WebNovels

Chapter 4 - The Fifty-Thousand-Dollar Bet

LOVE IS the beginning of the journey, its end, and the journey itself.

I type the message the way Mia suggested, then stop. Because really? She has to be pranking me. She's been threatening it for months, every time I send her a new name to woo on my behalf. One of these days, I'm going to get an outraged reply from some woman, demanding to know why I tried to pick her up with Shakespeare's most romantic lines.

But this one is different. I can't risk anything screwing it up.

Maybe I should go for the candy. Women love candy, right?

"Lara?" I bellow.

My assistant materializes in the doorway and gives me a look. "What did I say about yelling?"

"That it's a sign of unnecessary masculinity," I reply with a grin. "But where would the fun be if we whisper? I need a three-pound box of chocolates."

"Is it that time of the month?" she asks, arching one pierced eyebrow.

Lara looks like she just walked out of a punk rock concert, but there's nobody better to keep my day running smoothly—and to prevent any inconvenient crushes. It's not just my ego talking; I've had to let go of three previous assistants because they tried to take things out of the office… and into the bedroom. I even came home one night to find a new hire draped over my office chair.

"Not yet," I say, shaking my head. "But I might need some comfort food soon."

"Fine. I'll grab the chocolates," she sighs, heading off.

I turn back to my phone, tapping my fingers impatiently on the desk. What's the deal? I messaged Chloe nearly twenty minutes ago. She should have read it by now. And replied, taking me up on that dinner invite, and adding a flirty message of her own.

Unless Mia struck out with that opening line.

I turn my phone over in my hand. Mia's good; I only hire the best, and she's never let me down so far, but nobody bats a thousand all the time. Or what if Chloe lost her phone? Or has her notifications muted? Or is at some no-tech retreat for the week…

I stop myself before I can spiral into a vortex of uncertainty.

Why is this so hard? I'm used to my love life coming easy; I don't think I've ever just sat around, waiting for someone to reply.

Maybe I'm overthinking this. I don't need elaborate messages or gifts to make an introduction—I meet women all the time. What's to stop me just running into Chloe in person and saying a casual, "Hey"?

I spring to my feet. "I'm heading out for coffee," I tell Lara, striding out of my office.

"You already had coffee," she gives me a suspicious look.

"Lunch, then. Hold my calls," I say, and then exit quickly before she notices I'm acting like a crazy person.

Or Ethan Griffin circa high school.

I HEAD downtown to Chloe's Pilates studio. I figure I can just drop in and strike up a conversation, but when I reach the building, my feet don't get the memo.

I pace back and forth on the sidewalk outside, trying to get my act together. What the hell is wrong with me? I can see through the front windows; there are a dozen women in class, and normally, I wouldn't hesitate before strolling in and flashing my most charming smile. Hell, being surrounded by beautiful women is just a regular Friday night, as far as I'm concerned, but this is different.

This is Chloe.

Ethan was right. I was hopelessly in love with her in high school—but of course, she didn't even know I was alive. Not like that, anyway. To her, I was just the awkward, tongue-tied guy who stumbled through our study sessions. But even though she was a goddess, even back then, she was still one of the nicest people you would ever find. Sweet, friendly, and totally out of my league. She dated popular jocks and college students: guys who would come pick her up after school in their vintage cars, leaving the rest of us in their dust. I haven't thought about her in years—I figured she was just an embarrassing memory from my dorky past—until I saw her at that bar, and I realized she could be the one I've been waiting for.

And, more importantly, I might actually have a shot at being with her this time around. Because over the past ten years, I've relegated my old awkward high school persona to the trash heap of history. Thanks to a growth spurt, some smart investments, a personal shopper, and the best orthodontist in the city, I'm kind of a catch these days.

At least, according to the city's annual list of most eligible bachelors.

So why am I stuck pacing back and forth outside Chloe's studio, trying to work up the nerve to step inside?

One of the girls at the front desk sends me a friendly smile through the window. Shit. They've seen me. I turn on my heel and bolt to the safety of the smoothie shop across the street. I pull out my phone and give Mia a panicked call. "Where are you?" I demand.

"Just heading home. Why? Did she love the message?" 

"She hasn't answered yet! It's been an hour," I tell her.

Mia just laughs. "Whoa, cowboy. Some people aren't glued to their phones, you know. She's probably still in a session."

"Look, I need to talk to you. Get over here," I tell her, then text the address.

Fifteen minutes later, Mia arrives, toting two massive bags of groceries.

"This better be good," she says, shifting the weight on her hip. "I have ice cream melting here."

I'm distracted for a moment by the tank top clinging to her body and the summery skirt swishing around her bare legs. She looks pretty and fresh—until I get to the impatient scowl on her face. 

"I'm the one who should be complaining," I tell her, shaking it off. "I trusted you to deliver the goods."

"And I did!" she protests. "Tailor-made to capture Chloe's interest. Or her organic cotton bodysuit. Either way, mission: accomplished."

"Then why hasn't she responded?" I ask, holding my phone up. "The message was marked read, so she has to have seen it."

"Unless she doesn't handle her own social media," Mia points out, "or has her notifications muted, or—"

"Shhh!" I fall silent. Chloe has just entered the café, looking radiant in a skin-tight yoga outfit that sends all my blood rushing south. Holy shit, she's gorgeous.

"Cover me," I hiss at Mia, trying to duck behind her, but it's too late. Chloe looks over from ordering with a curious smile on her face.

"Dylan?" she asks, her voice rising. "Dylan Griffin, is that you?"

"Hey." I give her a wave. Damn. I wasn't ready for this. "How's it going?"

"Great!" she beams. "I can't believe this, it must be what, ten years since we've seen each other?"

"Twelve," I blurt. "You look great… I mean, you always looked, you know, but now… uh…"

Mia looks at me like I'm an idiot. Which, to be fair, I'm doing a great impression of one right now.

"I, uh, actually messaged you," I say, trying to pull my act together. "I'd love to get dinner sometime and catch up."

"That was you?" Chloe looks surprised. "Oh, I get so much spam all the time, I figured you were just another creepy guy hitting on me."

"Imagine that," Mia murmurs beside me, clearly trying not to laugh.

I elbow her.

"Nope, all legit and above board," I reassure Chloe, trying my best to look casual. "What do you say? Tonight. For old times' sake."

"How sweet," Chloe smiles. "But I have plans."

"Oh." I try not to feel disappointed. "How about drinks then, tomorrow? Or Friday?"

"Maybe!" she agrees brightly. "I'm slammed right now, but I'll let you know if something opens up. It was great to see you, though."

"You too…" I reply, but she's already sauntering out.

Mia barely waits until the door swings shut before she bursts out laughing. "What was that?" she crows.

"Shut up," I groan. Could that have gone any worse?

"I mean it!" Mia exclaims, looking delighted. "I've never seen you tongue-tied around a woman before!"

"Way to rub it in." I sigh. Clearly, the usual tricks won't work on Chloe… which only makes me more determined. Maybe it's fate, us crossing paths like this. Maybe it's my second chance to show her I'm the man for her.

So I do what I always do when my gut tells me to go for it. I double down.

"I'll pay you fifty thousand dollars if she goes out with me," I announce.

Mia snorts. I hold her gaze and watch realization dawn.

"Wait, you're serious?" Her jaw drops. "Dylan, that's insane!"

"Why?"

"Because I'm not a matchmaker, for starters," she blusters. "Plus, I can't force someone to date you. There are laws against that!"

"You always said the right words can make anyone fall in love. So, prove it," I challenge her, warming to the idea now. A little extra motivation, that's what she needs. "Fifty thousand bucks, to help me win Chloe's heart. Let me know when you've thought up a plan."

And I walk out, leaving her with ice cream dripping down her leg.

Because I'm not a quitter, not anymore. The old high-school Dylan might have slunk off and licked his wounds (and some comfort cookies) in defeat, but I'm not that guy anymore. All I need is a chance to show Chloe that same fact, and she'll see what she's been missing.

And Mia's my secret weapon to make it happen.

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