Chapter 26 - Dylan and Olive ♡︎

Dylan's car hummed softly as it rolled down the quiet streets of town, the sun still hanging lazily in the late afternoon sky. Olive sat in the passenger seat, her hands folded in her lap, glancing out the window every so often to take in the passing scenery. She was nervous at first — her very first real date — but Dylan's easy smile and laid-back voice had started to calm her nerves a little. He wasn't nearly as intimidating as she thought he'd be.

They started the evening at the movie theater downtown, where the smell of popcorn filled the air and the chatter of students echoed from every corner. Dylan had let Olive pick the movie, which she'd done with a shy, uncertain look on her face, mumbling something about not wanting to choose wrong. He had just laughed and said, "Then we'll see both if we have to." That earned a small giggle from her — the kind of quiet, sweet laugh that made Dylan grin wider than he meant to.

During the movie, Olive sat stiffly at first, her hands gripping the edge of her seat as if she were afraid of doing something wrong. But as the story went on, she began to relax. Dylan had bought her a small popcorn, but somehow, she ended up with his too, because he kept offering it to her with a teasing smile. Every time their fingers brushed, she blushed.

When the credits rolled and they walked out into the fading daylight, Dylan said, "Okay, that was actually better than I expected. Guess I should let you pick more often."

Olive smiled bashfully, brushing a strand of hair behind her ear. "I just thought it looked cute," she said softly.

"It was," he agreed, though he wasn't talking about the movie.

Afterward, they drove to the bowling alley a few blocks away. The neon lights buzzed softly above them, and the sound of pins crashing and laughter filled the air. Olive hesitated at first, clutching the rental shoes awkwardly in her hands, but Dylan was patient. He helped her pick out a ball, joked about how seriously people took bowling, and even went first to show her how it was done.

When it was her turn, Olive lined up her shot, her tongue peeking out slightly in concentration as she swung the ball — and it immediately veered into the gutter. Dylan laughed good-naturedly, but not cruelly. "Alright, alright, bumpers it is," he said, grinning as he waved the attendant over.

Olive's cheeks turned pink. "I told you I was bad," she mumbled.

"Bad?" Dylan teased. "Nah, you're just giving the rest of us a chance."

By the second game, Olive was giggling more than she was actually bowling. Each time she hit a single pin, she celebrated as if she'd won a trophy, her soft laugh echoing over the lanes. Dylan found himself grinning every time she did — there was something ridiculously contagious about her joy, even over something as small as knocking over a few pins.

When they finally gave up after an hour of terrible bowling, they drove to a small ice cream shop near the edge of town. It was quiet, cozy, the kind of place with fairy lights strung around the windows and the faint smell of vanilla and waffle cones in the air. Olive picked strawberry, of course — the light pink color matched the blush that seemed permanently on her cheeks tonight — while Dylan went for mint chocolate chip.

They sat on a bench outside, the sky turning a soft shade of purple as the sun finally dipped below the horizon. Dylan leaned back casually, resting his arm along the back of the bench as he turned to look at her. "So," he said, "I guess I should tell you something about me, huh?"

Olive looked up from her ice cream and nodded shyly. "I mean... if you want to."

Dylan chuckled. "Well, I guess the main thing is, I'm the new quarterback for the team now — ever since Cole injured his leg last season. He's been coaching us and helping out, which is... kind of weird, honestly. He knows what he's doing, but, man, it's like every time I breathe wrong, he's there correcting me."

Olive blinked softly, listening.

Dylan sighed, rolling his shoulders a bit as if the thought alone annoyed him. "We've been butting heads for a long time. Even before I took over. Cole's always been the golden boy — the one everyone listens to, looks up to. He's good at it too, I'll give him that. The guys trust him. But it's hard, you know? Trying to fill in for someone like that. He's got history with the team, with the school... with pretty much everyone."

Olive hesitated, her fingers fidgeting with the edge of her cup. "He told me he used to play football," she said quietly.

"Yeah," Dylan nodded. "He was the best. Still kinda is, even if he's not on the field. He's the one who keeps us all in line. But between you and me..." he gave a crooked grin, "it's tough trying to live up to someone like Cole Walter. Especially when everyone keeps comparing us."

Olive smiled faintly, though something in her chest felt heavy. "That must be hard," she said softly.

Dylan shrugged, pretending it didn't bother him. "Eh, I'll manage. I'm not him, and that's fine. But sometimes it feels like he's still running the team through me."

Olive didn't know what to say to that. Her thoughts tangled quietly in her head, each one leading back to Cole — his voice, his teasing, the way he'd looked at her that night by the flower field. Every time Dylan mentioned his name, her heart beat faster, not with anger or loyalty but something confusing and fluttery.

She blinked quickly, trying to shake the thoughts away, but they clung stubbornly, making her cheeks warm.

Dylan noticed her silence and smiled softly. "Hey," he said, his voice gentler now. "I didn't mean to make things awkward. Forget I said anything."

Olive shook her head quickly. "No, no, it's okay. I just..." She trailed off, not sure what to say. How was she supposed to explain that every time someone mentioned Cole, her heart did something strange?

Dylan chuckled, brushing it off. "Well, let's not talk about him, then. Tonight's about you."

Olive smiled faintly and nodded, though a small part of her couldn't stop thinking about Cole anyway.___

After finishing their ice cream, Dylan tossed his napkin into the trash and turned to Olive with an easy smile. "You know," he said, nodding toward his car, "it's still early. Want to drive around for a bit? There's this road just outside of town that's quiet — you can see the lights from the hills. It's kind of my favorite spot."

Olive hesitated for a moment, her hands curling around her small purse. A soft breeze blew her hair against her cheek, and she tucked it behind her ear before answering. "Um... sure," she said shyly. "That sounds nice."

"Cool," Dylan said, flashing her a grin before walking ahead to open the passenger door for her. Olive blinked in surprise at the gesture but thanked him quietly, slipping into the seat and smoothing down her dress. The car ride started off with soft music playing through the speakers, something mellow and easy — a song she didn't recognize but liked anyway.

They drove past quiet neighborhoods, then out toward the edge of town where the roads became winding and open. The glow of streetlights faded behind them, replaced by the soft shimmer of stars beginning to appear in the twilight sky. Olive leaned her head slightly toward the window, watching the way the lights from distant houses flickered faintly across the horizon.

Dylan glanced at her from the corner of his eye. "You're quiet," he said after a while, not accusingly but with a teasing smile. "You always this shy, or just saving your words for special occasions?"

Olive blushed, laughing softly. "I'm... always like this," she admitted, her voice barely above the hum of the engine. "I guess I just... don't talk much unless I really know someone. I'm really shy — I've been that way my whole life."

Dylan nodded thoughtfully, one hand resting loosely on the steering wheel. "Yeah? Doesn't seem like a bad thing to me. You're calm. It's kinda nice. Everyone else around here's always trying to be loud or noticed."

Olive smiled faintly, looking down at her hands. "That's... what my parents said too," she murmured. "But they thought maybe it was too much. They wanted me to get out more, meet people, not be so scared of everything. That's why I moved in with the Walters."

Dylan raised an eyebrow. "Really? That was their idea?"

Olive nodded. "Yeah. My mom and Katherine are really close — they've been friends since forever. They thought living here, with Jackie and all the boys, might help me open up a little more."

Dylan chuckled under his breath. "Well, they weren't wrong about the 'meeting people' part. The Walter house is like a circus. You've got Jackie, who's practically the boss of everyone, and then Cole, who—" He stopped himself mid-sentence, glancing at her. "Sorry. Didn't mean to bring him up again."

Olive's lips curved in a small, nervous smile. "It's okay," she said softly. "You can talk about him. I don't mind."

Dylan nodded slowly and went quiet for a few moments, the sound of the tires against the road filling the silence. "So you and Jackie are close?" he asked finally.

Olive's face brightened a little. "Very close," she said warmly. "She's like my sister. We've known each other since we were kids — we used to have sleepovers and watch movies all the time. She's always been the brave one, the one who stands up for herself and for me too. I don't know what I'd do without her."

Dylan smiled at the way Olive's eyes softened when she talked about Jackie. "That's nice," he said. "It's good you've got someone like that. Jackie's... yeah, she's got a big personality, but she means well. And she definitely looks out for you."

"She really does," Olive said with a small laugh. "Sometimes a little too much. She tries to make me do things that I'd never have the courage to do on my own."

"Like tonight?" Dylan teased lightly, glancing at her.

Olive's cheeks turned pink. "Yeah... kind of," she admitted. "I didn't even know what to wear. Jackie picked everything — she even did my hair."

"Well, she's got good taste," Dylan said smoothly. "You look beautiful, by the way. I mean that."

Olive's face turned bright red. She looked away quickly, pretending to focus on the stars out the window. "Thank you," she whispered. "That's... really nice of you."

They drove in silence for a while after that, comfortable and quiet. The road stretched on ahead of them, lined by open fields and scattered trees swaying in the night breeze. Dylan finally pulled off onto a dirt path that led up to a small overlook. When he parked the car, Olive stared out the windshield in awe. From where they sat, the entire town spread out below them — little clusters of glowing lights twinkling in the dark, like fireflies scattered across the valley.

"Oh," Olive breathed softly, her eyes wide. "It's beautiful."

"Yeah," Dylan said, leaning back in his seat with a satisfied grin. "Told you it was worth the drive."

Olive nodded slowly, still staring out the window. "It's so peaceful," she said. "You can see everything from up here. It feels... quiet. Like the world finally stopped moving so fast."

Dylan looked at her instead of the view, his voice low and genuine. "Yeah. It really does."