Chapter 5
CHAPTER 5
T ess leaned on the sticky bar at Margarita Max's, watching the crowd ebb and flow with the unpredictable rhythm of a Key West evening.
The overhead fans spun lazily, barely cutting through the humidity, while the jukebox blared an off-key rendition of "Sweet Caroline" courtesy of a karaoke enthusiast who had clearly peaked three margaritas ago. The neon signs cast a multicolored glow over everything, turning the usual chaos into something almost magical.
A group of sunburned tourists crowded the bar, their matching t-shirts proclaiming them part of "Ava's Last Fling Before the Ring." Tess had already memorized their drink order—five strawberry daiquiris and one virgin margarita for the designated driver. They'd been cycling through the same drinks for the past two hours, each round getting progressively louder and gigglier.
"Leah, table four needs another round," Connie barked from across the bar, her tone sharp but not unkind. She moved with military precision, mixing drinks while simultaneously keeping an eye on every corner of the establishment. Nothing escaped her notice—not the couple trying to sneak their own drinks in, not the wannabe musician attempting to adjust the sound system, and certainly not her new employees' growing competence.
Leah adjusted her tray and nodded, weaving through the tightly packed tables with practiced care. She'd mastered the art of dodging tipsy patrons and balancing drinks like a pro. Her corporate efficiency had translated surprisingly well to bartending, though the sticky floors and constant noise were a far cry from her former office. Still, it wasn't exactly the life she'd imagined when she'd moved to Key West.
"Watch your back," she called out to a server carrying a precarious tray of shots. The younger woman flashed her a grateful smile—they'd all learned quickly that survival at Max's depended on looking out for each other.
"How's it going?" Tess asked as Leah passed by, her voice loud enough to cut through the noise. She was arranging lime wedges with the same attention to detail she'd once applied to their failed craft projects.
"Great," Leah deadpanned. "I'm living my best life." She gestured to a spot on her shirt where someone's blue cocktail had left its mark. "The tourist from table seven wanted to show me his impression of a dolphin. It involved a lot of arm movement."
Tess grinned and returned to wiping down the bar, where a man in a Hawaiian shirt was gesturing wildly about "the best fish tacos on the island." She nodded along, throwing in the occasional "uh-huh" while her mind wandered to Kaitlyn.
Their niece's sudden interest in Paradise Harbor House had caught both of them off guard. Tess had expected beach days and bar hopping, not volunteering at a women's shelter. It was like watching a butterfly emerge from its social media cocoon.
The man in the Hawaiian shirt leaned forward, his enthusiasm for fish tacos apparently boundless. "You gotta try Rico's place—it's this little shack down by the marina. Changed my life!" He punctuated this declaration by accidentally knocking over his water glass, which Tess caught with newfound bartender reflexes.
"Nice save," Connie commented as she passed by. "You're getting better at this." Coming from Connie, it was high praise indeed.
As if summoned by her thoughts, Kaitlyn appeared in the doorway, her sundress fluttering slightly in the breeze.
The contrast between her fresh, put-together appearance and the bar's cheerful chaos was striking. She spotted Tess and waved, weaving her way through the crowd with the kind of youthful confidence Tess envied. Even the Ava's Last Fling crew paused their celebration to watch her pass.
"What are you doing here? Why aren’t you out having fun?" Tess asked as Kaitlyn reached the bar. "Shouldn't you be out enjoying your night?" She gestured to the growing crowd of twenty-somethings gathering near the karaoke machine.
"I just came to say hi," Kaitlyn said, sliding onto one of the barstools. Her perfectly styled hair and careful makeup seemed at odds with the excitement in her eyes. "Plus, I wanted to tell you about my visit to Paradise Harbor House this morning."
"How did it go?" Tess asked, genuinely curious. She mixed a mojito on autopilot while keeping her attention on her niece. The change in Kaitlyn over the past twenty-four hours had been subtle but noticeable—like watching a script being rewritten in real time.
"Really well," Kaitlyn said, her face lighting up in a way that had nothing to do with the bar's neon signs. "I met with Elena Armstrong and she has some ideas where I can volunteer. We talked about a lot of things and she even introduced me to some people who are living there. You should see the inside. It’s the coziest home. I mean it’s a big house, but it still manages to seem small and welcoming. It’s like going to visit at your grandmother’s house. There's this little girl, Maria, and her mom. They're staying there because they had nowhere else to go after leaving a bad situation. Maria's only five, but she's so sweet. She showed me her collection of seashells—she keeps them in an old shoebox and knows all their names."
Tess's smile softened. "Sounds like a great place to volunteer." She remembered their own early days in Key West when everything had seemed possible. Maybe it still was, just not in the way they'd expected.
"I hope so," Kaitlyn said. She hesitated, her fingers tracing the edge of a napkin. "I was thinking about asking Elena if I could help with their communications. You know, social media, marketing, that kind of thing. It's what I studied, so maybe I could actually put my degree to use."
"That's a great idea," Tess said immediately, recognizing the spark of genuine passion in her niece's voice. "You're a natural at that stuff."
"Thanks," Kaitlyn said, her cheeks pinking slightly. "I'm nervous, though. I don't want to mess it up. This isn't like posting vacation photos or sorority events. These are real people with real stories."
Before Tess could respond, Leah appeared, her tray now empty but her shirt sporting a new stain. "What's this about messing up?"
"Kaitlyn's thinking about helping Paradise Harbor House with their marketing," Tess explained, already reaching for the soda gun to fill another order.
Leah's eyebrows lifted. "That's ambitious." Her tone carried the same cautious assessment she'd once used in board meetings.
"It's also something she's good at," Tess said pointedly.
Leah folded her arms, glancing at Kaitlyn. "Well, if you're serious about it, I say go for it. The worst that can happen is you learn something from the experience." A ghost of a smile crossed her face. "Heaven knows we've learned plenty from our experiences in Key West.”
"Thanks," Kaitlyn said. "I'll talk to Elena tomorrow."
“So, what else have you been up to?” Leah asked.
“Well, after my visit with Elena, I went on a tour at the Ernest Hemingway Home and Museum. That was pretty cool. Did you know there are about sixty cats living there? They were everywhere. I petted a few that were friendly, but a few didn’t want me to touch them. Right now, I thought I’d go check out the fish tacos at Seven Fish. My guidebook says they’re really good. Then, I guess I’ll head home.” She dangled the house key in the air. “I’ve got my key. I’ll catch up with you guys later.”
Tess watched as another group of tourists stumbled through the door as Kaitlyn headed out.
The night wore on, a blur of drink orders and tourist stories. Before Kaitlyn left Tess found herself watching her niece as she sat at the bar, occasionally chatting with customers but mostly observing everything with new eyes. She wasn't just seeing potential photo opportunities anymore—she was seeing stories, connections, possibilities.
By the time their shift ended, the crowd had thinned, leaving behind only a few die-hard karaoke fans and a table of locals playing cards in the corner. The Linda's Last Fling group had departed hours ago, their matching shirts now adorned with various drink stains and their designated driver herding them into waiting cabs.
Tess and Leah wiped down tables, their energy drained but their spirits surprisingly high. The sticky floors seemed less annoying somehow, the karaoke less grating. Tess thought maybe they were finally finding their rhythm in this unexpected chapter of their lives.
"You know," Tess said as she stacked chairs, their legs squeaking against the floor, "Kaitlyn's got more focus than I gave her credit for."
Leah nodded. "She's surprising me too. I didn't expect her to take an interest in something like Paradise Harbor House. I thought we'd be spending our days off chaperoning beach parties."
"Maybe she's just figuring out what matters to her," Tess said. "Kind of like we are." She paused to rescue a forgotten phone from under a table, making a mental note to add it to Connie's lost and found collection.
Leah gave her a look. "You think working here is us figuring things out?"
"I think it's a step," Tess said with a shrug. "And sometimes that's all you need. Remember when we first got here? We thought we'd be running sunset cruises and teaching beach yoga by now."
"Instead, we're mixing margaritas and cleaning up after spring breakers," Leah said, but there was more amusement than bitterness in her tone.
"At least we're doing it together," Tess pointed out. "And hey, we haven't had any more brilliant business ideas in four days. That's progress, right?"
Leah smiled. “I guess so.”
The next morning, Kaitlyn stood on the porch of Paradise Harbor House, her heart pounding as she knocked lightly on the screen door before walking inside. She'd traded her usual resort wear for something more practical—neat shorts and a crisp white shirt.
Elena appeared swiftly, a clipboard clutched in her hand and a warm smile lighting her face. From behind her, the sounds of breakfast preparation spilled out—the clinking of dishes, children's laughter, and a symphony of cozy chaos signaling a home awakening.
"Kaitlyn! Good to see you. What brings you by so early?"
"I wanted to talk to you about…maybe doing more," Kaitlyn said, fidgeting slightly. Her carefully prepared pitch suddenly seemed inadequate in the face of the real work happening inside. "I have a degree in business communication, and I thought maybe I could help with your marketing. Social media, fundraising, things like that."
Elena's expression brightened, her clipboard lowering slightly. “Our online presence could use a refresh, and we're always looking for ways to boost donations. I’m not sure what else you were thinking of doing but we can explore ideas. We do amazing work here, but sometimes getting the word out can be challenging."
Relief flooded Kaitlyn's face. "Really? That's great. I can start whenever you need me. I've been thinking about some ideas already—ways to share success stories, highlight your programs, maybe even set up a regular donor newsletter."
"How about today?" Elena said. "We're planning a fundraiser in a couple of weeks. We’re just now working on ideas for that. It would be wonderful to have your input. Lily helps me with marketing things, but perhaps you and she might brainstorm? Sometimes fresh eyes see opportunities we might miss."
Kaitlyn nodded eagerly. "I'm in."
She followed Elena inside, where Maria was carefully taking her seashells out of a shoebox and carefully arranging them on a windowsill, each one placed with deliberate care. She looked up and waved, her smile missing two front teeth.
Kaitlyn waved back. For the first time since graduation, she felt like she was exactly where she was meant to be. Not performing for an online audience or meeting someone else's expectations, but doing something real, something that mattered.
Through the window, she could see happiness everywhere. Maybe her aunts weren't the only ones who'd come to the island looking for a fresh start. Maybe sometimes you had to get lost in paradise to find your way forward. She thought of Key West as the next stop on her journey to find purpose and meaning.
She smiled and reminded herself that there wasn’t anything wrong with having fun now and then as well. And, with Aunt Tess and Aunt Leah, fun would always be just around the corner.