Chapter 9
CHAPTER 9
K aitlyn adjusted the straps of her tote bag as she stepped out of the bakery, the scent of fresh Cuban bread and espresso still lingering in her nose. The bag was loaded with donated pastries for Paradise Harbor House, and the heat of the mid-morning sun made her wish she had grabbed an iced coffee for the walk.
As she turned onto the street leading to the shelter, she slowed at the sight of a man with a camera, crouched near the entrance of Paradise Harbor House. He was filming the building, panning up to catch the sign, then turning his lens toward the side lot where some of the women were tending the small community garden.
Kaitlyn’s immediate reaction was suspicion. Her grip tightened around the tote. Who is this guy? Some influencer trying to get content at the expense of vulnerable women?
She approached him quickly, her sandals clapping against the pavement.
"Hey! What do you think you're doing?" she demanded, stepping into his shot.
The man glanced up, his striking blue eyes narrowing slightly as he pushed his shaggy brown hair, which fell just below his chin, out of his face. He had a little unshaven scruff—just enough to give him a rugged look, and when he smirked, Kaitlyn found herself momentarily thrown off by how gorgeous his smile was. Charming, irritating, and far too self-assured all at the same time. He wore a plain gray t-shirt and cargo shorts, a camera strap slung across his chest.
"Filming," he said simply.
Kaitlyn folded her arms. "Yeah, I can see that. But why? Because unless you’re with the news or someone from the city, I don’t think you have permission."
The man sighed and stood, adjusting his camera. "I’m Will. Will Moreno. I’m working on a documentary about the people who live and work in Key West beyond the tourism scene. You know, the ones who don’t make it into the glossy brochures. I met Elena a few days ago, and she said it was okay for me to get some exterior shots."
Kaitlyn blinked. "Elena approved this?"
Will smirked. "Did you think I just showed up with a camera and started recording?"
"Honestly? Yes. That happens more than you'd think," she shot back. "Social media vultures love to exploit places like this for pity clicks."
Will’s smirk faded. "That’s not what I do. I don’t chase feel-good stories to go viral. I tell real ones. I was actually about to head inside to talk to Elena again—unless you want to arrest me first."
Kaitlyn huffed but waved toward the door. "Fine. But I’m watching you."
Inside, the air-conditioning was a welcome relief. Elena was speaking with one of the volunteers when she spotted them.
"Will! Good timing," she said, smiling. Then she glanced at Kaitlyn. "I see you’ve met our skeptical volunteer."
Kaitlyn gave a sheepish shrug. "Sorry. I thought he was just some random guy trying to get content."
Will chuckled. "No hard feelings. I’d probably assume the same thing."
Elena gestured toward the seating area. "Will is interested in telling the story of Key West from a different angle—one that includes places like Paradise Harbor House. I think it could be a good opportunity for us."
Kaitlyn still wasn’t convinced. "And how do we know this isn’t just a one-off project that will get a few festival screenings and then disappear? These women don’t need someone swooping in, putting a lens on their lives, and then leaving like they were some passing inspiration."
Will studied her for a long moment. "That’s not how I work. I don’t just drop in and grab a few soundbites—I stay. I follow through. That’s why my last documentary took two years to make. It’s about the people, not the footage."
Kaitlyn folded her arms. "Two years? That’s a commitment."
Will nodded. "Yeah. And if I’m lucky, this project will take just as long."
Elena leaned in. "I really do think Will’s work could help bring awareness in a way we haven’t been able to. I’ve got to get to my office. Perhaps you can answer any questions Will has." Elena looked at Will. “I’m sure Kaitlyn will be happy to help.”
Elena walked away and Kaitlyn looked back at Will. She hated when she was put on the spot, but she also hated the idea of dismissing someone just because she didn’t trust easily.
Kaitlyn looked back at Will. "All right. Prove it. Show me your work."
Will didn’t hesitate. He grabbed his phone and pulled up a website, scrolling until he found a link. "Here. My last documentary, Under the Surface , is about the fishing communities that are being priced out of Florida’s coastal towns. No sob stories. Just real people trying to hold on to the life they’ve built."
Kaitlyn took the phone, watching the short preview video. The footage was raw but striking—stunning ocean shots juxtaposed with interviews of fishermen discussing rising costs, the struggle to keep their businesses afloat, and the impact on their families.
Handing the phone back, she tilted her head slightly. “Okay, so you’re not a hack. What beach is that?”
Will smirked. “I’ll take that as a compliment. That’s Smathers Beach. Haven’t you been there?”
Kaitlyn shook her head. “No. I haven’t had a chance to check it out. I didn’t think there were many good beaches here.”
Will let out a soft chuckle, shaking his head. “Now that is a shame. It’s one of the best around. I go there all the time. I’d be happy to show it to you.”
“Thanks, but I’ve got too much to do to take a beach day.” Her response came out sharper than she intended, and she immediately regretted the defensiveness in her tone. “Besides, I’m more than capable of finding it on my own.”
He shrugged, unfazed. “Suit yourself.”
Kaitlyn turned and strode from the room, but not before catching the flash of confusion that crossed Will's face. She told herself she couldn't trust him, yet found her gaze drawn to the window throughout the day, watching Will Moreno as he worked outside.
By the time she left Paradise Harbor House that afternoon, her thoughts were still tangled. Will Moreno was…interesting. He wasn’t just another tourist chasing a cheap headline. He was thoughtful, and serious about his work, but it didn’t change Kaitlyn’s opinion that he was someone worth keeping an eye on. For professional reasons, of course.
The bell above the door chimed softly as Leah stepped into The Lost Anchor, the sound almost lost beneath the whir of ceiling fans.
The bookstore wasn't on her carefully planned route for the day, but she'd noticed it while walking back from another failed attempt to get local business support for Paradise Harbor House. A hand-painted sign in the window had caught her eye: "Books for every journey, maps for every soul."
The interior was a reader's dream—floor-to-ceiling shelves created intimate nooks and crannies, while comfortable chairs invited lingering. The air smelled of old books and fresh coffee, with something else underneath—salt air drifting in through open windows, reminding visitors they were still in Key West despite the literary sanctuary.
"We're not a tourist shop," a voice called from somewhere behind the shelves. "If you're looking for Hemingway merchandise, try Duval Street."
"Actually, I need books on nonprofit management and grant writing," Leah replied, following the voice. "Preferably something published this decade."
She rounded a corner to find a man sorting through a stack of books, his silver-streaked dark hair falling across his forehead as he worked.
He looked up, and Leah found herself caught by sharp green eyes behind wire-rimmed glasses. He had the kind of face that showed he smiled often, though right now he was studying her with amused skepticism.
"Nonprofit management?" He set down the book he was holding. "That's refreshingly specific. Usually people just want beach reads or local history."
"I like to be specific," Leah said, straightening her shoulders slightly. "It saves time."
"Ah, a pragmatist." He moved toward a different section of shelves with the easy familiarity of someone who knew exactly where everything belonged. "And what worthy cause brings you to the exciting world of grant writing manuals?"
"Paradise Harbor House. We're trying to expand our programs, but—" She paused as he held up a hand.
"Elena's place? The women's shelter?" His expression shifted from mild amusement to genuine interest. "Now that's a story worth telling. Though I'm guessing you're more interested in the funding chapters than the narrative ones."
Leah blinked, surprised by both his knowledge and his insight. "You know about Paradise Harbor House?"
"I know about most things that matter in Key West," he said, pulling several books from different shelves. "Jack Calloway, by the way. Former journalist, current purveyor of literary escapes and caffeinated salvation."
"Leah Lawrence." She found herself charmed despite her usual business-like approach. "Former corporate consultant, current…well, I'm still figuring that part out."
Jack's smile crinkled the corners of his eyes. "Aren't we all?
He handed her a stack of books. "Here, start with these. The green one's outdated on tax law but brilliant on program development. The blue one's new, good for modern fundraising strategies. And this one," he tapped a worn copy of 'To Kill a Mockingbird,' "is just because everyone involved in social justice should revisit it occasionally."
Leah glanced at the classic novel. "I'm not sure I have time for fiction right now. We have deadlines?—"
"Always time for fiction," Jack interrupted, leading her toward the café area. "Stories remind us why we do the work in the first place. Coffee?"
She should say no. She had a schedule, a to-do list, three more businesses to visit about donations. Instead, she found herself settling onto a barstool at the counter while Jack moved behind it with practiced ease.
"Cuban roast," he said, starting the coffee maker. "Local blend. Like everything else worth knowing in Key West, there's a story behind it."
"You seem to know a lot of stories," Leah observed, setting her stack of books beside her.
"Hazard of the former profession. Never lost the habit of collecting them." He placed a mug in front of her, the aroma rich and inviting. "So tell me about Paradise Harbor House. Not the grant version—the real story."
And somehow, in that quiet bookstore with afternoon light filtering through windows clouded by salty air, Leah found herself doing just that. She told him about Elena's tireless dedication, about Kaitlyn's work with the families, about their dreams of expanding services. Jack listened with the focused attention of someone used to finding the heart of a story, asking questions that made her see their work from new angles.
"You know," he said finally, refilling their cups, "I used to host author events here, before the tourist shops took over the local literary scene. Been looking for a reason to restart them. Paradise Harbor House might be just the cause we need."
Leah's practical nature surfaced through her unexpected enjoyment of their conversation. "A fundraiser?"
"Among other things." Jack's smile held a hint of challenge. "Sometimes the best support isn't just financial. Sometimes it's about creating spaces where stories can be shared, where people can connect beyond their immediate needs."
"That's…" Leah paused, realizing she'd completely lost track of time. The afternoon light had shifted, painting the bookshelves in gold. "Actually, that's exactly what we've been trying to articulate in our grant applications."
"See?" Jack tapped the copy of 'To Kill a Mockingbird.' "Fiction helps. Now, about that event—I was thinking we could start with local authors, maybe some readings from shelter residents, if they're interested. Create a real community dialogue."
Leah found herself nodding, her mind already organizing possibilities. "We'd need to be careful about privacy, make sure everyone's comfortable with the format."
"Of course." Jack's expression turned serious. "I may be out of the journalism game, but I still understand the importance of protecting sources. We'll do it right."
“Thank you so much. We’re working on a sunset cruise fundraiser as well. I hope you’ll join us.”
He smiled and the twinkle in his eye made her heart race.
“I’d love to. When is it?”
“We’re still working on that. I’ll get the information to you just as soon as I know more.”
Looking at him in the warm light of his bookstore, Leah realized she'd completely abandoned her scheduled activities for the day—and for once, she didn't mind. There was something about Jack Calloway that made her want to set aside her spreadsheets and listen to more stories.
"I should go," she said reluctantly, gathering her books. "How much do I owe you?"
Jack waved away her reaching for her wallet. "Consider it an investment in the community. Just promise you'll come back and tell me how the grant writing goes. I may have some contacts from my reporting days who could help."
"I will." Leah turned to leave, then paused. "The coffee was excellent, by the way."
"Come by tomorrow," Jack called after her. "I'll tell you its story."
As she stepped back into the Key West afternoon, Leah realized she was smiling. Her carefully planned day had been thoroughly derailed, but somehow she felt more energized than ever. Maybe sometimes the best plans were the ones that left room for unexpected chapters.