I drove Uber and Lyft from 2016 to 2019, off and on, whenever this freelance life required. Recently I was reading back through some of those posts where they sit on my old website, and I was reminded of how much like a confessional booth my car became during those days. You might find it hard to believe the kind of things someone might be willing to tell their Uber driver.
I thought I’d repost a few of those stories here, edited and updated, from time to time. I hope you enjoy them!
I drive up Queen Street at that time of day when the late night starts to become early morning. In other words, sometime between 2 and 4 a.m. Our little city sleeps hard during those hours, even on weekend nights, and while I pass a few small groups of college students downtown, winding their way back to their dorm rooms, once I get north towards the train station, the streets are empty.
One of my ride share apps signals a customer is waiting, so I weave my way through the dark streets and alleys to a nondescript corner, one that looks like any other, and I see a young woman standing off in the shadows. When I stop, she drops her cigarette to the sidewalk and grinds it out with her toe, then slips into the back seat, bringing in the smells of the night with her.
She is dressed in all black, her hair died black, with black lipstick and dark, dark eyeshadow. She gives me a sad smile in the rearview as she settles into the seat.
I confirm her destination, assume no sane person wants to talk at that hour, and drive away from the curb. The streetlights seem lonely. There is no traffic.
I should take a second and tell you this: I love music. I play music all day, every day, from the moment I walk into the kitchen in the morning until I fall asleep at night. If it was up to me, I’d sleep with music playing, but Maile can’t sleep that way, so I gave it up in the early days of our marriage. All that to say, I love music.
And as I drive this young woman from here to there, a song I love comes onto the playlist: “Tennessee Whiskey,” by Chris Stapleton.
Used to spend my nights out in a barroom
Liquor was the only love I've known
But you rescued me from reachin' for the bottom
And brought me back from being too far gone
By the end of the first verse I am humming along, enjoying that smooth song on a dark night heading towards morning. I am so tired. A good song will keep me awake just about every time.
But then, something surprises me: by the start of the second verse, the Goth girl in the back starts singing along with this country icon, Chris Stapleton. And not quietly. She’s singing like she’s in the shower, as if there’s no one within a hundred miles of her, or if there is, she doesn’t care a bit.
I've looked for love in all the same old places
Found the bottom of a bottle's always dry
But when you poured out your heart I didn't waste it
'Cause there's nothing like your love to get me high
When Stapleton hits that high note at the end of the second verse, when he draws out and sings the word hiiiiiiiigh, it’s an experience, and here this girl is, belting it out, matching him note for note…and she’s amazing. Her voice is incredible. I’m stunned.
She continues singing along with him, and I just listen. Who is this young woman? Surely, singing is her profession. She has to be someone famous. Listen, I’ve tried to hit those notes, and I’ve been with others who have also tried to hit those notes, and let’s just say it doesn’t usually work out for anyone involved. But this was majestic.
The song winds down and I pull up in front of her destination, speechless, still completely shocked at the talent of this singer. She gathers her things in that early morning darkness, makes eye contact with me again in the rearview mirror, except this time her smile is bright, her eyes alive.
“I love that song,” she says simply, and she climbs out of the car. That’s it.
I love that song.
I think about this story now, and it is years in the rear view mirror. Probably five years ago. Yet every time the song comes on, I tell my kids the story about the Goth girl in the back seat of my car who sang Tennessee Whiskey better than Chris Stapleton.
Remember that post I published here about two weeks ago, “Living a Life That Has No Rational Explanation”? Well, today Maile and I are chatting about the same topic over at our podcast, “The Stories Between Us.” You can check it out here: “This Unpredictable Freelance Life.”
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I loved these stories when you first published them and I'm loving them again now. Thank you for resharing. This is just the reminder I needed on a cold, dark, and silent Illinois morning.