Chapter 25 - Olive's Date ♡︎

The morning sunlight filtered softly through the curtains of Olive's room, painting the walls in a golden hue. Olive stirred quietly beneath her blanket, blinking a few times before stretching her arms above her head with a small yawn. Her bunny-patterned pajamas hung loosely on her, adding to her childlike appearance as she rubbed the sleep from her eyes. The house was already alive with faint noises—voices, footsteps, and the smell of breakfast wafting from the kitchen.

She shuffled out of bed, still groggy, and made her way toward the door. Her hair was a bit messy, falling in soft waves around her face. She grabbed her toothbrush and stepped into the hallway, only to freeze when she nearly walked straight into Cole. He was leaning casually against the wall near her door, arms crossed, his green eyes catching hers instantly.

"Good morning, tiny," he said with that infuriatingly confident smirk tugging at his lips. His voice was smooth and teasing, but there was something underneath it—something a little more intent, a little more watchful.

Olive blinked up at him, startled, clutching her toothbrush to her chest. "G-Good morning," she replied softly, her voice small and uncertain. Her cheeks flushed slightly as she realized he was staring at her, clearly amused by her flustered state. She tucked a strand of hair behind her ear, then stepped around him carefully to head toward the bathroom.

As she started walking down the hall, she could hear his footsteps behind her. She turned her head slightly, frowning in confusion. "Why are you following me?" she asked quietly, her tone shy but suspicious.

Cole tilted his head like it was the most innocent question in the world. "What? I'm not following you," he said, his tone feigning surprise. "Just happen to be walking the same way." He shrugged, stuffing his hands into the pockets of his sweatpants, his smirk never fading.

Olive glanced at him again, narrowing her eyes a little. "You're acting weird," she mumbled softly, though her voice lacked any real bite.

Cole chuckled under his breath. "And you're always accusing me of things I'm not doing."

Olive didn't respond, just rolled her eyes gently and turned away, her footsteps light against the wooden floor. She was too tired to argue, too shy to push further. But Cole's gaze followed her, his smirk fading into something more serious. He wasn't going to let her go on that date—not today, not with Dylan. There was no way he'd allow it.

Just as Olive reached the bathroom door and was about to go inside, a familiar voice echoed from behind them. "Cole!" Jackie's tone was sharp, cutting through the quiet morning like a blade.

Cole froze, his shoulders stiffening slightly as Jackie appeared at the end of the hall, hands on her hips and eyebrows raised. Her expression said everything—she knew exactly what he was up to.

"Stop following Olive around," Jackie said firmly, walking toward them. "She can't even go to the bathroom without you hovering over her? Seriously?"

Cole sighed, trying to play it off. "I'm not hovering. I was just—"

"Don't even start," Jackie interrupted, crossing her arms. "You're acting like a guard dog, and it's weird. Olive has a big day ahead of her. Leave her alone."

Olive stood awkwardly between them, clutching the bathroom door handle, her cheeks pink with embarrassment. She glanced nervously between Jackie and Cole, wishing she could just disappear.

Cole exhaled through his nose, glancing at Olive, then back at Jackie. "I'm not doing anything wrong," he muttered, his voice low but defensive.

Jackie gave him a knowing look. "You're doing something, Cole. Don't pretend you're not." She stepped closer, lowering her voice so Olive wouldn't overhear too much. "You need to let her live a little, okay? You can't control everything."

Cole clenched his jaw but didn't answer. Jackie lingered for a moment longer, then gave Olive a soft smile. "Go get ready, Ollie," she said warmly. "We've got a big day to prepare for."

Olive nodded, smiling faintly, before slipping into the bathroom and quietly closing the door behind her.

The hallway went silent for a beat. Cole stood there, hands tightening into fists in his pockets, his expression unreadable. Jackie sighed and gave him one last look before turning away.___

Jackie's room was warm and bright, sunlight spilling through the white curtains and landing softly on the piles of clothes scattered across her bed. Dresses of every color and style lay neatly folded, each one a potential outfit for Olive's big day. Jackie stood with her hands on her hips, her expression a mix of excitement and focus, while Olive sat shyly on the edge of the bed, her hands twisted nervously in her lap.

"Okay," Jackie said, pulling out a soft pink dress with little floral embroidery along the hem, "this one is simple but adorable. Totally your style."

Olive's cheeks turned a gentle pink as she looked at it. "It's really pretty," she said quietly, her voice almost a whisper. "But... maybe it's too much? What if it's too fancy for a first date?"

Jackie chuckled, shaking her head as she laid the dress over Olive's legs. "Olive, you could wear a paper bag and Dylan would still think you're adorable. Trust me, this is perfect. It's sweet, not over the top."

Olive giggled shyly, brushing her fingers along the soft fabric. "You really think so?"

"I know so," Jackie said with a grin. "And we'll pair it with those white flats we found in the closet yesterday. You'll look amazing." She moved to her dresser and pulled out a few accessories—simple gold earrings and a small bracelet that shimmered in the light. "Something delicate, just like you."

Olive smiled softly at the compliment, her heart fluttering a little. She always admired how confident Jackie was, how easily she could make her feel special. Jackie started brushing Olive's hair, the strokes gentle and rhythmic. The atmosphere in the room was cozy and calm, filled with the faint hum of music coming from Jackie's speaker.

Meanwhile, just outside the door, Cole stood with his back against the wall, trying—and failing—to look casual. His green eyes darted toward the door every few seconds, his expression tight with curiosity. He could hear faint murmurs of Jackie and Olive's voices but couldn't make out what they were saying.

He leaned in just a little closer, tilting his head. Maybe he'd catch a word or two if he was quiet enough.

"Pink dress," he muttered under his breath when he thought he heard the word. His brow furrowed slightly. "No way she's wearing that for him."

Just as he leaned a little closer to the door, a voice suddenly broke the quiet hallway. "Dude. What are you doing?"

Cole flinched and spun around, his heart skipping a beat. Standing a few feet away were Alex, Isaac, and Nathan—all three of them looking equal parts amused and confused. Alex crossed his arms, a knowing smirk playing on his face.

"Are you—" Isaac started, raising an eyebrow, "—listening at the door?"

Cole straightened immediately, his expression hardening into mock offense. "No," he said quickly, his tone defensive. "Of course not."

Nathan snorted, trying to hold back a laugh. "Oh, yeah? Because it totally looks like you're eavesdropping on your little sister's date prep."

"She's not my sister," Cole snapped automatically, then immediately regretted how fast he said it. The three boys exchanged looks and burst out laughing.

Alex leaned against the opposite wall, smirking. "You've officially lost it, man. Eavesdropping? Really? What's next—hiding in the bushes to make sure Dylan opens the car door for her?"

Cole groaned, dragging a hand down his face. "You guys are ridiculous. I was just—just making sure she's okay. That's all."

Isaac chuckled, nudging Nathan. "Right, right. Because she's definitely in danger of being over-accessorized."

Even Nathan cracked up at that one, and Cole glared at both of them. "You're hilarious," he muttered. "I just don't think Jackie should be letting her—"

Alex cut him off, still grinning. "You mean, you don't think Olive should be going on a date with anyone who's not you."

Cole froze for a second, caught off guard by how easily Alex had hit the nail on the head. "That's not—" he started, then sighed heavily. "You guys don't get it."

"Oh, we get it," Nathan said, raising his brows. "You've gone soft, man. Never thought I'd see Cole Walter eavesdropping outside a girl's room like he's in some cheesy movie."

Cole rolled his eyes but didn't argue this time. Instead, he looked back toward the door, a quiet frustration flickering across his face. Inside, he could still hear Olive's laugh—a soft, sweet sound that only made his chest tighten more.

Alex noticed it too and placed a hand on his shoulder. "Just let her have her moment, Cole. You'll drive yourself crazy trying to control everything."

Cole didn't answer, but his jaw clenched. He knew Alex was right—he just couldn't admit it out loud. Because the truth was, it wasn't about control. It was about the ache in his chest every time he thought about Olive smiling at someone else.

Behind the door, Jackie and Olive were laughing again. Cole sighed and stepped back, muttering under his breath, "I'm not eavesdropping."

The sound of soft footsteps echoed down the hallway as Olive and Jackie emerged from the bedroom. Jackie walked with a proud little smile on her face, her arm looped through Olive's as if she were escorting royalty. And in some ways, that's exactly how Olive looked—royal in her own shy, delicate way. She wore the soft pink dress Jackie had picked, the one that brought out the faint blush in her cheeks and made her look like something out of a dream. Her hair was curled loosely and fell over her shoulders like waves of silk, and the little gold bracelet Jackie had lent her shimmered faintly as she nervously fidgeted with it.

Jackie whispered something to her as they approached the stairs, and Olive giggled quietly, though the sound carried easily through the living room below. Katherine was the first to look up, and her expression immediately softened into a warm, proud smile. George followed her gaze, his face lighting up in quiet approval as he nudged his wife.

"Oh, sweetheart," Katherine said softly as Olive reached the bottom of the stairs, "you look absolutely beautiful."

Olive's face went red instantly, her hands twisting nervously at her sides. "Thank you," she said shyly, her voice almost lost in the living room chatter. Jackie gave her a little encouraging nudge, grinning from ear to ear.

"She does, doesn't she?" Jackie said proudly. "You should've seen how nervous she was about wearing that dress—took me ten minutes to convince her."

Katherine laughed, her eyes full of fondness. "Well, I'm glad you did. Dylan won't know what hit him."

Olive covered her face with her hands, embarrassed, but couldn't help giggling a little. "Please don't say that," she mumbled through her fingers, though she secretly appreciated the compliment.

George chuckled as he adjusted his glasses. "I have to agree, Olive. You look lovely, really. You'll knock him off his feet."

"George!" Katherine said playfully, nudging him. "Don't make her more nervous than she already is."

Olive peeked out from behind her hands, her cheeks still pink, but there was a small, timid smile tugging at her lips. Jackie squeezed her shoulder gently, proud of her best friend for stepping so far out of her comfort zone.

Then came the sound of heavy footsteps from the hallway. Cole walked in from the kitchen, his hair still slightly messy and his green eyes sharp as ever. The moment his gaze landed on Olive, he froze mid-step. For a brief second, he looked completely caught off guard—like he'd forgotten how to breathe.

Olive, feeling his stare, looked up at him timidly. "H-Hi, Cole," she said softly.

He didn't answer right away. His eyes flickered over her pink dress, the soft curls in her hair, the faint shimmer on her wrist. She looked... unreal. Too innocent. Too delicate. Too perfect. And the fact that she was dressed like that for someone else made his jaw clench.

"You look..." he started, his voice quieter than usual. He cleared his throat and forced a neutral expression. "You look nice."

Olive's shy smile widened just a little. "Thank you," she said softly, her voice barely above a whisper.

Katherine clasped her hands together and said, "Well, Dylan should be here any minute! Why don't we all take a few pictures before she goes?"

Jackie immediately pulled Olive toward the living room, positioning her near the fireplace while Katherine went to grab her phone. Olive stood stiffly, unsure what to do with her hands, and Jackie laughed and fixed a strand of her hair.

"Relax," Jackie whispered teasingly. "You're doing great. It's just a picture."

Olive giggled nervously, her fingers brushing at her skirt. "I know, I just... I don't know what to do."

"Smile," Jackie said simply. "And don't trip if he brings you flowers."

That made Olive laugh, and right as the sound left her mouth, Katherine snapped the picture. "Perfect!" she said cheerfully. "Oh, you two look adorable."

George nodded in agreement, his eyes twinkling. "I think we've got ourselves a perfect memory here."

While everyone smiled and fussed over Olive, Cole stood silently in the corner, leaning against the wall with his arms crossed. His jaw was tight, his green eyes dark with something that wasn't easy to read—something simmering just beneath the surface.

Isaac, who had wandered in halfway through the commotion, leaned over and whispered, "You okay there, Cole? You look like you're about to bite someone."

Cole didn't look at him. "I'm fine."

"Uh-huh," Isaac said, unconvinced. "You sure? Because you've got that look again—the one you had when Jackie told you she was seeing Alex."

Cole shot him a glare, and Isaac held up his hands in surrender, chuckling. "Alright, alright. I'm just saying."

Then the sound of a car engine pulling up outside made everyone pause. Katherine peeked out the window and smiled. "That must be Dylan."

Olive froze instantly, her stomach flipping. "Oh no," she whispered under her breath, clutching her purse a little tighter. Jackie placed a reassuring hand on her back.

"Hey," she said softly, "you've got this. Just be yourself, okay? And remember—no pressure. If you don't like him that way, it's okay too."

Olive nodded, her heart fluttering nervously. Katherine opened the door, and sure enough, Dylan stood there with his charming grin and a small bouquet of flowers in hand.

He smiled wide when he saw Olive. "Wow," he said, almost breathless. "You look incredible."

Olive's face turned red again as she took the flowers. "Thank you," she murmured, tucking a strand of hair behind her ear.

As Dylan greeted everyone, Cole's eyes darkened. His arms crossed tighter, and his jaw flexed hard enough to make it ache. Jackie noticed it immediately and gave him a warning look, silently telling him not to ruin this.

But Cole couldn't stop the wave of jealousy rising in his chest as he watched Dylan offer his arm to Olive. She hesitated for a moment, looked back at Cole with uncertain eyes, and then took Dylan's arm anyway.

Jackie smiled proudly. Katherine looked like a proud mom. George beamed. But Cole—he stood there, silent and fuming, his green eyes following them until they disappeared out the front door.

Isaac muttered under his breath with a smirk, "Yup. He's doomed."

Cole didn't say a word. He just stared at the door, wishing it hadn't closed behind her.