Chapter 2: Heels, Hazards, and a Cucumber Crisis

It was late March, and Manhattan was buzzing—neon everywhere, money everywhere. Nights in the city felt like they were on a permanent sugar high.

Yellow cabs sped by, horns blaring. The air was sharp with roasted nuts from a street cart and the tang of spring rain on concrete. It felt like every window in every skyscraper was a spotlight, aimed right at me.

I stood outside a luxury store on Fifth Avenue, checking out the ‘young man’ reflected back at me—black hoodie, jeans, sneakers. Nothing about this thrift-store look screamed ‘gaming god.’

The mannequins behind the glass were rocking tuxes that probably cost more than my rent, but I held my ground, chin up. I was playing a part, and I’d learned ages ago that confidence was the best disguise.

Luckily, my face was my moneymaker. With these looks, I could show up in pajamas and nobody would care. Plus, I was naturally tall—5’9” as a girl, then two-inch insoles and another inch from lifts. I could pass for six feet, easy.

I practiced standing with my shoulders back, hands in my pockets, like those college guys who want to look chill but in control. I told myself: you belong here. Even if my knees were shaking like crazy under my jeans.

Even so, I kept my face as steady as a male model, but inside, my nerves were doing jumping jacks. Online, faking a guy’s voice was one thing, but in real life… Could I really pull this off?

I sucked in a breath, feeling my heart pound against my ribs. I’d watched enough teen dramas to know how guys moved, joked, slouched. But would that be enough?

I mean, she was a Manhattan heiress—sharp as hell. What if she saw through me and called me out? That $15,000… and the promised hundred grand…

I pictured my bank account, the negative balance flashing like a dare. This was my shot, and I couldn’t let it slip by.

Whatever. I’d just bet everything on this one shot. All in.

Right now, I was fidgeting with the cucumber I’d tied around my waist for the third time. God, this was ridiculous.

Yeah, a cucumber. Last-minute prop, thanks to the bodega downstairs. The things I do for a paycheck.

“Ash Carter?”

A voice behind me—softer and sweeter than it’d ever sounded over the headset.

Everything just stopped for a second. My body went stiff, fingers twitching away from the cucumber as I turned around, trying to look as chill as possible.

There she was—a woman with long, ink-black hair loosely pinned up, a few wisps falling along her slender neck. I took in her Oscar de la Renta dress, Gucci belt, Tiffany clover bracelet, and Louboutin heels in about two seconds flat.

She looked like she’d just stepped out of a Vogue spread—effortless, untouchable, and with a hint of danger. Her perfume drifted over, light and expensive. I swear, my mind went blank, like someone pulled the plug.

Charlotte Harrington hesitated, her gaze lingering on me. “You… look different from your photos.”

My heart almost stopped right there.

I swallowed, suddenly hyper-aware of every detail. Was my voice too high? Was my jawline sharp enough? I forced myself to meet her eyes, hoping she couldn’t see through me.

A flush crept up her fair cheeks. “You’re even more handsome in person.”

Okay, can we not recycle those cringey internet pickup lines? Please and thanks.

I pressed my lips together and looked down. “Thanks.”

I shoved my hands deeper into my pockets, playing the shy-but-cool boyfriend. Say less, let the mystery do the work.

“Ahem, I reserved a spot at The Violet Hour. My friends are all waiting.” Charlotte reached out her hand, pearly nails glinting under the neon. “Shall we?”

I noticed how stiff her gesture was. After a pause, I didn’t take her hand. “Sure.”

Instead, I gave her a little nod—like I’d seen in indie films—and kept my hands to myself. No way was I risking the cucumber situation this early in the night.

Seeing me keep my distance, Charlotte actually relaxed a bit, letting out a light laugh. “You’re just as chill as you are online.”

Her laugh was soft, a little breathy, and I caught the way her shoulders dropped, tension draining away. Maybe I was pulling this off after all.

I kept my mouth shut, just slowing my pace to match her heels.

I watched the way she navigated the sidewalk, every step measured and elegant. I matched her stride, careful not to outpace her. The city noise faded, replaced by the low buzz of anticipation.

So… did that mean I’d passed the first test?

I shot her a sideways glance, catching the little smile tugging at her lips. Maybe I wasn’t the only one faking it tonight.

But this was just the warm-up.

Soon we hit the bar. Even the way you got inside was fancier than anything I’d seen. Inside, the lights were low, jazz floated in the air, and the sound of ice clinking in glasses was just right.

A velvet rope, a nod from the doorman, and suddenly we were in a world of leather booths and gold-rimmed glasses. I took it all in, trying not to look like a tourist.

“Char!”

A few stylish young people were gathered at the central booth. As soon as Charlotte walked in, they waved her over.

Their laughter echoed, turning heads. I straightened my jacket, squared my shoulders, and followed her into the lion’s den.

“Whoa, this is the online boyfriend you told us about?”

A short-haired girl gave me the once-over, her eyes lighting up again and again.

She checked me out like she was picking out a new car. I forced a lazy grin, the kind that said I was used to this—even if my palms were sweating.

“He’s so good-looking! Pretty enough to be a girl! Char, you really know how to keep your little darling hidden!”

—Pretty enough to be a girl.

That one hit me in the gut. I pressed my tongue to the roof of my mouth, keeping my face cool.

I let out a slow breath, counting to three. Years of practice made it easy to take a punch—verbal or otherwise.

Charlotte, clearly embarrassed by her friend, said, “Maddie, knock it off.”

She turned to introduce me, voice soft. “Ash, this is Madison Reed, my best friend. That’s Carter Reed, her brother. And that’s…”

I quietly filed away the names, nodding here and there. I also clocked the red-haired Carter—he’d been staring at me since I walked in, with a look that screamed ‘I don’t trust you.’

His eyes were sharp, like someone who’d spent his life in private schools and didn’t trust outsiders. Noted. I’d keep my guard up.

“I heard you’re still in school,” he asked. “Which college?”

“Lakeview College,” I said, making up a school from my hometown.

I tossed it out there with just enough boredom to sound real, hoping he’d drop it.

“Never heard of it,” Carter shot back. “Wait, is that, like, a community college or something?”

His tone dripped with skepticism, but I just let it roll off. Guys like Carter loved making people squirm.

I didn’t react or look annoyed. Charlotte bit her lip a little, looking apologetic.

She shot me a quick, sorry-about-him glance.

Maddie smacked her brother. “Enough, Carter! Not everyone goes to Columbia like you.”

She rolled her eyes so hard I thought they might get stuck. The tension eased up a notch.

Thank God, the server arrived with drinks, cutting the awkwardness.

The server, crisp in white, set down a tray of cocktails and sparkling waters. The clink of glass was music to my ears.

Charlotte handed me a glass, keeping a sparkling water for herself. "Ash, this is their signature drink. Try it."

She held it out with both hands, her nails catching the light. I took it, letting our fingers brush for a second—just enough to sell the story.

I took a sip. It burned way more than beer, and it wasn’t even sweet. Not my thing.

I forced a smile, swallowing the fire. I’d had worse in college, but not by much.

“So, how did you two meet?” Maddie leaned forward, eyes sparkling, ready for gossip.

Her curiosity was practically vibrating. I braced myself.

"Ahem… I booked Ash as my paid gaming partner," Charlotte smiled, her fingers resting on my wrist. "He’s really skilled and a great person. We just got to know each other over time."

Her cool fingertips pressed against my skin—she was clearly nervous about lying.

Her grip was tighter than I expected, so I gave her a quick squeeze under the table. Teamwork.

"Paid gaming partner?" Carter scoffed, tapping his glass. "Char, since when do you play video games?"

He looked at her like she’d just said she played D&D on weekends.

“What’s wrong with that?” Charlotte kept her tone gentle, but I heard the edge.

She straightened up, chin lifted, not about to be embarrassed.

Carter shrugged. “Nothing, I just think you’ve changed. Ever since that thing with Ben Sinclair…”

Charlotte’s face went still, like she’d been hit with a bucket of ice. “I don’t want to talk about that.”

A heavy silence dropped over the table. Even the jazz faded into the background.

“…Sorry.” Carter raised his hands, then shot me a glare. “I’m just worried you’ll get played by some jerk.”

He said it like a warning, but I just smiled, letting it bounce right off.

Ice melted in my glass. I looked from the ice up to Carter’s face, and out of Charlotte’s line of sight, I shot him a little smirk.

I tilted my head, daring him to say more. If he wanted a fight, he’d have to try harder.

Carter was stunned, then almost flipped the table. “What are you smiling at?!”

His voice cracked, drawing a few looks from nearby tables. I almost laughed.

Maddie lost it. “Bro, why are you so jumpy tonight? If you hadn’t sworn you weren’t into Char, I’d think you were jealous.”

She waggled her eyebrows, loving the drama.

“You guys didn’t see it!” Carter jumped up, pointing at me. “He’s just a fake nice guy!”

His outburst echoed, but I kept my face blank, letting Charlotte take the lead.

Charlotte looked at me, searching for reassurance.

I’d already pulled it together, tilting my head with innocent confusion. “What?”

I let my voice go soft, almost bored, like I was missing the joke.

“Damn! He’s acting!” Carter was so mad his teeth were gritted. “Char, you can’t be with someone like this—”

“Enough!” Charlotte raised her voice for the first time. “This is my choice, Carter. I hope you’ll respect that.”

Her words were sharp and clear, and for a second, everyone at the table went silent.

Carter’s jaw dropped. In the end, he slumped back, grabbed his drink, and downed it in one go.

He glared at his glass like it had personally insulted him. I almost felt bad for him—almost.

"Jeez, bro, take it easy. You can’t even hold your liquor…" Maddie teased.

She snatched his glass away before he could grab another. The whole scene would’ve been funny if it weren’t so tense.

Right then, I felt the cucumber at my waist start to slip. I quickly shifted my posture, trying to stop disaster.

My heart skipped. I pressed my elbow against my side, praying no one noticed.

But it was too late. The cucumber was sliding down my leg, the cloth strap totally shot. Why did I have to go cheap?

I could feel it inching lower—a disaster in slow motion. Why do I do this to myself?

Noticing my frown, Maddie asked, “You okay? Not feeling well? These drinks can be rough for newbies.”

She leaned in, concern creasing her brow. I forced a smile, trying not to look panicked.

“I’m fine,” I said, then turned to Charlotte. “Where’s the restroom?”

I was already half out of my seat, desperate for an escape.

“I’ll take you,” Charlotte offered, starting to get up.

Her voice was gentle, but I couldn’t risk it.

“No need, just point me there.” I cut her off, not wanting to risk more awkward angles.

I kept my tone casual, even as I clamped a hand over my waistband.

“Over there! Out the door, right at the end,” Maddie said, pointing.

She gave me a thumbs-up, totally clueless about my crisis.

I nodded, stood up as naturally as possible, one hand pressed at my waist as I headed for the restroom.

Every step felt like a mile, but I forced myself to walk slow. Just another guy going to the bathroom, nothing to see here.

Hurry, hurry, hurry.

My mind was racing, running through every possible disaster. If that cucumber hit the floor, I’d never live it down.

And then it hit me—should I use the men’s or women’s room?

I hesitated, checked myself in the mirror—yeah, still looked like a dude—and went for the men’s room.

My heart pounded as I checked the stalls—empty. Thank God.

I let out a breath, feeling the cucumber’s strap finally give out. I grabbed my waistband with both hands and ducked into a stall.

I fumbled with the belt, yanking the cucumber back into place, cursing under my breath. This was not the glamorous life I’d pictured.

But just as I opened the stall door, the main door banged open.

Carter strode in, trailing a faint smell of whiskey. “Hey.”

His footsteps echoed, sharp and purposeful. I froze, caught like a deer in headlights.

I froze for a second, then kept moving into the stall, reaching for the lock.

I tried to disappear, but Carter wasn’t having it.

But Carter grabbed my arm from behind. “Hey! I’m talking to you, don’t play dumb.”

His grip was tight, fingers digging into my jacket. I spun around, trying to look annoyed instead of terrified.

“What do you want?” I stiffened, one hand gripping my waistband.

Crap, crap—the cucumber was sliding down my thigh, about to drop out my pant leg.

I clenched my teeth, praying for a miracle.

Carter sneered. “Charlotte’s family is loaded—way more than you could ever imagine. Got it?”

He leaned in, eyes narrowed. The whiskey on his breath was sharp and bitter.

“…Got it. Can you let go of me now?” My voice was tight.

I tried to sound bored, but my heart was pounding so loud I was sure he could hear it.

“You don’t get it. Char’s never dated before, she’s really naive. She’s been through some stuff lately, that’s why she’s acting out. So if you’re just after her money, you’d better quit while you’re ahead.”

He was playing the big brother, but all I heard was a challenge.

“That’s between me and her.” I snapped, yanking free. “I need to use the bathroom. Can you stop blocking the door like a creep?”

I glared at him, daring him to push me. My hand was still pressed to my side, holding everything together.

That set Carter off again, and he gripped my wrist so hard his nails dug into my skin.

He yanked me around, way too close. “Damn it! You’re just a pretty-faced small-town kid, what are you so cocky for?!”

He yanked me to face him, close enough to feel each other’s breath. “You—”

Right then, the cucumber finally gave up, sliding down my pant leg with a rustle.

It landed with a soft thud, and for a split second, we both stared at it in horror.

Carter’s eyes dropped, spotting the suspicious bulge. His face went blank. “Your…”

His mouth opened and closed, stuck between laughing and screaming.

In a panic, I just yanked the cucumber out of my pant leg and smacked him on the head with it. “Get lost, you creep!”

I tossed the cucumber in the trash and slammed the stall door behind me. My cheeks were on fire, but at least I’d survived—barely.

By the time I washed up and got back to the booth, Charlotte was chatting with Maddie. But she was clearly distracted, her hazel eyes flicking to the door like she was waiting for someone—probably that Ben Sinclair guy.

She looked up as I approached, her smile a little too bright, fingers twisting her napkin. I wondered if she was regretting this whole charade.

When she saw me, she looked startled, like she’d almost forgotten about her ‘boyfriend.’ She quickly pulled her gaze back and forced a slightly stiff smile. “Ash, you’re back. Everything okay?”

Her voice was gentle, but her eyes searched mine, looking for reassurance.

I shook my head.

I kept my expression blank, not wanting to worry her. The less said, the better. Ha.

Maddie looked behind me. “Where’s my brother? He didn’t bother you, did he? He insisted on going to the bathroom after you left—I couldn’t exactly tie him to his seat…”

She gave me a sheepish grin, like she half-expected me to say something wild.

I shook my head again.

I shrugged, playing it cool. No way was I bringing up the cucumber incident.

Maddie sighed. “He’s not a bad guy, really. He’s always treated Char like a little sister—he’s just way too protective.”

She rolled her eyes, but there was real affection in her voice.

“Ash, did Carter say anything to you?” Charlotte asked, her gaze flickering.

She looked worried, biting her lip, waiting for my answer.

“Not much.” I sat down beside her. “Just guy talk.”

I leaned back, arm draped over the back of the booth, looking as casual as I could.

Before Charlotte could get more anxious, I added, “But he drank too much. When I left, he was still hunched over the toilet. Hope he’s okay.”

I shot her a reassuring smile, hoping she’d let it go.

—Hope that after getting clocked by my cucumber, he sleeps like a baby and wakes up fine.

I bit back a grin, picturing Carter’s face as he came to. He’d never live this down.

Hearing this, Charlotte and Maddie exchanged surprised looks.

They both raised their eyebrows, but didn’t push. Maybe they sensed there was more to the story.

Maddie covered her face, clearly embarrassed for her brother. “Told you! He can’t hold his liquor, but still tries to show off. I’ll go check on him—make sure he doesn’t drown in the toilet or I’ll be an only child.”

She grabbed another guy for backup, winking at Charlotte on her way out. "The night’s still young—enjoy your couple time."

Her sing-song voice lingered, and I caught the blush creeping up Charlotte’s cheeks.

Blushing at the hint, Charlotte seemed at a loss for words and handed me another drink. This one was blue and pretty.

She pushed the glass toward me, her fingers brushing mine. The drink sparkled in the low light, promising a sugar rush and a headache.

She picked up her sparkling water, clinking it gently against my glass. "Ash, thanks for coming to meet me."

Her voice was soft, almost shy. I lifted my glass, clinking back with a little smile.

I took a sip of the blue drink—cold and sweet, way better than the last one.

The sugar hit my tongue, washing away the taste of nerves. I let out a quiet sigh of relief.

“No need to thank me.” I couldn’t help another sip before adding, “I’m just here for the money.”

I said it with a wink, trying to lighten the mood. But the words just kind of hung there, heavier than I meant.

Charlotte looked surprised by how blunt I was. The blush faded a little, her smile wobbled. Then her gaze shot past my shoulder, fixing on something in the distance.

Her eyes went wide, and I followed her gaze, bracing for whatever was coming next.

Her face changed in an instant, tensing up like she’d been hit with a cold wave.

She straightened in her seat, hands twisting in her lap. I could see the storm brewing in her eyes.