The Valentine’s Bet

1. Chapter One

Chapter One

Amy

Alone ... the day after Christmas.

I stare out the tiny window of my New York City apartment overlooking Central Park. Moving to the Big Apple is a dream come true—I should feel grateful.

And I do.

Mostly.

But the fact that I booked my flight the morning after Christmas has me questioning my life decisions. Because I don’t start my new marketing job until Monday, and I have zero friends here in New York. While the whole world is abuzz with the lingering holiday vibes, I’m stuck in my apartment.

Alone.

Mom was right, I should’ve just stayed in Chicago another day .

I flop back on my bed—which is right in the middle of the living room, kitchen, and dining area. I’m realizing now that I didn’t appreciate the two-bedroom apartment I had back in Chicago nearly enough.

“At least the bathroom is private,” I mumble to myself, staring up at the light overhead. “Ugh.” I groan and roll over, reaching for my phone. While I’m not usually one to wallow in self-pity, I know that if I call my mom, she’ll just remind me of what I already know—that I didn’t have to come back so early—and I’m not really in the mood for that. I only moved into this apartment a week before Christmas. I wanted time to get settled in ... or so I thought.

I scroll through my contacts until I land on Eliza’s name.

My best friend will listen to me.

She always does.

I put the phone to my ear, hoping she’s not too busy with her new husband.

“Hey you,” she greets me, her tone as bright as the Christmas lights still dangling on the little Christmas tree I set up in the corner before I flew home. “How’s New York?”

“It’s, um—” I pause, running my tongue along my lip. “Lonely.”

“Aww, I’m sorry. I’m sure it’ll get better once you get settled and make friends.” She’s always encouraging, but the laughter I hear in the background sends a pang of jealousy through my body. “I can definitely relate to how you’re feeling, though,” she adds. “When I first moved from Chicago to West Falls, I didn’t know a soul apart from Granny. ”

“But then you met Nick the day you moved there.” I sigh.

“Yeah, but only because he had to rescue me after I fell through that decrepit wooden access ramp, which was pretty much the most embarrassing moment of my life.”

“And then you married him.” I chuckle, twirling some of my chocolate-colored hair between my fingers. “Ugh, you’re so lucky. You have the cutest love story in the entire universe, and I’m sitting here alone at twenty-nine—having never even kissed a guy . ” I facepalm myself.

Eliza is pretty much the only person, other than my mom, who knows that I’m that freaking lame. And I don’t even really have a good reason for it. I’ve just been so focused on building my career that, up until this point, I didn’t really make time for dating (or kissing). I guess, in the back of my mind, I always assumed it would just happen for me, that I’d stumble upon Mr. Right in a grocery store or the library or something.

But now that I’ve officially made it—having landed my dream job as a marketing executive for a prestigious firm in the heart of Manhattan—I’m finally ready to start getting serious about finding someone to share my life with.

“You know, you’re in that huge city now. You could very well have your first kiss by New Year’s Eve,” Eliza says. “You just have to get out there and be bold—we both know you can do that. You’re seriously the only person I’ve ever met who never meets a stranger. You’re so bubbly and outgoing—I think you could probably have a conversation with a wall.”

And I’ve had plenty, thanks.

“Brick is the best listener,” I quip.

She bursts into laughter. “See, you’re hilarious, Amy. There’s hope for you.”

I sigh, my eyes drifting to my closet. I completely revamped my wardrobe before moving here, trying to match the NYC look. It’s not all that different from Chicago, but it feels that way... And maybe, somehow, new clothes will attract a man.

“Amy, you’re gonna be just fine, and you’re going to find love. I know it.” Eliza could be on one of those pep talk reels that play on my Instagram feed.

My gaze drops to the floor. “It’s just that ... well, I’ve kinda started to wonder if there’s something wrong with me.”

“There’s nothing wrong with you.” Eliza counters my negativity, which is just as annoying as it is helpful. I know the truth, but ugh , something about being all alone the day after Christmas makes me feel like wallowing right now. “You’re one of the best people I know. You just need to suck it up, search the internet, and find something fun to do this evening. Put yourself out there!”

I glance over at the tiny clock hanging on the wall and squint. “But it’s already six-thirty. And I don’t even know where to go.”

“Well, I can tell you one thing. Don’t go into Central Park alone after dark. That’s not a good idea.”

I snort. “We lived in Chicago. I think I can handle myself. I’m not worried about getting mugged. I’ve done my homework. Plus, you know I’ve got that pepper spray on my keychain. ”

She laughs. “Maybe you should see if there’s some type of local singles get-together tonight. They used to have meet-ups at the Crooked Lagoon back in Chicago. I know a few people that went to them.”

“Do you really think I could meet the one at something like that?”

“Girl, I fell through a rotten ramp and met the one. I think your odds are much higher than mine were. It’s not like you’re going on Tinder or something. Most people who go to those types of events want to find the right person.”

“Or they just want to hook up,” I say, my lips turning downward.

“Maybe,” Eliza hums. “But you can usually spot those people. They’ll make flirty advances and want to leave early.”

“Yeah, okay.” I make a mental note. “I’ll steer clear of men who make any flirty advances or offers to leave early.”

“Maybe just be ... cautious. Not every person who flirts or leaves early is a red flag. Some men might be flirting with you because they genuinely like you—and they might want to leave early if the event runs too late.”

I raise a brow. “This is contradictory.”

“You just have to feel them out,” Eliza says. “You can do it. Just read their body language and whatnot. Of course, I thought I was reading Nick correctly and it was all wrong. He was in love with me while I thought we were just friends.”

“I think deep down you knew,” I reason, my heart fluttering at the thought of finding that kind of love for myself. “And it’s so romantic. I wish I had that kind of story.”

“Your story is just beginning! And I bet it’s gonna be epic, considering you just moved to one of the greatest cities ever. You have so many opportunities. Starting now. Go find that singles night! There’s bound to be one,” she says with an audible smile. “There’s plenty of people in the city who probably feel just like you do.”

“True,” I say, putting her on speaker and opening Google. “Do you think I should just try to find the closest one? Or one that looks the most promising?”

“Probably the closest—unless the most promising one isn’t much farther away. Start slow tonight.”

I nod in agreement. “Okay.” I look over the page, scanning the events that are popping up. “ Millionaire Singles Mingle ,” I read aloud, frowning. “I definitely do not fit into that category.”

“You could go anyway.” Eliza laughs. “Fake it till you make it, am I right? I bet it would be a real hoot.”

“Yeah, I think I’ll pass. The moment I walk in the door wearing my twenty-dollar sweater, they’d probably make me leave.”

“But maybe you’d catch the eye of a handsome, rich man before they kick you out,” Eliza coos before giggling. “That would be totally wild.”

I perk up. “So should I go?”

“What else is there?”

“Let’s see. There’s a speed-dating event a couple blocks from me. I mean, it looks like it might be fun. I’ve never speed-dated before. ”

“Isn’t that where you just switch partners after, like, five minutes of talking? That could be fun—and you’d have a chance to meet a lot of people, too.”

“Okay,” I say, sitting up. “I’m going. It starts at eight. That’s plenty of time for me to get ready.”

“Yay! This is gonna be great. And you know how to be New York-pretty.”

“I have no idea what that means, but absolutely. Yes. I’ll look all business.”

“But fun.”

“Yeah, business and fun.”

Eliza giggles. “You’re so cute. But seriously, dress like the hottie you are. I’m literally so excited for you. I can’t wait to hear all about it.”

“I wish I could just FaceTime you through the whole thing.”

“You got this,” she encourages. “Go get ’em, Amy. Just be the bright light that you are and show those New York guys what they’re missing out on. Oh, and make sure you tell me everything after it’s over—and please let me know when you make it back to your apartment safe. You know the drill.”

“Yes, ma’am,” I say, saluting though she can’t see. “I’ll text you during the event if things get dicey.”

“Deal. Take pictures of the place, too. I love the NYC vibe. It’s so amazing.”

“Okay, okay.” I stand to my feet and head for the bathroom. I have no idea what I’m going to wear, but there’s bound to be something promising in the pile of new clothes that my mom and I bought the weekend I moved in. “Have a good night and tell Nick and the rest of the fam that I said hi—all that good stuff.”

“I will,” she chimes. “Love ya.”

“Love you, too,” I say before hanging up.

Phew. Eliza’s right .

I do have a lot to offer.

And it’s about time I shake off the holiday blues and put myself out there.

A smile spreads across my face as I look in the mirror. Even with all the holiday eating I partook in, my complexion is on point . I run my fingers through my dark waves, wondering if I should wash and attempt to tame the beast of curls or work with what I have.

So many decisions.

My stomach flips as I start the shower. A fresh city deserves a fresh me. My cheeks flush as I step under the warm water, imagining what might become of tonight. Maybe I’ll be walking out with a second date...

Maybe I’ll experience love at first sight.

Wouldn’t that be something?

I imagine myself calling up Eliza tomorrow, telling her all about some dreamy, dark-haired, handsome stranger with eyes that see right to my soul. My heart thuds in my chest at the thought of that first kiss...

And all the things that might follow .

Roses, date nights, parties, and movie nights in. I want it all so much I can hardly stand it.

So tonight, I’m going to put my best foot forward and give it my all.

Why not try to get my first kiss by New Year’s? What do I have to lose?

I reach for my phone and turn on “Welcome to New York” by Taylor Swift. Her voice fills the bathroom and I sing along, feeling lighter than ever.

Tonight is going to be special.

I just know it.