush. Interesting where your mind went..."
"That's it. You're grounded."
"Can't ground me for speaking truth." Henry pulls out his phone. "Look, she's giving a speech at Columbia next week. We could..."
"No."
"But..."
"Henry Swan, we are not crashing a university lecture just so you can ambush Regina Mills for a middle school assignment."
Henry sighs dramatically. "Fine. I'll interview Ms. Blanchard instead."
"Your teacher?" Emma raises an eyebrow. "The one you spent all last month complaining was too obsessed with birds?"
"Well, she did turn the class hamster's cage into a bird-watching station..." Henry shrugs. "But at least she won't make you swoon like certain CEOs."
"I do not swoon!"
"Ma, you literally have a Google alert set for her name!"
"That's... that's for work!"
"Uh-huh." Henry starts typing on his phone. "Oh look, new photos from the charity gala last week. She's wearing red..."
Emma's head snaps up. "Where?"
"Ha! Busted!" Henry falls over laughing. "You're so obvious!"
"That's it, I'm putting you up for adoption."
"Too late, you're stuck with me." Henry grins. "Besides, who else would help you pine over powerful businesswomen? Aunt Ruby tries, but she's too busy making sure you don't work too late."
Emma throws her hands up. "Interview whoever you want. Just... not Regina Mills."
"Fine." Henry starts gathering his homework. "But when you finally meet her and fall madly in love, I expect to be best man at the wedding."
"There will be no wedding!"
"Keep telling yourself that." Henry heads for his room, then pauses. "Hey Ma?"
"What now?"
His smile turns softer. "You deserve someone amazing, you know that, right? Even if it's not Regina Mills."
Emma feels her throat tighten. "When did you get so wise, kid?"
"Must be all those documentaries I watch. Speaking of which..." He grins again. "Regina Mills is giving a TED talk about corporate responsibility next month..."
"Goodnight, Henry!"
His laughter echoes down the hallway. "Love you too, Ma!"
Emma waits until his door closes before pulling out her phone. There really are new gala photos, and Regina really is wearing red, standing next to an apple tree that feels impossibly familiar. Her finger hovers over the save button as another memory-that-isn't-quite-a-memory tugs at her mind - something about a blue-green dress and a mansion and...
"I heard that sigh!" Henry calls from his room.
"Do your homework!"
But she's smiling as she saves the photo. Just for work purposes, of course. Definitely not because Regina Mills in red makes her heart do funny things. And absolutely not because her kid might be a little bit right about everything.
Some crushes, after all, are worth a little teasing. Especially when your son and your best friend/assistant team up to play matchmaker. Even if they come with strange dreams and impossible memories and a nagging feeling that somewhere, somehow, this has all happened before.
Ruby's going to have a field day with this tomorrow. At least she only howls at the moon metaphorically.
Usually.
Henry Swan considers himself an expert in covert operations. At least, that’s what he's saying himself when he’s sneaking extra cookies. It’s a delicate art, really. First, he has to wait until his mom’s distracted—maybe she's on a long phone call or caught up in one of those endless "work" nights. That’s when Henry knows the path is clear.
He tiptoes into the kitchen, making sure the floorboards don't creak under his weight. The cookie jar is always on the top shelf, the one that's just out of reach. But that's no problem for Henry—he's been stretching for that jar since he was eight. Now, at thirteen, he’s got just enough height to grab it without knocking over the pile of mismatched mugs next to it. He lifts the jar slowly, steadying it with one hand so it doesn’t rattle. He carefully unscrews the lid, holding his breath for any sudden sounds that might give him away. Then, the real test—getting his hand inside the jar without disturbing the other cookies. Once he’s got the cookie, he has to pull off the getaway. No crumbs. No trail. Just a quiet retreat back to his room.
But getting himself into a Columbia University lecture hall? That's next level.
"Just act like you belong," he mutters to himself, adjusting the borrowed blazer that makes him look like a very short college student. Or maybe a very tall middle schooler playing dress-up. Aunt Ruby had helped him pick it out, trying not to laugh as she suggested he "blend in with the business crowd."
The security guard barely glances at him as he trails behind a group of students, all carrying tablets loaded with Mills Corp's latest sustainability reports. Score one for confidence and his recent growth spurt.
The lecture hall is packed with corporate types and students, their excited whispers about Mills Corp's latest green energy initiative filling the air. Henry spots an empty seat near the back, perfect for a strategic retreat if needed. His phone buzzes - probably his mother wondering why he's "studying at Jake's again." He'll deal with that guilt later. At least Jake is covering for him, probably having way too much fun monitoring the building's security feeds.
Regina Mills takes the stage exactly on schedule, and Henry instantly understands his mother's fascination. She commands attention without effort, power radiating from every precisely planned movement. The projector behind her shows graphs of educational technology initiatives, but Henry's more interested in how she seems to know exactly where every camera is without looking.
"Corporate responsibility isn't just a buzzword," she begins, and Henry actually finds himself taking notes. Not for his assignment (okay, maybe a little), but because she's kind of amazing. Plus, if his mom asks, he can say he was doing research. That usually works.
He waits through the lecture, through the polite applause, through the beginning of the Q&A. Then, summoning every ounce of Swan family audacity, he raises his hand.
Regina points to him. "Yes, in the back?"
Henry stands, channeling his best 'definitely supposed to be here' energy. "Ms. Mills, what would you tell young people who want to follow in your footsteps?"
Her eyes narrow slightly - probably noting his age - but she answers smoothly. "Success requires sacrifice and determination. But it's equally important to remain true to yourself."
"Like maintaining a work-life balance?" Henry presses. "My mom works too much too. She's actually kind of obsessed with her job. And you. I mean, your company! Your company's success."
A ripple of laughter runs through the audience of suits and blazers. Regina's eyebrow arches in that way his mother keeps calling 'unfairly attractive' during late-night conversations with Aunt Ruby.
"Your mother sounds... dedicated," Regina says carefully, her fingers tapping lightly on the podium next to her presentation on sustainable business practices. "Though perhaps we should stick to business questions?"
"It is a business question!" Henry grins, remembering how Aunt Ruby always says the best plans are the bold ones. "See, I'm doing this school project on successful women leaders, and you're literally perfect. My mom talks about you all the time. Well, your business strategies. And sometimes your suits. But mostly business!"
More laughter from the crowd. Regina's lips twitch as she glances at the security cameras - the ones Jake had promised wouldn't catch Henry's face clearly. "Perhaps we should continue this discussion after the lecture?"
"Really? That would be awesome!" Henry beams, already planning how to text Jake about his success. "My mom's gonna flip when she finds out. She has all your magazine covers. For research!"
Regina definitely looks amused now. "Indeed? And does this dedicated mother have a name?"
"Emma Swan!" Henry announces proudly. Then freezes, remembering this was supposed to be a stealth mission.
Regina's eyes widen slightly. "Emma Swan? The corporate investigator?"
"You know her?" Henry perks up, wondering if his mom's reputation in the business world is actually helping for once.
"By reputation." Regina's smile turns intriguing. "Why don't you wait for me after the lecture? We can discuss your... school project."
Twenty minutes later, Henry finds himself in Regina's temporary office, taking in the sleek modern furniture and the small apple tree sapling on her desk. He watches her pour two cups of apple juice. ("I assumed you're too young for cider.")
"So," Regina settles behind her desk, positioning herself with the same precise grace she used during the presentation, "you're Emma Swan's son."
"And you're her crush! I mean, her... professional interest?" Henry tries for innocent and fails spectacularly.
Regina chokes slightly on her juice. "I beg your pardon?"
"It's okay, she'll totally kill me later anyway." Henry pulls out his notebook, the one Aunt Ruby helped him prepare with "serious, business-like" questions. "But since I'm already busted, want to answer some questions? For my project?"
"You actually have a school assignment?"
"Of course! I may be sneaky, but I'm not a liar." Henry looks offended, straightening in the expensive office chair. "Mom raised me better than that. When she's not busy gushing over business magazines with you on the cover."
Regina's laugh is rich and warm, echoing in the pristine office. "You're quite something, Mr. Swan."
"Henry," he corrects, eyeing the wall of awards behind Regina's desk. "Mr. Swan makes me sound like a tiny businessman."
"Henry, then." Regina studies him thoughtfully, her fingers brushing against a framed photo of her apple orchard. "Does your mother know you're here?"
"Um... she thinks I'm studying at my friend Jake's house?" Henry tries his best innocent smile, the one that usually works on Aunt Ruby. "But in my defense, she's the one who won't admit she likes you!"
"And what leads you to believe she... holds such an opinion of me?"
"Besides the Google alerts? And the way she records all your TV appearances? And how she keeps finding excuses to investigate your company's competitors?" Henry counts off on his fingers, recalling all the times Aunt Ruby's caught his mom watching Regina's interviews. "Oh, and she has this thing about your scar being cute. But don't tell her I told you that."
Regina's hand drifts unconsciously to her lip. "I see."
"Plus, you're totally her type. Strong, scary-smart, probably good with kids..." Henry grins, glancing at the children's charity awards on display. "You like kids, right? Hypothetically?"
Regina Mills has never been fond of children. They are loud, unpredictable, and wholly unsuited to the structured, precise world she has built for herself. She excels in control—negotiations, legal strategy, boardroom warfare—not in the chaotic affections of childhood. And yet, Henry Swan is an anomaly. He is sharp, insufferably persistent, and entirely too perceptive for his age. He should irritate her—but he doesn’t. Instead, he lingers in her thoughts, challenging the certainty of her own indifference.
"I'm beginning to tolerate one in particular," she admits, eyes twinkling. "Though his subtlety needs work."
"Mom says subtlety is overrated." Henry flips open his notebook, the one Aunt Ruby helped him prepare. "Speaking of Mom, what's your opinion on bail bonds persons turned corporate investigators?"
"Getting a bit off topic, aren't we?"
"Nope! My assignment is about successful women and their personal lives too. Like, hypothetically, if someone's kid tried to set them up..."
"Henry..."
"Right, right. Professional questions first." He clears his throat, trying to sound like the business people outside. "What inspired you to become a CEO? Besides looking really good in power suits?"
Regina pinches the bridge of her nose, but she's smiling. "You are definitely Emma Swan's son." She doesn’t know where it comes from.
"Thanks! So, about those suits..."
"How about we stick to business questions, and then maybe discuss your mother's... professional interest?"
Henry's grin threatens to split his face. "Deal! But first - just between us - do you believe in love at first sight? Or should I tell Mom to keep pining dramatically?"
"I believe," Regina says carefully, her eyes drifting to the city skyline, "that some connections are inevitable."
"Cool." Henry scribbles in his notebook. "And how do you feel about hot chocolate? Asking for a friend. A very single friend who makes amazing hot chocolate..."
Regina laughs again, and Henry mentally high-fives himself. His mom is totally going to ground him until he's thirty, but the look on Regina's face? Worth it.
"One more question," he says innocently. "How do you feel about business dinners? Like, say, tomorrow night? I know this great Italian place..."
"Henry..."
"What? I'm just doing thorough research!" He bats his eyes. "For academic purposes."
"Of course." Regina shakes her head, but her smile remains. "Your mother must have her hands full."
"You have no idea." Henry pauses. "But she's worth it. The handful part, I mean. Just... you know, for your research."
Regina's expression softens. "I'll keep that in mind."
The door bursts open, and Emma Swan practically stumbles in, slightly out of breath and looking like she ran across campus. Her hair is wild, jacket askew, case files clutched under one arm and she freezes at the sight of Regina Mills sitting regally behind her desk.
Henry's eyes widen, though there's a hint of triumph in his expression that reminds Emma why she should never underestimate her kid.
"Did you really think I wouldn't have someone track down a worried mother?" Regina's smile is almost predatory, her fingers drumming lightly on the sleek desktop next to a small apple tree sapling.
"I... uh... hi?" Emma manages brilliantly, then spots Henry. "You are so grounded."
"Mom! Perfect timing! We were just talking about you!" Henry beams, completely unrepentant. "Did you know Regina thinks your investigation techniques are impressive?"
Emma's cheeks flush pink. "Henry..."
"And I was just telling her about how you record all her speeches-"
"Oh god."
"-and have a collection of that business magazines with her interviews-"
"Please stop talking."
"-and think her scar is really cu-"
"HENRY!"
Regina raises an eyebrow, watches this exchange with growing amusement, something tugging at her memory - candlelight, wine, a confession under stars... but that was just a dream, wasn't it? The kind she's been having more frequently since Emma Swan's name started appearing in her company's security reports.
"Miss Swan," Regina stands, circling her desk with predatory grace, heels clicking softly on the floor. "Your son is quite... resourceful."
"I am so sorry," Emma starts, then falters as Regina moves closer, nearly stumbling over her own feet. Papers from her hastily-grabbed case files threaten to spill. "He's not usually this..."
"Helpful?" Henry supplies cheerfully.
"...devious," Emma finishes, but her eyes are locked on Regina's face with an intensity that makes the air crackle. The sun through the office windows casts a warm glow that makes Regina look almost familiar, like something from a half-remembered dream.
"Actually, I'm always this helpful," Henry corrects, bouncing slightly in the expensive office chair. "Remember when I tried to set you up with that librarian?"
"Kid!"
"What? She was nice! Until we found out she collected ceramic clowns."
Regina's eyebrow arches, the gesture making Emma's heart do a funny little flip. "Ceramic clowns?"
"Hundreds of them," Henry shudders. "Mom ran so fast she left her favorite jacket behind."
"I did not run," Emma protests weakly. "I made a strategic retreat."
"Through the back door. During dinner."
Regina's laugh is rich and warm, sending shivers down Emma's spine. "I see bravery has its limits?"
"Hey, you haven't seen these clowns," Emma defends. "They had light-up eyes!"
"So, you prefer corporate raiders to clown collectors?" Regina's smile turns predatory, her perfectly tailored suit making Emma suddenly very aware of her own rumpled appearance. "How fascinating."
"I didn't... that's not... Henry, help?" Emma manages to drop half her files, papers scattering across the floor.
"Sorry Mom, you're on your own." Henry grins as Emma scrambles to gather them. "Besides, Regina was just telling me how intrigued she is by your work."
Emma's eyes snap to Regina, nearly bumping her head on the desk edge as she straightens. "She was?"
"I was discussing professional interest," Regina clarifies, though her eyes sparkle. "Your son seems determined to interpret things... creatively."
"I'm just stating facts!" Henry protests. "Like how Mom googled what kind of apples you grow in your orchard."
"HENRY!"
"You have an orchard?" Regina looks delighted, glancing at the small apple tree on her desk.
"No, you have an orchard," Henry corrects. "Mom just stalked- I mean, researched it. Thoroughly. Very thoroughly."
Emma looks like she's considering diving out the window, her face growing redder by the second. "I was... investigating agricultural investments?"
"Is that why you bookmarked all those apple pie recipes?"
"I'm going to sell you to the circus," Emma threatens, finally gathering her papers into a messy stack.
"Nah, you'd miss me." Henry turns to Regina. "She's actually a great cook. Especially breakfast. In case you were wondering. For professional reasons."
Regina leans against her desk, thoroughly entertained. "Does she always blush this much?"
"Only around beautiful women who intimidate her," Henry says helpfully. "Usually she's much smoother."
"Oh God," Emma groans and Regina feels that strange sense of Deja vu again - something about Emma's embarrassed smile seems so familiar, like a memory she can't quite grasp.
"Have we..." Regina starts.
"Met before?" Emma finishes softly, her own expression distant. "No, but... maybe in another life?"
The words echo strangely in Regina's mind, mixing with half-remembered dreams.
"I had a dream..." Regina murmurs, then catches herself. "That is, I mean..."
"About destiny?" Emma's voice is knowing, gentle, despite her awkward stance.
"About dinner," Regina finds herself saying. "In candlelight. You wore black..."
Emma's breath catches. "And you wore burgundy."
They stare at each other, the air heavy with possibility and something else, that tastes like magic and feels like fate.
"YES!" Henry pumps his fist. "I mean... how interesting. Professionally speaking."
"Henry," Emma warns, though she can't seem to look away from Regina.
"What? I'm just saying, if you both dreamed about having dinner together, maybe that's a sign you should... have dinner together?"
Regina's lips twitch. "Is your son always this subtle?"
"Like a brick through a window," Emma sighs. "I'm really sorry about all this. I had no idea he was planning to crash your lecture."
"To be fair, I did get some great material for my assignment," Henry points out. "And Regina got mom's private number, so really, everyone wins!"
"I... wait, what?"
Regina holds up her phone. "I may have had my assistant find your contact information. For... professional purposes, of course. "
"Professional reasons." Emma repeats faintly, fidgeting with her sleeve. “Maybe we could go to that little cafe near the park? You know, the one you... um... talked about last week?” She can feel her face heating up. “I figured, well, it’s kind of... nice, but not, like, too fancy? I mean, I didn’t want to, you know, overdo it.” Her voice trails off as she meets Regina’s eyes, a little unsure, but hoping her nervousness doesn’t show too much.
"Without teenage interference?" Regina smirks.
"HEY!"
"I'd... yeah," Emma manages, her smile brilliant despite her disheveled state.
"Excellent." Regina writes something on a business card. "Tomorrow night? Unless you need to run background checks on this cafe first?"
"That was one time!" Emma protests. "And in my defense, that sushi place you were at, did have three health code violations!"
"See?" Henry stage-whispers to Regina. "She really cares about your safety."
"Kid, I swear..."
"I must admit," Regina interrupts, "I find attention to details quite... appealing."
Emma's blush returns full force.
"Though perhaps less attractive than someone who keeps Google alerts for my press appearances?"
"I'm going to send you to boarding school," Emma tells Henry.
"Worth it!" He grins. "So, about that dinner..."
"Which you will not be attending," Emma says firmly.
"But-"
"No buts! You're already grounded until you're thirty."
"Can't ground me if you're too busy making heart eyes at Regina!"
"I do not make heart eyes!"
"Miss Swan," Regina cuts in smoothly, "you're utterly charming when flustered."
Emma's mouth opens and closes soundlessly.
"And you," Regina turns to Henry, "are either deviously brilliant or brilliantly devious."
"I prefer 'helpfully strategic,'" Henry says proudly.
"Indeed." Regina hands Emma the business card. "Tomorrow at eight? I promise no ceramic clowns."
"I... yes. Eight. Good." Emma somehow manages to form words despite Regina's proximity.
"Excellent." Regina's smile is positively wicked. "Wear something nice. I've heard you clean up well."
Emma's eyes widen at the echo of dream-words.
"And Henry?" Regina adds.
"Yeah?"
"Thank you for the... thorough interview. I suspect you'll get an A."
"Thanks!" Henry beams. "So, about the wedding-"
"OUT!" Emma grabs his arm. "We are leaving now!"
"But I haven't asked about her feelings on grandchildren yet!"
Emma practically drags him toward the door, pausing only briefly. "Tomorrow at eight?"
"I'm looking forward to it," Regina confirms softly.
As they leave, Henry's voice carries back: "See? True love is totally worth getting grounded for!"
"I'm donating you to science!"
"Love you too, Mom!"
Regina sits back at her desk, touching her lips where phantom memories of a dream-kiss linger. Outside her window, she watches Emma and Henry cross the campus, their playful bickering visible even from this height.
Something about them feels... inevitable.
Like destiny. Like coming home.
She looks at her phone, where Emma's number now resides, and smiles. Sometimes dreams do come true.
Even if they need a little help from meddling teenagers first.