Chapter 5 A Holly Jolly Bet
A HOLLY JOLLY BET
ISLA
Hold my beer.
Or in this case, my Holly Jolly Martini.
Men like my brother’s best friend—down on love—don’t scare me. In fact, I thrive on the naysayers. Their pessimism only fuels my optimism. Makes me want to prove them wrong even more.
Rowan might be gruff and thorny, but I’ve been in the dating trenches long enough to handle every kind of personality. I’ve matched the eternal skeptics, the hopeless romantics, and everyone in between.
Because at the heart of it, the truth of love is universal—everyone wants to love and be loved.
It’s that simple. Everything else is only window dressing.
The guys are gone now and it’s just Rowan and me at this table in the corner of the room, hidden from the eyes of the few other patrons lingering in the bar.
After taking a dainty sip of the fantastic concoction I ordered—savoring the vanilla vodka and white chocolate liqueur—I slide the glass to the side of the table and flip open my planner, unhooking the red ribbon from the middle page with a deliberate flourish.
Rowan scoffs like he’s never seen anything like it before. “What in Santa’s ass is that?”
I meet his skeptical gaze, undeterred. “It’s a planner. You use it to plan things. Like, say, your day, your month, or your projects. In this case, you’re the project.”
He growls. Actually growls. Then he tips his chin toward the shiny red cover. “And you have seasonal planners?”
What a silly question. “Of course I do.”
He points at it again. “You don’t use a—I don’t know—iPad? Phone? Computer?”
I glance dramatically around the bar, taking in the glittering garlands draped along the brick walls, the twinkle lights casting a warm glow over the polished wood table, and the oversized Christmas tree dominating the lounge area, its ornaments catching the flicker of the nearby fireplace.
“Oops, wherever did I leave my laptop?” I quip, before fixing him with a no-nonsense stare.
“No. I’m old-school when it comes to writing down a client’s likes and dislikes, crafting bios, and getting to know them.
” I lean forward, meeting his gaze. “Writing by hand makes this more personal. And that’s what matchmaking is—it’s the opposite of a dating app.
It’s personal, it’s intimate, and it works.
” I brandish my favorite pen—this ballpoint leaves no streaks.
“You can’t backspace over someone’s hopes and dreams with a pen. ”
He shifts in his seat, clearly trying to find a way to argue without sounding like a jerk. Eventually, he mutters, begrudgingly, “Fine, that makes sense.”
I uncap the pen with a triumphant smile. “Good. Because the holidays fly by, and we’ve got exactly one day left in November and twenty-three in December to make this happen since the gala is on Christmas Eve.”
“Don’t remind me,” he says.
“Oh, but I will. Many times, surely,” I say with a smile as I click the pen once and tap it against the planner.
I love this kind of deep-dive work. This is precisely what I wasn’t able to do on the podcast, since I only had a few minutes with each caller to give advice and feedback.
“Okay, Rowan. We have a lot of work to do in a short amount of time. I need to know likes and dislikes, wishes and wants. But I find the best way to start is this—what’s your perfect outcome from this dating adventure? ”
Rowan shudders.
It’s not for show; it seems real and full of hurt, coming from the depths of him, and my heart softens.
I only know the broad strokes of his romantic story, heard in passing from my brother.
Rowan and his ex, Mia’s mom, were together for a good while, but nearly five years ago, she simply took off.
As someone who’s been left, I understand.
I feel the pain of my own failed love story sometimes, all the ways I was foolishly deceived by my ex.
But I refuse to wallow in that failure, especially when my business depends on success in romance.
That’s why I give my all to clients—I believe that everyone deserves love.
Including people who think it doesn’t exist, like this man.
I give Rowan a reassuring smile, hoping to soothe the wound. “This can be a good dating adventure.”
“Just like ‘nut’ and ‘cracker,’ those are words that don’t go together,” he says.
I’ve got my work cut out for me, but that only drives me on. “I hear you. But even so, tell me what you want to accomplish. And don’t tell me you’re here under duress; I already know that part.”
“You want to know my goal?”
“Yes,” I say, hopeful I can get him there.
“My biggest goal right now?”
“I would love to know,” I say, ready and waiting.
He nods toward my Holly Jolly Martini, smirking. “To try that.”
Well, that’s easy enough. I slide the glass toward him, hoping it works as the icebreaker he seems to need. “Enjoy,” I say.
Rowan raises it to his lips, and for a split second, his skeptical expression vanishes, his green eyes flickering with something close to surprise. No, that’s real delight in his irises as he takes a drink.
His sweet tooth is something else, and I can use this intel as I plan outings for him with different women—Christmas cookie decorating, eggnog tasting, candy cane making. I write this down, saying, “A man who likes sweet things.”
“You’ve figured me out, Isla,” he says dryly, but then his expression shifts. His gaze turns serious. “But before we dive into this dating adventure, otherwise known as a high-stakes game of emotional roulette, there’s something I need to say.”
I haven’t heard that tone from him before—like something’s vitally important. I lock my focus on him, especially since he’s letting details slip about the state of his heart—terribly damaged. That’s good to know, even if it’s sad to hear. “Go on.”
He blows out a breath, then says, “I’m sorry for what I said earlier. The pointless comment about your business. I tried to apologize after the Case of the Candy Cane Punch Poisoning, but I did a bad job of it.”
Actually, I did kind of walk away from him when he tried. I should say I’m sorry too. “I didn’t give you a chance. I stormed off,” I admit.
His lips curve up. “That was a storming off?”
“I suppose that’s an exaggeration. But I still want to take responsibility,” I say.
“You have nothing to apologize for,” he says, his tone stern again. A little bossy. A slight chill runs down my spine. But…a good chill, perhaps?
“And you truly don’t either. I’m hearing you loud and clear that romance isn’t your favorite thing,” I say, since I’m hoping it’ll help us work together if he feels understood. “But I appreciate your apology nonetheless.”
He gives a crisp but grateful nod.
Then, it’s my turn to smirk. “Though honestly, the best apology will come when you say that wasn’t pointless at all, Isla! I’ve met the woman of my dreams. Thank you.”
The eye roll. Dear god, the eye roll from him could win an award. “Don’t count on it,” he says.
“It’s going to be so fun,” I add.
“It won’t happen,” he says, standing his ground.
I straighten my shoulders. “It will. I pride myself on having a very successful client list, and they’re extremely satisfied with my matchmaking. And you will be too.”
He snort-scoffs. “Let’s not get ahead of ourselves.”
“I have faith enough for the both of us,” I say, but I clearly need to prove myself to him. And if there’s one thing athletes respond to, it’s a little healthy competition. Feeling bold, I say, “So much I’d be willing to bet on it.”
He lifts an eyebrow. “Oh, we’re betting now, are we?”
“Yes. Are you afraid to take me on?”
Rowan crosses his arms, leaning back with a challenging gleam in his eye. “Not afraid, just wondering what’s in it for me when you lose.”
Pausing to collect my thoughts, I grab my martini, taking a confident sip.
Because I am confident I’ll find love and connection for him, no matter how challenging it is.
Setting the glass down with a delicate clink, I turn the question around.
“When I win—and I will—you’ll come to a big matchmaking showcase at the end of the year and thank me for introducing you to the woman of your dreams. Publicly. ”
He barks out a laugh, the sound sharp but not unkind. “Dream woman? And I’ve got a unicorn coming for you on Christmas. Fits down the chimney and everything.”
“Spoiler alert: I love unicorns.”
“I’m shocked.”
I exhale loudly. This guy thinks he can twist me up, but I’m not the city’s hotshot new matchmaker for nothing.
My track record is excellent because I don’t just bet on love—I believe in it deeply, in spite of my own heartache.
Rowan may think love is a mirage, but I intend to show him it’s the real thing. “Do you accept my stakes?”
“Sure, because I won’t lose.” He sounds amused, like he’s having a damn good time with me tonight. That seems like a positive start for a business relationship. The more fun we have together, the more open-minded he’ll be on dates during the next few weeks. “But if you lose…”
He doesn’t finish the thought. Instead, he reaches for my drink, turning it a notch, then another. Wait—is that deliberate? He’s lifting it and drinking right from the spot with my lipstick mark. It shouldn’t affect me, but suddenly, I’m more interested in that glass than the bet.
Snap out of it, Isla. You don’t have a crush.
But the thought lingers, annoying me almost as much as it thrills me.
When he sets the glass down, he’s all laid-back attitude as he says, “You pick, sweetheart.”
That term of endearment shimmies down my spine, and I hate that I like how he says it.
“Fine. If I lose…” I hesitate, trying to think of something he’d actually enjoy and that won’t go against my romantic values. I’m not going to publicly admit matchmaking doesn’t work—that’d be a lie. Then it hits me. “You get to choose my date for my matchmaking event.”
His eyebrows shoot up. “You’re letting me pick who you bring to your big matchmaking event?”
Maybe I’ve lost my mind. But I need to show him how serious I am. How much faith I have both in my thorough, thoughtful ways and in the power of true love. “Anyone you want. No veto power,” I say.
His surprise melts into something far more devious—a grin that should make me nervous, but instead, it sparks a competitive fire. “You trust me that much?” he asks.
Not in the least. But Rowan’s a confident man who’s used to overpowering opponents.
I need to prove I won’t bend, and I definitely won’t break as he tries to fight me every step of the way.
I need him to see I’m the one who can succeed at this monumental task of finding a holiday match for the World’s Grumpiest Man and Certified Christmas Hater.
“Not at all,” I say breezily. “But it won’t matter because I’m not losing.”
“Interesting,” he says, stroking his chin. “How do you feel about seventy-two-year-old dudes who can’t drive? Or tech bros who douse themselves in body spray? Scratch that,” he mutters, almost to himself, his brow furrowed like he can’t bear the thought of either. “They’d both be terrible for you.”
“And you know my type?”
He holds my gaze, his lips twitching in amusement, his eyes glimmering with…something else entirely. “Maybe I do.”
An unexpected tingle rushes through me. Or maybe it’s not so unexpected given where my thoughts have strayed a few times.
I shake them off once again. “Whoever you pick, I’ll show up.
But you should be prepared to admit that the match I find for you will make you believe in unicorns because she will be your dream woman. ”
He lifts his scotch glass. “To the matchmaking challenge of the season.”
I clink my martini against his tumbler. “Now, tell me what you look for in a dream woman.”
There’s a long, weighty pause as he studies me. Then he says, “Brunette, blue eyes, sassy as fuck.”
He’s messing with me. I know he’s messing with me. And yet, those tingles have the traitorous audacity to race through me again.
This is going to be the toughest challenge I’ve faced.