Chapter 3: First Date Disasters

I changed my outfit four times before Kieran arrived.

The first dress was too formal—like I was trying too hard. The second was too casual—like I didn't care at all. The third made me look like I was playing dress-up in someone else's clothes, and the fourth... well, the fourth ended up on the floor when I spilled foundation on it while doing my makeup.

So naturally, I was back in outfit number two—dark jeans and a soft green sweater—when my buzzer rang at exactly 7 PM.

"Emma? It's Kieran."

His voice through the intercom made my stomach flip. "Coming down!"

I grabbed my jacket and keys, gave myself one last look in the hallway mirror, and immediately regretted it. My hair had that weird half-flat, half-frizzy thing going on, and I was pretty sure I had mascara smudged under my left eye.

Perfect. Because if there was one thing I excelled at, it was looking like a disaster right when it mattered most.

Kieran was waiting by the entrance, hands shoved in the pockets of a dark jacket, looking effortlessly put-together in that way that some people just managed without trying. When he saw me, his expression shifted into something I couldn't quite read.

"Hey," he said, and there was something different in his voice. Softer, maybe. "You look..."

I braced myself for the polite lie.

"Really pretty."

The words hit me somewhere deep in my chest, and I felt heat rise in my cheeks. "Thanks. You clean up pretty well yourself."

It was true. Gone were the paint-stained fingers and rumpled henley, replaced by dark jeans and a black button-down that made his green eyes look almost unfairly intense. He'd made an effort, and that realization made something flutter in my stomach.

"Ready?" he asked.

"As I'll ever be."

We walked in comfortable silence for a few blocks, the evening air crisp but not cold. The city felt different at this hour—less rushed, more alive somehow. String lights hung between buildings, and the warm glow from restaurant windows made everything look like a movie set.

"So where exactly are we going?" I asked, stealing a glance at his profile.

"You'll see." The corner of his mouth quirked up. "Trust me."

"Famous last words."

He laughed, and the sound made my chest warm. "I promise not to take you anywhere that requires advanced motor skills."

"Good, because those are in short supply."

We stopped in front of a small restaurant I'd never noticed before, tucked between a bookstore and a vintage clothing shop. The sign above the door read "Nonna's" in faded gold lettering, and through the windows I could see mismatched tables and chairs, exposed brick walls covered in old photographs, and strings of Edison bulbs casting everything in soft, honey-colored light.

"Italian," Kieran said, as if that explained everything. "The owner is this tiny old woman who will probably try to adopt you within five minutes of meeting you. The food is incredible, and more importantly—" He held the door open for me. "—the floors are sticky enough that even you can't slip."

"How romantic," I said dryly, but I was smiling.

He was right about the owner. Maria Benedetto was maybe four-foot-ten with steel-gray hair piled high on her head and the kind of warmth that made you feel like you'd known her your entire life. She took one look at me and Kieran and immediately launched into what I assumed was Italian, gesturing wildly and beaming like we'd made her entire week.

"She says you're beautiful and I'm lucky," Kieran translated, looking slightly embarrassed. "She also wants to know when we're getting married."

"Tell her to slow down, we haven't even ordered yet," I said, but I was laughing.

Maria seated us at a corner table and disappeared into the kitchen, returning moments later with a bottle of wine and two plates of antipasto that we definitely hadn't ordered.

"She doesn't believe in menus," Kieran explained, pouring wine into both our glasses. "She just feeds you whatever she thinks you need."

"And you're okay with that? Not knowing what's coming?"

Something flickered across his face—there and gone so quickly I almost missed it. "Sometimes the best things are the ones you don't plan for."

I took a sip of wine, studying his expression. "You say that like someone who's learned it the hard way."

"Maybe I have." He met my eyes across the table, and for a moment the air between us felt charged with something I couldn't name. "What about you? Are you a planner, Emma Collins?"

"Recovering planner," I said. "I used to have everything mapped out. College, career, where I'd live, who I'd marry..." I trailed off, thinking of Tyler and the five-year plan he'd had for our relationship that felt more like a business proposal than a love story.

"Used to?"

"Turns out life has other ideas." I gestured around us. "Six months ago, I never would have imagined I'd be here. New city, new job, having dinner with a mysterious artist I met by falling on my face in a coffee shop."

"Mysterious artist?" Kieran raised an eyebrow. "Is that what I am?"

"Aren't you? You teach kids, you paint, you have this whole brooding thing going on..." I waved my hand vaguely in his direction. "Very mysterious."

"I'm really not that interesting."

"I doubt that."

Maria returned with plates of pasta that smelled like heaven and looked like something out of a magazine. She said something else in rapid Italian, patted Kieran's cheek affectionately, and bustled away again.

"What did she say this time?" I asked, twirling linguine around my fork.

"That you have good energy and I should—" He paused, color rising in his cheeks. "—not mess this up."

"Smart woman."

We ate in comfortable silence for a while, the pasta living up to every expectation. I found myself relaxing in a way I hadn't in weeks, the knot of anxiety I'd been carrying in my chest finally starting to loosen.

"So tell me about this job that's been stressing you out," Kieran said, refilling our wine glasses.

I groaned. "Marketing coordinator at Hartwell & Associates. It's... fine. Professional. The kind of job my parents think I should be grateful for."

"But?"

"But I spend most of my day writing copy for corporate websites and pretending to care about quarterly projections." I took another sip of wine, feeling bold. "I wanted to be a writer when I was younger. Like, actually write. Books, stories, things that mattered to people."

"What stopped you?"

The question hit harder than it should have. "Reality, I guess. Bills. Student loans. The voice in my head that sounds suspiciously like my ex-boyfriend telling me I wasn't good enough to make it as a real writer."

Kieran's expression darkened. "Your ex sounds like a real prize."

"Tyler was... practical. He thought my writing was a nice hobby but not something I should actually pursue." I pushed pasta around my plate, suddenly uncomfortable. "He wasn't wrong. I mean, how many people actually make a living writing novels?"

"How many people actually try?"

I looked up at him, startled by the intensity in his voice.

"Sorry," he said, running a hand through his hair. "I just... I hate when people give up on things they love because someone else told them they weren't good enough."

There was something personal in his tone, like he was speaking from experience. "Is that what happened to you?"

"What do you mean?"

"The teaching, the community center classes... it sounds like you're doing the practical thing too, instead of whatever you really want to be doing."

Kieran was quiet for a long moment, staring down at his plate. When he looked up, his expression was carefully neutral. "Sometimes practical is all you get."

Before I could ask what he meant, Maria appeared with dessert—tiramisu that looked like a work of art—and the moment passed. But I filed away the conversation, the way his walls had gone up when I'd pushed too close to something real.

We talked about safer things after that. Books, movies, the weird quirks of city living. Kieran had a dry sense of humor that caught me off guard, and I found myself laughing more than I had in months. By the time we left Nonna's, the wine and good food had left me feeling relaxed and warm, like I was floating slightly above the sidewalk.

"Thank you," I said as we walked slowly back toward my building. "That was... really nice."

"You sound surprised."

"Maybe a little. I haven't had the best track record with dates lately."

"Define 'lately.'"

I thought about Tyler, about our stilted dinners at chain restaurants where he'd spend half the time on his phone and the other half explaining why my career goals were unrealistic. "Ever, actually."

Kieran stopped walking and turned to face me. We were standing under a streetlamp, and the light caught the sharp line of his jaw, the way his dark hair fell across his forehead.

"That's impossible," he said quietly.

"Not impossible. Just... true." I shrugged, trying to play it off. "I'm not exactly the smoothest person to be around."

"Emma." The way he said my name made my stomach flip. "You're..."

He stepped closer, close enough that I could smell his cologne again, could see the flecks of gold in his green eyes. My heart hammered against my ribs as he reached up to tuck a strand of hair behind my ear, his fingers lingering against my cheek.

"You're perfect exactly as you are," he said, his voice rough. "Anyone who can't see that is an idiot."

I couldn't breathe. Couldn't think. Could only stare up at him and wonder how someone I'd known for less than a week could see something in me that I'd never seen in myself.

"Kieran," I whispered, and his name felt like a prayer.

He leaned down, and I thought—hoped—he was going to kiss me. But at the last second, a car horn blared somewhere behind us, and the spell broke. Kieran stepped back, running a hand through his hair, and I wrapped my arms around myself to ward off the sudden cold.

"I should walk you up," he said, his voice carefully controlled.

"Right. Yeah."

We climbed the steps to my building in silence, and when we reached my door, I turned to face him, not sure what to say. How did you end a perfect evening that had ended just short of perfect?

"I had a really good time tonight," I said finally.

"Me too." He was leaning against the doorframe, hands in his pockets again, looking like he was fighting some internal battle. "Emma, I—"

My phone rang, cutting him off. I glanced down at the screen and my stomach dropped.

"Tyler" was calling.

I stared at the phone, frozen. Of all the times for my ex to resurface, this was possibly the worst.

"You should answer it," Kieran said, but his voice had gone cold again.

"No, I—" The ringing stopped, then immediately started again. Tyler had always been persistent when he wanted something.

"Answer it," Kieran repeated, stepping back. "It's obviously important."

And before I could explain, before I could tell him that Tyler was the last person I wanted to talk to right now, Kieran was walking away, leaving me standing alone in my doorway with my phone buzzing insistently in my hand.

I watched him disappear around the corner, then finally answered the call.

"Hello, Tyler."

"Emma! Thank God. Listen, I've been thinking..."

But I wasn't listening. I was staring down the empty street, wondering how a perfect evening had just turned into another disaster, and whether I'd lost something important before I'd even had a chance to figure out what it was.