Chicago: The Stranger on the Train

One train. Two strangers. A night they'll never forget. When a lost wallet leads to a chance encounter.

The train’s wheels screeched against the tracks as it pulled out of the station, and my heart hammered in my chest. My daily commute had become less about getting to work and more about him—the stranger with long dreadlocks who seemed to make time slow down every time he stepped onto the train.

The rhythmic sway of the train did little to ease the dull headache pulsing at my temples, but let’s be honest—it wasn’t the headache keeping me on edge. It was the anticipation. The hope of seeing him again.

“Doors open on the right at Fullerton. Transfer to Purple and Brown Line trains at Fullerton.” The robotic voice crackled overhead.

My eyes scanned the platform as the train slowed to a stop, searching for any sign of him. Nothing. Disappointment sank into my chest as the doors began to slide shut—until a hand shot through the narrowing gap.

It was him.

He slipped inside, settling into his usual seat with an ease that made him seem almost otherworldly. Headphones on, eyes closed, his body moved subtly with the music only he could hear. I let my gaze linger, studying the curve of his jaw, the slope of his shoulders, the way his fitted jeans hugged his thighs.

Almost like he could feel me watching, he adjusted his crotch. My eyes darted—there. The subtle motion drew my focus lower, and I caught my breath, teeth sinking into my bottom lip as my imagination ran wild.

And then his eyes snapped open.

He caught me.

A slow, knowing smirk curled across his lips, his dark eyes locking onto mine. The corner of his mouth twitched upward, an unspoken challenge glinting in his gaze: Keep looking. I dare you.

My phone vibrated in my hand, shattering the moment. Sam’s name lit up on the screen, but whatever he had to say couldn’t possibly hold my attention. My stranger—my stranger—was sitting just a few feet away, and my stop was approaching fast.

Talk to him, I urged myself. Don’t let this moment slip away.

With my heart threatening to beat out of my chest, I gathered my things and crossed the small gap between us. His eyes flicked up, mildly surprised but clearly amused.

“Excuse me… what’s the next stop? I missed the announcement,” I said, my voice wavering slightly.

“Chicago,” he replied smoothly, his lips curling into that lazy, devastating smile.

“Thanks. Still trying to figure my way around.”

He raised an eyebrow. “Really? I’ve seen you on here for months now.”

“Well, I guess I’m not as stealthy as I thought. I just moved here from Georgia.”

“A southern boy in the big city,” he said with a low chuckle and a mock southern drawl.

I smiled shyly. “Yeah, it’s… a change of pace, for sure.”

The train began to slow, the station approaching. My stop. I swallowed hard, the words dancing on the tip of my tongue—Ask him out. Just ask.

But when the moment came, all I managed was, “It was great chatting.”

His smile deepened, his eyes locking with mine. “Likewise. See you tomorrow,” he said, his voice dipped in something suggestive, something electric.

As I stepped onto the platform, I turned back, unable to resist stealing one last glance. He was still watching me, that playful smirk tugging at his lips. I waved, my smile lingering as I turned away, my chest tight.

Tomorrow, I thought. Tomorrow, I won’t chicken out.

My focus was wrecked. The cursor blinked on my screen, waiting for me to care, but my mind was elsewhere—caught in a haze of daydreams that had no place in the middle of a workday.

A loud growl from my stomach pulled me back, sharp and insistent. Right. Food. I reached for my wallet—front pocket, back pocket, jacket pocket. Nothing.

A tight knot of panic coiled in my chest as I searched again. I dropped to my knees, scanning under the desk, flipping through papers, checking drawers. Still nothing.

My heart was pounding by the time I made it to the lobby. Mark, the security guard, leaned against his desk, flipping through his phone.

“Hey, Mark—anyone turn in a brown wallet?” My voice cracked slightly.

He straightened up, gave me a quick once-over, then opened a drawer and pulled out two wallets. He flipped them open, checked the IDs, and shook his head.

“Sorry, Zeddie. Neither of these are yours.”

I exhaled sharply, my hands gripping the edge of the counter. Shit.

Mark offered a faint smile. “I’ll keep an eye out.”

“Thanks,” I muttered, already turning back toward the elevator.

As the doors closed around me, I leaned my head against the cool metal wall and let out a slow breath. My stomach growled again, louder this time.

Wallet gone. Hunger gnawing at me. Mind still tangled in those damn daydreams.

Perfect. Just perfect.

Eager to leave work early, I dashed home. I searched every nook and cranny of my apartment, my eyes darting around the room in desperation. I slumped down on the couch, defeated, and poured myself a drink. Just then, an unexpected knock at the door jolted me.

I peered through the peephole to find the last person I expected to see.

“Just a minute,” I called out, quickly checking myself in the mirror and freshening up. 

I licked my finger and slicked down my eyebrows, checking my teeth and quickly swishing some mouthwash.

When I opened the door, there he stood, the mystery man from the train, with my wallet in hand. I was grateful but also a little confused.