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Meeting On A Train

By Damon Yeargain

Illustration by Yibeni Tungoe

               Top Ramen. That’s what I had for breakfast this morning (and for dinner last night.) I did have mac-n-cheese for lunch yesterday, so I guess I’m a poster child for culinary diversity.

               Become an entrepreneur. Live in debt. Worry constantly whether you’ll be thrown out on the street come the first of the month. And if you do manage to succeed—congratulations—you’re now a greedy capitalist.

               But hey, it’s a terrific weight loss program. With billions wasted on failed diets, maybe I should be marketing that in lieu of my software.

               Stop it. I run my finger across one of the straps on my laptop bag. You can’t afford to go down this path.

               I step up to the ticket kiosk for the BART—the Bay Area’s Rapid Transit system—and turn to see an attractive blond two kiosks down. Smiling.

               At me.

               I snap my head back to the ticket machine. Was she really looking at me?

               While my card cycles through the approval process I slowly glance back over, trying to only move my eyes so as not to be obvious that I’m looking at her. She is purchasing her ticket. There is a hint of a demure smile on her face.

               Probably smiling at someone else, I think, trying to push away the thought as I grab my ticket. Of course, it’s 10 AM on a Tuesday with hardly a soul around. I look back over but she’s gone. ‘Damn’ I mutter, but it’s a lie. What I feel isn’t disappointment, but relief. I’ve been saved from the grief of trying to strike up a conversation with her—and blowing it.

               As I walk to the train, I wonder if I’d been staring at her. I have a habit of getting lost in my head and staring at something. Or someone. Often an attractive someone.

               I position myself on one of the black rectangles that indicate where the train doors will line up. It’s warm and I contemplate taking off my suit coat but decide against it. The train is often chilly, and my coat is less likely to get wrinkled if I keep it on.

               I think of the woman at the kiosk again. Of her smile. Her blond hair with a slight wave in it.

               Stop it. Stay focused.

               I mentally go through my slides. Once on the train, I’ll pull out my laptop and open PowerPoint. It’s a moot point though. I have memorized the presentation and could probably recite it in my sleep. The problem isn’t that I don’t know the material, it’s that I turn into the Amazing Captain Studder once in front of an audience.

               She has those braces that are meant to be clear but don’t really hide the fact that she’s wearing them. I know this because she is standing on the rectangle next to mine. Smiling. She is looking straight ahead, but I’m pretty sure she’s glancing at me peripherally.

               Oh, listen to yourself. That square is a good fifteen feet away from you. She is probably just thinking of something else that is making her smile. You do that all the time. And what does it matter anyway? You’re broke. Where would you take her? And let’s not forget you have a very important meeting in less than an hour. You’ve blown so many pitches you’re going to have to start responding to emails from Nigerian princes to get funding.

               When the train stops, I find an empty seat, which isn’t hard to do because it’s nearly empty. I pull out my laptop.

               “Is this seat taken?”

               It’s her! My hotty in braces. “Please,” I answer, gesturing for her to take the seat. 

               Her outfit is simple: white blouse, black skirt, heels. Nothing meant to stand out—and yet, I can’t take my eyes off her. What I notice most is her smile. Why do some women look good in braces?

               “What’s on the slides?” She asks. She must have seen them as she walked up.

               “Just my entire life,” I say more sharply than I mean to.

               “I’m sorry,” she responds. “I’ll leave you alone if you want.”

               “No, no. That didn’t come across the way I intended,” I close the lid on the laptop. “Just hoping not to blow my pitch today.”

               “Aw…Why do you say that?”

               I tell her that it’s because I’ve blown a million already. She looks at me sympathetically without saying anything. Her eyes encourage me though. I explain a little about my business idea. It sounds absurdly silly as I describe it, but she gives me the ‘please continue’ look.

               For someone who usually struggles to talk to strangers, I suddenly can’t stop. I even tell her about how I get so nervous during presentations that I have trouble answering even the most rudimentary questions.

               “You know,” she says. “I’m pretty good at this sort of thing. Want to practice on me?” 

               “I guess…are you sure I haven’t bored you enough?”

               “I’m not easily bored.” Her voice sounds like a wink.

               I shrug my shoulders. The first few slides are an overview of what I’ve already told her, but since I’m practicing: “From first-hand experience I know there are tons of independent computer technicians with nowhere to turn for support. Solutions4Techs, my company, is going to fill that void. We have this software…”

               She interrupts to ask if I’ve started development. I nod. Then she asks if a demo of the software is part of my presentation. Another nod.

               “Might I suggest skipping most of the intro and jumping to the demo?”

               That’s actually good advice. She seems to know her stuff. I’m about to follow her suggestion, but my neck’s sore from twisting sideways in my chair so she could see the computer screen. Without thinking about it, I hop into the open seat next to her.

               “See you just double-click,” I say. “No installation required. Or you can logon to a portal on my website.” A trace of her perfume hits me. We are sitting so close I can actually feel the warmth of her body.

               Energized, I continue. “That’s not all. It keeps track of everything you do.” I try to focus on the screen, but my eyes keep drifting toward her bare legs.

                She asks if I have sold any of the software.

                “A few copies,” I answer, my voice jumping an octave higher than normal. “Sales isn’t exactly my strongest suit.”

               She crinkles her eyes as if it was a puzzle she was trying to solve. She asks how I pay the bills.

               The demo’s essentially over, so I close the laptop lid, and reach for its bag. I can’t quite reach it, so I jump back to my original seat across from her. I feel the back of my neck perspire as I pack the computer away. Her questions, even if unintentional, were starting to sound like interview questions.

               I tell her I wasn’t doing much in the way of employment. “I’ve had a few IT gigs here-and-there,” I say. “The problem is that I see stuff that can be better. Like, employees doing the same manual tasks over and over. I can’t help myself. They don’t know how to automate, so I do it for them. Then I find ten other tasks just like it. Next thing I know I’m working twelve-hour days with no time to devote to my business.”

               “Have you thought about a job outside of IT?” She laughs.

               “I did,” I respond. “I had a job as a bus driver for one of the off-airport parking lots.”

               “On my very first pick-up, there was an elderly woman struggling with her bags. She didn’t speak English, and I couldn’t understand her—just that she kept waving me off.”

               “Eventually, I realize she was trying to tell me she couldn’t afford a tip. So, I grabbed one of her bags and pulled it onto the bus. It was absurdly heavy—and she had four of them. She must have spent her last peso on overweight charges.”

               “Funny thing was, while she didn’t tip—everyone else on the bus did. A lot. I thought I’d stumbled onto the best kept employment secret of all-time. It wasn’t until the next runs, where nothing eventful happened, and the tips dropped-off, that I figured it out.”

               I glance at her while I am speaking. Her encouraging nods draw the words out of me.

               “That gave me an idea, “I continue. “I started putting small bottles of water and soda in a cooler out for people. Eventually, I got an espresso machine.”

               “What?” She smiles. “How on earth did you mount it?”

               “Very carefully!” We both laugh.

               “Seriously, I got a couple of single-shot machines. They’re small and don’t need to be mounted. I’d brew between stops.”

               I was about to move my foot but stopped when I realized that one slight shift and I’d be brushing the edge of her toes. Had our feet been slowly inching toward each other?

               “It’s funny,” I continue. “Many of the other drivers were so focused on the bad tips they got, they never realized how much was within their control.”

               “Sounds like you need to follow your own advice.”

               “What do you mean?” I ask.

               “I mean, maybe don’t focus on the bad pitches you gave,” she says. “Allow your enthusiasm and hard work to show.”

Illustration by Yibeni Tungoe

               She had been playing with her necklace, slowly pulling the gold chain back and forth. Watching it trace the soft fragility of her neck, I noticed her hair again. It wasn’t overly styled. Just a soft wave, like it dried that way, naturally, on its own. Almost everything about her carried a muted, understated quality: pretty without trying to be, confident without drawing attention to herself; smart, business savvy. Then there was that smile, her braces…

               “Finish telling me the story,” she brings me back to the moment.

               “Where was I? Oh yeah, I started bringing drinks…”

               “And an espresso machine…” she teases.

               “RIght. I got such enthusiastic compliments from my riders that within six months of me starting that job I was training the other drivers.”

               “Let me guess,” she smirked. “You were working twelve hour days again.”

               “Pretty close. I quit the day I found myself painting the sign out in front of the parking lot.”

               “No!” She laughs covering her mouth. 

               “Oh yes. In my defense, it was old and faded. Clearly a deterrent for people wanting to park there.”

               “So, you do know something about marketing,” she says playfully, reaching her hand towards my leg but stopping short.

               “Sure.” I roll my eyes. “The blatantly obvious I know.”

               “Hold on a second,” she says, and starts vigorously typing on her phone.

               I wait. She keeps typing, her expression focused—decisive.

               The train begins to slow. The next stop is mine. I cough to get her attention. She responds by holding up her hand as if to suggest I wait a little longer.

               I stand there. Unable to move. Unable to speak. Tell her you have to go. Better yet, tell her you have to go while asking her for her phone number.

                People shuffle off the train. Passengers trickle on. Ask her for her Linked-In account. Why the hell is she still typing?

               The driver makes an announcement. I can’t understand it, but I assume thetrain is going to start moving at any moment. Pretend you’re leaving. Do something…Anything. But my feet are lodged in concrete.

               In the midst of my internal war, she finally looks up. She hands me her phone. I look at her. Confused.

               “Take a look at the text I just wrote.” An eternity had already passed since the train stopped, but she gives a gesture that says: ‘just do it.’

               As I look at her phone the driver speaks. This time he’s clearly announcing the next stop. I feel a vein in my neck pulsing as the doors close. Did I just blow my last shot at funding?

               My entire body is shaking as I read. “Odd coincidence. Sitting across from our 11 AM.” The train lunges forward. “He has given me a demo of his product…”

               My legs lose the ability to hold my weight. I sink down into my chair.

               “App sellable as is. Has the drive to make it succeed!!!”

               “Will need sales / marketing support. Please begin drafting the documents… Suggest we fund at $100k.”

               My hand is still shaking when I hand her phone back.

               “I thought maybe we’d go for breakfast,” she says pulling me out of my stupor. “There is a great spot at the next stop.”

               “Yeah,” I took a deep breath. “I guess we should go over the details.”

               “Absolutely,” she said. “We should definitely do that.”

               Something in the way she says it makes me blurt out, “If you weren’t the investor, I was going to ask you out.”

               Oh fuck! Why did I say that? Did I just find yet another way to snatch defeat from the jaws of victory?

               “Maybe you still should,” she says teasingly. 

               A hundred ill-formed questions flooded my brain. When one finally bubbles to the surface it’s something like: Wait. Does that mean she can date her investees?

               No sooner do I think it than she flashes that brace-filled smile.

               “That is,” she says, mischievous. “Unless I’d be too much of a distraction from your twelve-hour

workdays.”


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Posted On: September 8, 2026
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