AI generated ink and watercolor image of a smiling young woman in the back seat of a car during a rideshare trip.
AI's rendering of "Winnie," my warm-hearted, well-read passenger.

Notes from the Road: “Winnie”

The app told me her name was Winnie. I’d never met a Winnie, so I was pretty keen to see what one looked like. I picked her up at some house party off campus, and even though she made me wait long enough that I was eligible to cancel and get a fer-yer-trubba fee instead of a demerit, I was feeling generous. A bunch of guys and gals were making playful asses of themselves out on the snowy lawn. It must’ve been quite the party, too. I saw a whole lot of stagger for a school night, and a young stud with no shirt pissing into the hedges just off the porch.

Then Winnie was in my car with a breathy, Holly Golightly apology for making me wait, and we were off.

The car I’m renting, a Ford EcoSport (just…don’t) with it’s rear passenger windows tinted to the legal limit, has a dark backseat to begin with, and, it being after midnight, the passenger compartment was even darker. Before the dome light shut off as the door closed, though, I could see that she had straight, sandy-brown hair that hung to her shoulders.

I’ve never been a huge fan of straight sandy-brown hair that hangs to a girl’s shoulders, but her hair was thick, and it curved forward a little bit at the ends, suggesting a hidden vitality that the first 10 inches didn’t reveal. I don’t try to look at my customers. Not as a rule. A lot of them seem pretty bashful about the whole rideshare affair.  Others are perfectly comfortable — they just try to avoid being memorable whenever possible, if you know what I mean. And that’s fine with me.

And it would be fine with me if this Winnie didn’t want to be looked at or remembered. But we got to talking. What the first subject was, I can’t recall — it seemed like we ended up talking about just about everything during a pretty short drive. You just make eye contact, like that, in conversation. It took me years to practice making myself look folks in the eye; it’d be weird to try not to now.

Winnie had just a hint of wine on her breath She was probably one sheet to the wind, but no more than that. Just feeling loose and amiable. She’d told me that she was a bartender, so she probably gets to see any variety of sloppy drunks she might care to and doesn’t need to model that behavior herself. She told me that most of the bartenders at the tavern where she slung brews and cocktails were guys — rough and ready types. She laughed and said, maybe a little embarrassed, that she was the squishy, emotional bartender, and let out a chuckle that deflated into a sigh.

She laughed a lot during the conversation. Not the tight chested, measured type of laugh either, but little impromptu explosions of humor that put a guy at ease. I’m not sure how we started talking about children’s books, but it was pretty clear that her squishiness extended beyond lending a sympathetic ear to misty-minded patrons. And she knew her children’s books, too — not sure why, and we didn’t get into it. She was going to school part time, so who knows? Maybe she’s a Lit major. But we talked about our favorite children’s books, and I said, “You know the book that you should have on hand at all times? Just in case you’re in for a bad day? Buttercup’s Lovely Day. A few pages into that will cure most anything that ails you emotionally,” I told her. She told me about some book with beautiful illustrations with “mouse” and ”wolf” and something else in the title. I haven’t googled it yet. I keep meaning to, but then I don’t.

Like I said, I don’t try to get a look at my customers as a rule. Not unless I think I’m gonna have to describe them to a police sketch artist, anyway. But as we drove up 116, I couldn’t help it at least a little, as we glided under street lights, just a glance in the mirror now and again. Just to get a glimpse here and there of whatever the racing splashes of yellowish glow might reveal. I tried to piece together the puzzle of her face. A chin. An eyebrow. Lips fluttering mid sentence. She was pretty. Not that dainty, delicate kind of pretty. She radiated that girl-next-door, with about 25% tomboy, kind of allure. Sculpted cheekbones and jawline perfectly framed by that shoulder-length straight hair that curves forward at the ends. How does it do that?

I’m a sucker for nice cheekbones. If I had to choose? I’d take great cheekbones over a great ass any day. You get more chances to look at a girl’s cheekbones. I never got to check out Winnie’s ass, and that was just fine. I was elated enough, just having some evening conversation that carried a little warmth for a change — not the cold, clipped, transactional exchanges I’ve grown used to. And I have to say, a couple of times when I looked in the rearview, I saw that she was looking back into my eyes, too. Not in some kind of assessing, scrutinizing way, either, but like we were right across the table from each other at a coffee shop, and not in the divided universes of driver’s and passenger’s compartments. Rather than turn away, she really leaned her gaze into it, and smiled broader and nodded her head as if to acknowledge whatever I was saying, or to emphasize the point of whatever she was saying.

The voice of the app interrupted to let me know that I had to turn on the next street, her street, which was coming up, which I did. I felt a little deflated, I won’t deny it. I pulled into her drive, and said that if she ever happened to get me as a driver again, we could continue our talk about children’s books.

She told me I didn’t have to leave it up to chance. Why not show up at the tavern and have a beer and we could carry on that conversation in-between her serving customers, she wanted to know. Pretty sure I’d had breath in my lungs when I stopped the car. Damned if I could find it now.

Finally, I said, “well that just sounds crazy. I might have to take you up on that.”

Then she followed with, “but I’m going out of state for a week or so, so if you do come by, make sure it’s after the 1st.” And the blood rushed from my head like someone pulled the bathtub plug.

Now, almost day after she occupied a space 24 inches away from me in my gig-mobile, I’m thinking that my view of her in the mirror must have been wayyyy more accurate than her view of me. Or maybe she’d had more to drink than I thought. Or maybe she’s just one of those rare, magical people who escaped the curing, hardening process that condemns the rest of us to seeing the world through an increasingly guarded, polarized filter.

And then, just like that, she gathered her things and threw open her door. She drifted out of that back seat like a flock of champagne bubbles, escapees from some delicate flute, floating off into the night. I backed out of her driveway, switched the app off for a while, and drove to a fast food joint to fuel up for the next few hours. And to scratch my head and try to figure out how much effort you’d have to spend on staying in a good mood to predict a fair return on the investment.

I looked at my phone to see exactly what day the 1st was and then closed the calendar app. I shut off my phone too as a precaution and slid it into my shirt pocket. I’m not going to drop in and carry on our discussion after a week or so. In fact, I know I’ll never set foot in that pub after the first of the month. But I may go buy a copy of Buttercup’s Lovely Day and just leave it there on the bar with a sticky note that says, “For Winnie — stay squishy.”

Jason Velázquez

Jason Velázquez has worked in print and digital journalism and publishing for two decades.
Phone: (413) 776-5125

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