1. Chasing

Where are you?

Uber passengers text me this every single day. The obvious answer? I’m waiting at the green pin on the map, right where you told Uber to send me. That answer should be enough, but somehow, it never is. Late nights, alcohol, and life itself make simple things, like finding your Uber, far more complicated than they should be. Maybe the better question isn’t where I am. 

Or maybe the real question is: where am I going?

It’s 2 a.m. on a freezing Saturday night that makes me question my life choices, specifically, the one where I quit my job to drive an Uber. I find myself parked in Armory Square, Syracuse’s Brooklyn-wannabe downtown. Every small city in America has its version of an urban revitalization zone, complete with craft breweries, Starbucks, inexplicably surviving boutique shops, and restaurants serving things like chicken and waffles with hot sauce.

The temperature has plummeted to negative ten or something close to it. Snow and ice battle for control of my windshield while hordes of underdressed 20-somethings stumble out of bars, shouting into the night. Their eyes flick between their phones and the swirling snow, trying to locate their Uber. We drivers are lined up, blocking traffic, scanning the chaos for our passengers. The police honk their sirens, trying to move us along. No one listens.

My passenger, Jennifer, hasn’t responded to my texts. To be fair, drunk or not, most passengers never do. I waited five minutes, just a few more before the ride was canceled. But I need to get this ride started. I’m exhausted. I’ve been driving 12 hours and 300 miles. I signed up for an Uber bonus called a Quest: 50 trips equals a $100 bonus. 49 trips pay $0. This ride gets me to 49, meaning Uber will immediately send me my 50th.

A girl, maybe it’s Jennifer, I don’t know, but this woman stumbles across the street and bangs on my window, shouting.

Are you my Uber!?

Let’s pause for a second.

How should an Uber driver respond? I want to say, Hey, dummy, how do I know? Because all I know—all any Uber driver knows—is that I’m picking up someone named Jennifer, who may or may not be the drunk girl currently shouting at my car. For all I know, Jennifer ordered a car for Bob and his friends. I hesitate, because the only thing standing between me and a total stranger climbing into my car is a single name.

The passenger, the one who ordered the Uber? They know everything: my car, my license plate, my position on the map, my arrival time. They even have a picture of me.

I have a name. That’s it.

Thankfully though, she says that she’s Jennifer. And by the looks of it, Jennifer is in bad shape. Her friends, equally drunk and unreliable, ask if she’s going to be okay. The answer is always no, they’re never okay if you have to ask if they’re okay. She’s right here, though, and now my problem. Someone’s daughter. Too drunk to notice she’s freezing. I can’t just leave her.

We pull away, and I hear the window roll down. I shout at her to keep it up, but she doesn’t respond. It’s always the silent ones that puke. I glance back—her head sags against the window, eyes shut. Before I can react, she leans out and empties the night’s fun onto the pavement.

I jump out, open her door, and step back, shivering. She sobs as she pukes. They always cry. She insists she never throws up, apologizing between retches.

Then she looks up at me, pitiful, vomit-matted hair sticking to her face. She asks me to hold her hair back. I step into the splash zone, doing as asked while she dry-heaves.

A few minutes later, I handed her a towel. When we start driving again, she rolls the window down again. This time, I’m too late to pull over. She throws up down the side of my car.

I’m sorry.

The damage is done. I don’t stop. We’re a block from her dorm, and my Prius now has an icy vomit mural frozen to its side.

There are no open car washes at 2 a.m. at -15 degrees. Even my home hose won’t work. The puke is a problem for me in the future. My night? It’s over. There is no bonus.

I’m a nutrition student. Sorry.

Always tears. Always apologies. She even tries to use my rag to wipe her vomit off the car.

I’ll tip you in the app.

I don’t drive away immediately. I’ve heard stories—drunks slipping on ice and freezing to death. I wait until she’s safely inside. She’s someone else’s problem now.

She kept her promise though. A $5 tip. Along with Uber’s $150 cleaning fee, I head home, car reeking, fingers frozen, wondering: where am I?

Where am I? I’m right where I’m supposed to be. Somehow, it never seems to be enough.


Now the fun part. This book can be read two ways.

You can take the traditional route, turn the page and read straight through, front to back. That’s the well-paved road, the direct shot from start to finish. If that’s your style, turn to Essay 2: Confessions.

Or, you can choose your own Uber adventure. At the end of each essay, you’ll decide where to go next, just like I do every time I turned on the Uber app. If that’s your style, here are your first options:

  1. If you want to hear what passengers reveal when they think no one is listening, you’ll still turn to Essay 2: Confessions. (I know, sorry, but this is probably the last time the essays are in sequence.)

  2. If you want to see the moment I first questioned everything, the ride that made me consider leaving my career, turn to Essay 3: Epiphany.

The choice is yours.