Olivia sighed, gripping her suitcase handle tighter as she stepped out of the rideshare and onto the wet pavement outside her apartment complex. The sight of restoration trucks, industrial fans humming in the lobby, and the faint scent of damp drywall confirmed what she already knew—this was going to be a nightmare.
She barely took two steps inside before Mike, her landlord, spotted her.
"Olivia!" he called, waving her over. Dressed in a polo and khakis, his expression was both relieved and regretful.
"Hey, Mike," she greeted, trying to keep her voice even. "Just got back. What's the damage?"
Mike exhaled, rubbing the back of his head. "I won't lie—it's bad. The leak started in one of the penthouses, and the top floors got the worst of it. Your unit isn't a total loss, but there's water damage. The power's shut off in some areas, and we need to replace drywall, flooring, and check the wiring. We're estimating six weeks for repairs."
Six weeks.
Olivia swallowed hard and nodded, already mentally calculating her next steps. Crashing with someone wasn't her style, and the idea of sitting in a hotel for that long, staring at a broken apartment, made her restless.
Her home—a sleek, two-bedroom high-rise with floor-to-ceiling windows overlooking the Chicago skyline—was now a disaster zone. Water had seeped into the plush rugs, stained the walls, and ruined some of her books and framed travel photos. The kitchen ceiling had been cut open, exposing pipes and insulation. The place that had always felt so uniquely hers now smelled of wet drywall and cleaning chemicals.
There was nothing she could do about it now.
Her phone buzzed in her hand, pulling her out of her thoughts. Exhausted from her eight-hour flight from Hawaii, she barely had the energy to check it. But when she did, her brows furrowed at the unknown number flashing on her screen.
Unknown Number: One kiss from you is not enough.
Her cheeks warmed despite the fatigue weighing on her limbs. A smirk tugged at her lips as she quickly typed a response.
Olivia: Sounds like a personal problem.
Satisfied with her quirky comeback, she tucked her phone away and focused on the immediate issue—finding a temporary place to stay. She could do nothing more in the building at this hour, so she rolled her suitcase toward one of Chicago's downtown hotels and booked a room for the week.
Once inside, she wasted no time. A hot shower washed away the stiffness from the long flight, and by the time room service arrived with a fresh breakfast, she finally started feeling like herself again—recharged, ready to take on the world.
Settling onto the plush hotel bed, she opened her laptop and got to work. Emails, insurance claims, repair schedules—she had a long list of things to sort through. But one way or another, she would regain control over the chaos around her.
At some point, exhaustion won. When Olivia woke up, it was mid-afternoon. She blinked at the many missed calls and messages on her phone, groaning as she scrolled through them. Prioritizing business first, she called a local moving company to schedule them to move her belongings to a temporary storage facility. Next, she arranged for carpet cleaners to salvage what they could of her rugs. The books, however—those were a loss. Some had been with her since childhood, others were collector's items. That stung the most.
She still needed to go back and sort through what else she could salvage herself.
Shifting gears, she focused on work. Emails, prescription refills, and catching up on anything she might have missed while in Hawaii. She'd worked while there, but Emma's shenanigans had made it nearly impossible to focus sometimes.
That thought made her glance at the group chat, and she chuckled at the chaos. Photos of Emma and the girls on karaoke night, some blurry videos, and a hilarious shot of Daniel and another guy carrying Haley. It could have been one of the other sorority sisters' dates, but either way, it was a mess.
There were also texts from Haley and Emma checking in on her.
To Emma, she typed: Congratulations on your wedding! Don't worry about me today. I love you.
To Haley, she sent a more honest reply: It's a fucking disaster. Don't tell Emma—I told her everything's fine. You know how she gets. Have fun, drink for me. I'll tell you more when I visit next weekend.
With that, she set her phone aside, stretched, and exhaled. There was still so much to do, but at least she was moving forward.
By evening, Olivia found herself downstairs at the hotel bar, picking at her dinner while scrolling through her phone. The dim lighting, soft hum of conversation, and clinking of glasses created a cozy atmosphere, but her mind was elsewhere.
Her phone buzzed, pulling her attention away from the barely touched plate in front of her. She glanced down, expecting another message from Haley or Emma. Instead, the unknown number had responded.
Unknown Number: Are you sure about that? Because I don't think one kiss would be enough for you either.
She blinked, her fork pausing midway to her mouth. A slow heat crept up her neck. She knew exactly who this was—she just hadn't programmed his number into her phone yet.
Olivia set her fork down, staring at the message. Of course, he would say something like that. Before she could stop herself, she typed back.
Olivia: Confident, aren't you? Should I be flattered or concerned?
She hit send and took a sip of her drink, eyes flicking up to scan the bar. No one seemed out of place. No one watching her too closely. Still, the feeling of being observed lingered.
Her phone buzzed again.
Grayson: Maybe both.
Olivia narrowed her eyes at her screen, her fingers hovering over the keyboard. Are you following me?
Grayson: Maybe it's fate that we met again.
She scoffed, sending back a rolling eyes emoji, followed by, LOL.
Grayson: I can make dreams into reality.
Her brow arched as she typed, Olivia: What dreams?
There was a pause. Then, the familiar typing bubbles appeared. She watched them flicker for a few moments, waiting. Finally, his next message appeared.
Grayson: Well…
More typing bubbles.
Grayson: Then The lines blur when it comes to you.
She rolled her eyes but couldn't hide the small smirk playing on her lips. Big words for someone who hasn't tested that theory.
The response came almost immediately. Who says I haven't?
Olivia let out a short laugh, shaking her head as she typed back. Olivia: Pretty sure I'd remember. Unless you're counting in your dreams.
She bit her lip, debating how to respond. Instead, she reached for her wine and took a slow sip, letting the warmth spread through her before finally typing, Olivia: You always this smooth, or do I bring out the best in you?
A pause. Grayson: You? You make me reckless.
Olivia's fingers hovered over the keyboard, her heartbeat picking up just a little. Olivia: Dangerous words.
Grayson: Only if you're afraid of a little risk.
She smirked, twirling the stem of her wine glass between her fingers. Olivia: I don't mind risk. Just prefer knowing what I'm getting into.
Grayson: And if I said it's worth it?
She hesitated, staring at the screen. The playful banter had turned into something else—something heavier, charged.
Olivia: Then I'd say you're awfully confident for someone still trying to convince me.
Another pause. The typing bubbles reappeared.
Grayson: I don't have to convince you. You're already thinking about it.
Olivia let out a soft breath, biting the inside of her cheek. He wasn't wrong.
She leaned back in her chair, the soft glow of the bar lights making the ice in her drink shimmer. The tension between them, even through a screen, was undeniable.
Grayson: Enjoy your night, Olivia. Don't think too hard.
Her lips parted slightly as she read the message. He was the one who started this, yet he was the one ending it?
She let out a quiet laugh, shaking her head. Olivia: Tease.
A final message appeared before the typing bubbles disappeared.
Grayson: Only if you're impatient.
The next morning, Olivia woke to the sound of soft rain tapping against the hotel window. It was the kind of dreary morning that usually made her want to curl back under the covers, but today, she had plans—plans that had nothing to do with unpacking the chaos of her flooded apartment.
She stretched before rolling out of bed, her mind already set on her next mission: finding a new bookshelf. Some people turned to retail therapy in the form of clothes or shoes, but for Olivia, there was something therapeutic about wandering through old antique shops, searching for the perfect piece of furniture that had its own history. A bookshelf, especially, was more than just storage; it was a home for stories, a place to display the pieces of her that had survived all her moves, all her changes.
But first—coffee.
She slipped into a pair of ankle boots, threw on her trench coat, and grabbed her tote before stepping out into the crisp Chicago air. The rain had lightened to a mist, just enough to make the streets glisten. She took her time walking, savoring the rare moment of quiet in the usually bustling city, until she reached a small bistro she had visited a handful of times before. It was tucked between a boutique flower shop and a bookstore, its large windows fogged up from the warmth inside.
The scent of fresh espresso and baked pastries wrapped around her the moment she pushed through the door. Soft jazz played in the background, blending with the low hum of conversation. She made her way to the counter, ordering a cappuccino and a croissant before settling into a cozy corner near the window.
Her laptop opened with a familiar click, and soon, she was immersed in work—sifting through emails, checking prescription refill requests, and organizing her notes for the week ahead. The steady flow of people coming and going, the occasional scrape of a chair, the rhythmic clatter of cups being stacked—it was the kind of ambient noise that made her feel productive rather than overwhelmed.
By the time she finished her second cup of coffee, she had made a decent dent in her to-do list. Satisfied, she packed up and pulled out her phone, opening a map to check for nearby antique shops. There were a few she had visited before, but one caught her attention—Harrison & Co. Antiques, a shop she had been meaning to check out for months but never had the time. It was a bit of a walk, but she didn't mind.
Olivia tucked her laptop away, slung her tote over her shoulder, and stepped back into the misty morning air. The city moved at its usual pace around her, cabs splashing through puddles, pedestrians dodging each other with umbrellas in hand. As she strolled toward the antique shop, she let herself enjoy the moment—the smell of rain on the pavement, the promise of a good find waiting for her, and the quiet excitement of a day that was completely her own.
She was about to step inside Harrison & Co. when her phone buzzed in her pocket. Pulling it out, she glanced at the screen and saw Haley's name flashing across it.
Haley: How bad is it really? And don't lie to me like you did with Emma.
Olivia sighed, shaking her head as she typed back.
Olivia: It's a mess, but I'm dealing with it. Just taking a break before diving back into the chaos.
Haley: Where are you now?
Olivia: Grabbing coffee and then doing some antique shopping. Need a new bookshelf.
Haley: Of course you do. You and your bookshelves. Call me later, okay?
Olivia: Will do. Now go back to Daniel and being lovey-dovey.
She tucked her phone away, finally stepping inside the antique shop. The scent of aged wood, leather-bound books, and a hint of vanilla greeted her. The shop was dimly lit, the kind of place that invited slow browsing and hidden treasures. Shelves lined the walls, stacked with old novels, delicate porcelain, and trinkets from decades past. The wooden floor creaked softly beneath her boots as she wandered further in, trailing her fingers along the polished edges of a mahogany desk and pausing at an intricately carved cabinet that looked like it had stories of its own.
After scanning the room, her eyes landed on a bookshelf tucked near the back—a sturdy oak piece with detailed molding along the top. It wasn't overly ornate, but it had a charm to it, the kind of craftsmanship that felt rare in modern furniture. She ran her hand along the surface, inspecting the wood, already envisioning where it would go in her apartment once the repairs were done.
She finalized her purchases, including a vintage tournament dartboard, and left the antique shop feeling accomplished. But her day wasn't over yet.
Next on her list was a trip to Half Price Books. Stepping inside, she inhaled the familiar scent of well-loved paper and ink, feeling instantly at home among the cluttered aisles of books. She browsed slowly, trailing her fingers along the spines, pulling out titles at random. Some were familiar favorites, others unexpected finds she couldn't resist adding to her growing collection.
By the time she reached the checkout counter, she had a small stack—some classic literature, a couple of mysteries, and a travel book that caught her eye at the last second. The cashier, a young guy with thick glasses and a knowing smile, chuckled as he rang her up. "Stocking up?"
"Something like that," she replied with a grin. "I lost some of my collection in an apartment flood. Just trying to rebuild."
"That's rough," he said, handing her the bag. "But at least you get to go on another book hunt, right?"
"Exactly," Olivia agreed before heading back out into the rain.
Her last stop of the day was the rug restoration shop. She had called ahead and set up an appointment to bring in a few of her damaged antique rugs, hoping to salvage them. The shop, tucked into a quiet street corner, was a hidden gem—one she had discovered years ago when she first started collecting vintage home decor.
A bell jingled as she stepped inside, the scent of aged fabric and specialty cleaning solutions filling the air. A kind-faced woman greeted her at the counter. "You must be Olivia."
"That's me," she confirmed, rolling up the first rug carefully. "I had a little water damage issue, and I'm hoping you can work some magic."
The woman unrolled the rug across the inspection table, running her fingers over the fibers with a trained eye. "It's not the worst I've seen," she assured Olivia. "We can definitely restore this—some minor discoloration, but structurally, it's still intact."
Olivia exhaled, relieved. "That's good to hear."
They went through the rest of the rugs, assessing the damage and discussing the restoration process. By the time she left, she felt lighter, knowing at least some pieces of her home could be saved.
Back in her hotel room, Olivia settled onto the bed with a takeout lunch spread in front of her. She had changed into a pair of fitted jeans and a soft hunter-green cashmere sweater, comfortable yet polished. The hotel room, though temporary, looked lived-in but still organized—her suitcase neatly tucked in the corner, a small pile of books from her latest haul stacked on the desk, and her laptop open next to a notepad filled with scribbled to-do lists. Between bites of her sandwich, she juggled responding to emails, checking on apartment listings, and sorting through work files. Her phone buzzed with two new messages—one from Haley and one from Grayson. She smiled at Haley's name before pausing at Grayson's.
She opened Haley's message first. She wasn't going to let herself fall into the same trap again—answering every text, picking up every call, acting like some eager, wide-eyed puppy waiting for scraps of attention. That was exactly what had happened with Asshat, and she had no intention of repeating that mistake. This was the same pattern she had followed with Asshat, and she refused to let it happen again. No, she would take precautions. The sensation of excitement was just because she had been a little lonely—seeing all the couples at the wedding hadn't helped. But what had she been thinking when she kissed him? Was it just the rush of anticipation, the idea that she might never see him again?
She wasn't the type to bet on her heart—she bet on races, games, numbers, things she could predict. Love was never something she left to chance.
Her phone buzzed again, jolting her out of her thoughts. She glanced back at Haley's message, grateful for the distraction.
Olivia stared at the screen, her fingers drumming lightly against the edge of her phone. A week in Boston. It wasn't a bad idea. Haley was right—she could use the break. It wasn't like she had much keeping her in Chicago at the moment, aside from work and whatever emotional baggage she was avoiding unpacking.
She sighed and typed back.
Olivia: I don't know, Hales. Feels like running away.
Haley: It's not running away. It's a reset. Big difference.
Olivia: Debatable.
Haley: It's ONE week. Fresh air, good food, quality time with me. Come on. Say yes.
Olivia set the phone down and leaned back against the pillows, closing her eyes for a second. Boston meant a change of scenery, but it also meant time to think, which could be dangerous.
Her phone buzzed again.
Haley: I'll even take you to that speakeasy you liked last time.
A small smile tugged at Olivia's lips. Haley really knew how to sweeten a deal.
Olivia: Ugh, fine. You win.
Haley: I always do.
Olivia: I'll check flights later.
Haley: Check them now.
Olivia: Stop micromanaging my life.
Haley: I WILL if you book the flight.
Olivia huffed, shaking her head, but she couldn't help the smirk tugging at her lips.
Olivia: You're relentless.
Haley: And you love me for it.
Olivia: That's still up for debate.
Haley: Lies. You'd be lost without me. Also, you'd have zero plans outside of work and takeout.
Olivia: Excuse me, I also have Netflix and wine.
Haley: Wow, such a vibrant social life. Truly thriving.
Olivia: Some of us enjoy peace and quiet. Not everyone lives in a Hallmark movie like you do now.
Haley: Oh, please. If my life were a Hallmark movie, I'd have a quirky small-town job, an adorable golden retriever, and an ex-boyfriend who just came back from the big city to win me over. Instead, I have a mountain of moving boxes and Daniel's deep, slightly concerning passion for alphabetizing the spice rack.
Olivia: Right, because nothing says romance like an aggressively well-organized pantry.
Haley: It's honestly terrifying. I caught him REARRANGING the labels last night because he thought 'paprika should have more space to breathe.'
Olivia: That's it. I'm coming to Boston solely to stage an intervention.
Haley: YES. See? Now you have a purpose.
Olivia: Fine. But if I get there and you two are doing some weird couple-y cooking thing where you both reach for the same ingredient and stare into each other's eyes, I'm walking out.
Haley: That's fair. I'll make sure we do all our romantic staring before you arrive.
Olivia: Appreciate it.
Haley: Anything for my best friend. Now book the flight before I do it for you.
The next morning, Olivia woke to the sound of her hotel room's heating system kicking on, a steady hum filling the otherwise quiet space. The rain had finally stopped, leaving behind a dull gray sky outside her window. She stretched, groaning slightly, before reaching for her phone on the nightstand. A few notifications blinked on the screen—emails, a weather update, and, of course, a text from Haley.
Haley: Did you look at flights yet? Or are you still pretending Boston isn't a good excuse to come see your best friend?
Olivia smirked, rubbing the sleep from her eyes as she typed back.
Olivia: I haven't not looked.
Haley: That means no.
Olivia: It means I'm considering.
Haley: Book the damn flight, Olivia. You need this.
Olivia sighed and set her phone down. It wasn't like traveling was a big deal for her—she always did it. But this wasn't just a trip; it was a shift, a small escape. Not from anything in particular, just an excuse to spend time with Haley and shake up her routine. But what was left for her to do in Chicago? Wait for updates on her apartment. Work from a hotel room indefinitely?
With that thought, she swung her legs over the side of the bed and stood up, grabbing her laptop. If she was going to consider it, she might as well see what flights were available. But first—coffee.
A short while later, she sat in the hotel café, a fresh cup in front of her and her laptop open. She scrolled through flights to Boston, clicking in and out of different options. A direct flight tomorrow evening. Reasonable price. No layovers. It was almost too easy.
Her phone vibrated again. Another message. This time, not from Haley.
Grayson.
She stared at his name, her finger hovering over the notification. This time, she didn't hesitate.
Grayson: I know you are busy, but would you let me steal you for dinner tonight? I promise not to discuss hostile takeovers. And I promise not to let you win again in darts.
A laugh escaped her before she could stop it. She shook her head, staring at the message for a moment longer. He wasn't from Chicago, so it wasn't like he was holding her back. But still, there was something about this that felt like walking into unknown territory.
She drummed her fingers against the table, debating before setting the phone down. No response. Not yet. One step at a time.
A few minutes later, her phone buzzed again.
Haley:You're booking it, right?
Olivia exhaled, shaking her head as she clicked "confirm."
One week in Boston. "I guess it is happening."