Operation Boo BeginsTwo Weeks Before Halloween - Town Hall Office
Regina was never one to act without purpose, especially when it came to affairs of the heart. After all, her relationship with Emma had taught her the importance of patience—and strategy. So, after a few weeks of planning, Regina decided that Halloween, with its blend of mischief and warmth, would be the perfect night to ask Emma to marry her. The thrill of Emma's shock, paired with her own delight in catching her off-guard, had already brought a smile to her lips more than once.
As she sat at her desk, her fingers tapped thoughtfully against her planner. The key was keeping Emma completely unaware until the final moment, allowing her to believe that her ridiculous Halloween puns were working on Regina. Little would Emma know that she was merely playing her own role in a much larger plan.
Decisively, Regina picked up her phone and dialed a number. Ruby answered on the second ring. "Hey, Regina. What's up?"
"I need a bit of help, and it requires a certain amount of discretion," Regina replied smoothly, her tone measured yet warm.
"Oh, I'm intrigued," Ruby laughed, instantly sensing Regina's unusual excitement.
Coordinating with Friends - Granny's Secret Meeting
A few days later, Regina sat in a corner booth at Granny's, hidden from the rest of the patrons. Ruby, Henry, and Belle gathered around her, their faces alight with curiosity.
"So what's the big plan, Mom?" Henry asked, clearly excited. "You never set up a meeting like this unless it's serious."
"It is serious," Regina said, unable to hide the small, excited smile tugging at her lips. "I'm going to propose to Emma."
Henry's eyes widened, and he broke into a huge grin. "No way! That's amazing!"
Belle and Ruby shared delighted glances before leaning in, eager to hear more. "So… how are you going to do it?" Ruby asked, barely containing her excitement.
Regina outlined her idea, explaining how she wanted Emma to believe she had the upper hand, unaware of the surprise waiting for her that evening. "Emma has this idea that she can surprise me," Regina said with a hint of amusement.
She quickly laid out her plan, explaining how she wanted to wait until the evening of the Halloween party to propose, and how she needed to distract Emma throughout the day so she wouldn't suspect a thing. Ruby's eyes lit up as Regina spoke, clearly enjoying the idea of playing a part in such a scheme.
"So, basically, you want us to keep her busy?" Ruby said. "Make sure she doesn't catch on that you're up to something?"
"Precisely," Regina said, nodding. "I want her thinking she's the one trying to get a reaction out of me, not the other way around. If I know Emma, she's going to be persistent about her silly Halloween jokes. She'll spend all day trying to make me laugh, and I intend to let her think she's winning."
Henry was practically bouncing in his seat. "Oh, this is going to be amazing. I can't wait to see her face."
A Week Before Halloween - Coordinating with the Town
Over the following week, Regina subtly enlisted the help of a few trusted allies, ensuring each person knew their role without revealing too much. First, she had Henry plant the seeds, casually suggesting to Emma that she "get Regina into the Halloween spirit" with some playful, cheesy puns. As she anticipated, Emma took the bait enthusiastically, never suspecting that Henry's idea wasn't entirely his own.
Regina then met with Granny over tea to finalize the setup at the diner. "I need a quiet moment amid the party," she explained, stirring her cup thoughtfully. "A small lull, just enough for Emma and me to be alone—even if it's in front of everyone."
Granny's eyes twinkled as she gave a knowing smile. "Don't worry, sweetheart. I'll make sure the music dips just when you need it. Consider it done."
Belle, meanwhile, was tasked with overseeing the decorations, ensuring they struck the perfect balance of festive spookiness with a touch of elegance. Regina's instructions were precise. "It needs to blend in with the party's atmosphere," she explained, "but stand out enough to make it feel like the moment was there, waiting for us, all night."
Belle chuckled, eyes gleaming with a mix of amusement and admiration. "You really thought this through, haven't you?"
Regina's gaze softened, her voice lowering just slightly. "I have. I want her to know exactly what she means to me. And to see her expression when she realizes… it'll make every bit of planning worthwhile."
Halloween Morning - The Day of the Proposal
The moment Regina awoke, a small thrill of anticipation coursed through her. Today was finally here, and Operation Boo, as Ruby had dubbed it, was officially in motion. She received a text from Ruby confirming that everything was ready.
Throughout the day, she encountered Emma's ludicrous antics: a ghost costume left on her porch, an elaborate pumpkin display in front of her office, and even Emma herself appearing in increasingly silly costumes, each time trying to prompt a smile or laugh. Although it took considerable control, Regina maintained her cool composure, letting Emma believe she was unaffected by her silly attempts. But underneath her poised exterior, Regina felt a warmth growing with each of Emma's ridiculous gestures. If Emma only knew how much she enjoyed these small, earnest acts of affection.
Evening at Granny's Halloween Party - The Proposal
By the time the sun had set and the Halloween party was in full swing, everything was in place. Regina arrived at Granny's dressed to impress, her elegant red dress hugging her form, her hair styled in loose, soft waves. She knew the effect it would have on Emma; she had chosen this look specifically because she knew how it would make her heart skip a beat.
She spotted Belle right outside near the door, giving her a quick nod. "Is everything ready?" she asked quietly.
Belle grinned. "You're all set. The music will dip right at the end of the song you're dancing to, so you'll have your moment. Emma's been so busy trying to figure out why you're not cracking that she has no idea what's about to hit her."
Regina smirked. "Perfect." She glanced around, scanning the room for Emma. "And you're sure she doesn't suspect anything?"
"Oh, she's clueless," Belle said, barely stifling a laugh. "She's been sulking about it all evening, trying to figure out how to break you, and it's driving her nuts. She's even convinced she's losing her touch."
Regina's gaze shifted to where Emma sat at the bar, distracted and apparently moping. "Thank you, Belle," she replied softly. "Now, it's my turn."
Back to the Dance Floor - The Proposal
As Regina made her way over to the bar, she couldn't help but feel a rush of exhilaration. This was it. All the planning, all the secrecy, it was about to pay off. And when she saw Emma's face, that perfect blend of surprise, confusion, and love, she knew it had all been worth it.
She slipped into her role effortlessly, teasing Emma, seducing her with subtle glances and suggestive touches, all the while knowing exactly how this would end. When she finally conjured the rose, the look on Emma's face was everything—adorably flustered, and utterly captivated.
As the two fell into a rhythm, swaying gently to the music, several moments later, Regina rested her hands on Emma's waist, keeping her movements subtle but drawing Emma in close.
And as she got down on one knee, hearing the delighted gasps from around the room, she felt a warmth and calm settle over her. She had planned every detail, but the way Emma's eyes softened was something she couldn't have prepared for. It was perfect.
Emma's stunned, stammering response—along with her prolonged, bewildered silence—only made the moment sweeter. And when she finally said yes, Regina felt a wave of relief and joy crash over her, one that she hadn't even realized she was holding back.
As they danced together, surrounded by the cheers and laughter of their friends, Regina allowed herself to relax, knowing that everything had gone exactly as she had hoped. Emma had been caught off-guard, everyone had played their parts, and now, they were starting their forever.
For Regina, it was more than just a proposal—it was the culmination of everything she had fought for, everything she had come to cherish. And now, as she looked into Emma's eyes, she knew with absolute certainty that this was just the beginning of their greatest adventure yet.
