CHAPTER 22
I nside the community room at Paradise Harbor House, Elena, Kaitlyn, and Will sat around a table, reviewing the footage from the interviews earlier in the day.
“That was amazing,” Kaitlyn said as the last clip played. “Melanie told her story so beautifully. It felt real, honest.”
“She did great,” Will agreed, clicking through his editing software. “I’ll clean up the audio and add some soft background music, but the footage is solid. We’ll have it ready before the fundraiser tomorrow.”
Elena leaned back, nodding in satisfaction. “This is exactly what we needed. The community needs to see the heart behind Paradise Harbor House, not just statistics. Real stories connect people.”
Kaitlyn smiled, but there was a trace of nervousness in her expression. “Do you think this will help push the fundraiser over the edge? I mean, we need every dollar we can get.”
“The numbers are looking great so far. I appreciate what your Aunt Leah is doing regarding funding through grants. It’s very forward-thinking of her. We do take things one day at a time, but we still need to think long-term if we want to stay afloat for many years to come. “
“I know she loves to work with numbers,” Kaitlyn offered. And, she’s good at this.”
“I don’t know much about the finance and investments, but if you’re worried about money, your aunt Leah might have the answer for that. I realize that grant writing takes time, and it might be another year before we see any money. But, it’s still important to diversify our outreach.”
Kaitlyn nodded. “I understand.”
“You’d be surprised how many people see a place like this and have no real idea the impact it has on a community. We’re doing good work here, and that’s what counts.”
Elena reached for Kaitlyn’s hand, giving it a reassuring squeeze. “I think this will remind people why they’re here. And when they see what their donations can do, they’ll give from the heart.”
Will shut his laptop with a soft click. “Then let’s make sure tomorrow night is everything it needs to be.”
Kaitlyn took a deep breath and then smiled. She didn’t want to measure the success of the fundraiser just by the numbers. What she worried about but couldn’t say to anyone was that she was afraid of disappointing Elena.
This was the first time she’d put herself out there after college. She did her best to push her worries away and focus on being herself, a young woman finding her way in the world, one step at a time.
The door chimed, and Jack appeared, his messenger bag slung over one shoulder. "Hope I'm not interrupting."
"Perfect timing," Elena said. "We just finished reviewing the interview footage."
"Good, because I come bearing news." He dropped into the chair beside Leah, who'd been quietly working on donor packets in the corner. "Mike—the captain—wants to do a morning walkthrough of the boat. Thought you might all want to see where everything will be set up."
Kaitlyn's eyes lit up. "Really? That would be incredible. Will, we could plan our camera angles ahead of time."
"Exactly what I was thinking," Jack smiled. "Nine a.m. work for everyone?"
"I'll text Mom and Aunt Chelsea and Tess," Kaitlyn said, already reaching for her phone. "They should see this too."
Jack looked at Leah and smiled.
“Thank you, Jack. I’m guessing you had something to do with that.”
“I might have mentioned it. I can’t remember.”
Kaitlyn, Elena and Will looked at each other and smiled.
The twinkle in Jack’s eyes told them everything they needed to know. That Leah was falling in love, and Jack Calloway was the reason.
The next morning dawned clear and perfect, with just enough breeze to ruffle the flags along the marina. Will and Kaitlyn arrived with her mother and aunts to find Jack already waiting at the dock, coffee carrier in hand.
"Cuban roast," he announced, passing out cups. "Brain fuel for party planning."
"You're a lifesaver," Chelsea declared, accepting hers. "Some of us needed this after staying up late sorting auction items."
“Where’s Elena?” Kaitlyn asked.
“She wanted to stay back at the house to get breakfast ready for everyone, so she said she trusted us to handle this.”
The boat was magnificent in the morning light, its white hull gleaming. Captain Mike met them at the gangway, his weathered face creased in a welcoming smile.
“Thank you so much for helping us with this fundraiser,” Kaitlyn said.
"Jack's told me all about Paradise Harbor House," he said, shaking hands. "My daughter volunteers at a women's shelter up in Tampa. When Jack mentioned this fundraiser, well…" He shrugged. "Seemed like fate."
They followed him aboard, Kaitlyn's breath catching at how spacious the deck was. Tess immediately started calculating table arrangements while Leah pulled out her ever-present notebook.
"The sunset will be perfect from this angle," Will said, framing shots with his hands. "We can set up the presentation screen here, catch that golden hour light..."
"And the dining area below deck," Captain Mike continued, leading them down. "Plenty of room for your silent auction displays."
Gretchen touched Kaitlyn's arm as the others explored. "Can you picture it? All those people coming together to support Paradise Harbor House? You should be proud of what you’ve done."
"What we've all done, Mom," Kaitlyn corrected softly. "I couldn't have done any of this alone."
Chelsea appeared with more coffee from the boat's galley. "Jack's showing Leah the upper deck. I think he's trying to convince her it's the perfect spot for a private date."
"Subtle, he is not." Tess laughed, then grew thoughtful. "Though speaking of not subtle... Jamie's bringing extra staff tonight. Said something about wanting everything to be perfect."
"For the fundraiser?" Gretchen's tone was innocent. "Or for you?"
“Very funny,” Tess responded as she walked away to explore more of the boat.
"This is really happening," Kaitlyn said softly, leaning on the rail beside Will. "All our work, all our hopes..."
"It's going to be amazing," he assured her, his hand finding hers. "Just like you."
Kaitlyn touched his arm, her voice thick with emotion. "I can't thank you enough for everything you've done. Not just for the fundraiser, but for me personally. My life has been upside down for so long, but now..." She paused, searching for the right words. "Now I feel like the spinning has finally stopped. Like I've found solid ground."
"And you think I had something to do with that?" he teased gently, though his eyes were serious.
She met his gaze, the blue of his eyes matching the water below. "You've had everything to do with it."
Their eyes locked, and for a moment, everything felt perfect. But even in this peaceful moment, thoughts of her father and Sarah tugged at the edges of her mind. The uncertainty of their future relationship cast a shadow she tried to push away, not wanting it to dim this precious moment with Will.
As if reading her thoughts, Will touched her cheek. "Kaitlyn, don't worry about Sarah. I know in my heart that you two will find your way to each other."
"How did you know I was thinking about that?" she asked, wonder in her voice.
He smiled, his thumb brushing her cheekbone. "I'd like to think I know you pretty well by now. The more time we spend together, the more certain I become of that."
Kaitlyn leaned into his touch, marveling at how he could read her silent moments, how he seemed to know instinctively when her thoughts turned dark and exactly how to ease her fears.
In all her carefully curated social media life, she'd never imagined finding something this real, this true. Nothing could be more perfect than being known, being understood, being loved exactly as she was.
“Looks like someone changed her mind,” Chelsea yelled to everyone.
From the dock, Elena appeared with more volunteers carrying supplies. "I couldn’t stay away, I’m too excited. Besides, I’ve got extra stuff to drop off. Ready to start marking setup locations?"
Kaitlyn waved to Elena. "Absolutely!”
"The bar setup will go here." Captain Mike indicated a polished wooden counter. "And we've got built-in coolers underneath for your champagne service."
"Perfect for the sunset toast," Tess noted, already envisioning the flow of service. "Jamie's staff will have easy access."
Leah was making notes in her ever-present notebook. "Jack, what time are your publishing contacts arriving? We should reserve the best viewing spots for major donors."
"Six sharp," he replied. "Though knowing Regina, she'll be here at five forty-five. She's particularly interested in the literacy program."
Will had his camera out, documenting the space. "Kaitlyn, come see this angle. When the sun hits here, it'll create the perfect backdrop for the presentation."
Chelsea watched her niece move confidently through the space, directing, planning, solving small problems before they could become large ones. "She's really found her calling, hasn't she?" she murmured to Gretchen.
"She has," Gretchen agreed softly. "Though I never would have predicted this a year ago."
"Life's funny that way," Captain Mike commented, overhearing them. "Sometimes the best journeys are the ones we never planned."
"Speaking of journeys," Elena called from below deck, "we need to figure out the traffic flow for the silent auction. We don't want bottlenecks when people are trying to place bids."
They spent the next hour mapping out every detail—where the musicians would be positioned, how to arrange the seating to maximize the sunset view, the best spots for Will to capture candid moments of guests enjoying themselves.
"We should mark the spots for the family photos," Kaitlyn said, moving toward the display area they'd designated. "The lighting needs to be just right—we want people to feel the stories, not just see them."
"Like Melanie's interview," Gretchen added. "The way you captured her strength, her hope."
Will nodded, already adjusting his camera settings. "We'll set up soft lighting here, keep it intimate. When people see these images, they should understand that Paradise Harbor House isn't just a place—it's a community."
"Speaking of community," Captain Mike called from the bridge, "wait until you see what happens when we drop anchor in that perfect sunset spot. The way the light plays on the water…it's like nature designed it for moments like this."
Tess leaned against the rail, the breeze playing with her hair. "Jamie mentioned something about timing the dessert service just as the sun touches the horizon. Said it adds a touch of magic to everything."
"Pure romance, that one," Chelsea teased, but her eyes were kind.
Captain Mike appeared with more coffee and what looked suspiciously like fresh Cuban pastries. "Courtesy of your friend Jamie," he explained. "Said something about practicing the dessert presentation."
"Quality control," Tess said solemnly, reaching for one. "Very important."
Tess felt her cheeks warm as everyone's attention turned to her. The pastry in her hand suddenly seemed very interesting.
"Just friends, huh?" Chelsea's tone was too innocent. "Is that why he's been testing dessert recipes on you all week?"
"He tests them on everyone," Tess protested, but even she could hear the weak defense in her voice. "It's…professional courtesy."
"Oh, of course," Leah agreed, straight-faced. "Very professional. Like those private sunset guitar sessions at Max's?"
Tess shot her sister a look that promised revenge. "Those are just…he's just getting back into playing. Nothing more."
"Mmhmm." Chelsea wasn't even trying to hide her smile now. "And I suppose him rearranging his entire staff schedule to be free for the fundraiser is just professional dedication?"
"You all are impossible," Tess muttered, but she couldn't quite suppress her own smile. The truth was, she and Jamie were…something. Something delicate and new, still finding its shape.
"Leave her alone." Gretchen surprisingly came to her rescue. Then ruined it by adding, "Though I have to say, his key lime pie has gotten even better lately. Amazing what happiness does for a chef's cooking."
"I hate all of you," Tess declared, but she was laughing now. Because they weren't wrong—Jamie had been different lately. Lighter. More like the person everyone said he'd been before losing Emma. And if she had something to do with that…well, maybe that was its own kind of magic.
"You know what would be perfect for the fundraiser?" Kaitlyn chimed in, her eyes dancing with mischief. "If Jamie played guitar during dessert. You know, something romantic…"
"Don't you dare," Tess warned, pointing her half-eaten pastry at her niece. "He's just getting comfortable performing again."
"Actually," Will said thoughtfully, lowering his camera, "that would make for amazing footage. The restaurant owner who supports Paradise Harbor House, sharing his music…"
"See? Perfect!" Chelsea agreed. "And Tess could?—"
"Could what?" Tess challenged. "Stand there awkwardly while you all pretend not to stare?"
"Well, you could always join him," Leah suggested innocently. "I seem to remember you used to sing in high school."
"That was thirty years ago!" Tess felt her face flame again. "And if anyone mentions this to Jamie, I swear I'll tell Jack about that poetry journal Leah's been hiding in her desk."
"What poetry journal?" Jack called from above deck.
"Nothing!" Leah shouted back, her own cheeks reddening.
"Actually," Tess said, trying to regain some dignity, "Jamie's friend's band is handling the music. He wants to focus on the food service, make sure everything runs perfectly."
"Oh, I bet that's why he wants to focus on the food," Chelsea drawled. "That way he can focus on you, Tess."
"I walked right into that one, didn't I?" Tess groaned, but she couldn't help smiling. The truth was the thought of Jamie watching her instead of performing did make her pulse quicken a bit.
"Face it, sis," Leah said, "you're not fooling anyone. Especially not with that look on your face right now."
"What look? There's no look!" But Tess could feel herself blushing again.
"That one," Kaitlyn pointed out helpfully. "The same one he gets when you walk into Max's."
"Can we please focus on the fundraiser?" Tess begged. "You know, the actual reason we're all here?"
"Oh, we're focused," Chelsea assured her. "On all the important details. Including how our sister somehow managed to capture the heart of Key West's most eligible restaurateur."
"I hate every single one of you," Tess declared, but her smile gave her away. "Captain Mike, any chance we could throw a few of these people overboard?"
They laughed and enjoyed the remainder of the pastries and coffee and then thanked Captain Mike. Everything was falling into place. The fundraiser was only hours away, and no one was more excited than Kaitlyn.