There can be a few surprises when you drive people around for a living. But the story I'm about to tell you has got to be the craziest one when it comes to Uber stories.
First, a bit about me: I'm 61-years-old, and I've been divorced for about 2 years, which happened after a long marriage. We had no kids, and I thought we were happily married, so it really set me back when she told me she wanted out. Turns out she had been having an affair with my longtime business partner. I forced a buyout of my share of the business in Los Angeles, and between that money and selling the house, it gave me an opportunity to just take some time to think about next steps for me. With no kids and no close family, I could make whatever choice I wanted.
After getting everything settled, I first traveled for a while, and then ultimately ended up in Denver as a place I thought I might like to be. It was near the mountains so I could go skiing in the winter, which I had loved to do early on in my life and hadn't done in years. Another reason for Denver was that recreational marijuana had been legalized in Colorado, and now that I didn't have a bunch of responsibilities, getting high on occasion had some appeal. I had come of age in the 70s after all, so smoking weed was something I wouldn't mind picking back up again after so many years without partaking very often.
Once I got settled in Denver, I started doing a bit of driving for Uber, simply as a way to explore the city and to make a bit of extra cash while I was figuring out what to do with the rest of my life.
So that's the setup for the day I met Cheryl. I was driving down Colfax just south of the Denver Zoo one morning about 10 am. I like to drive early mornings and am normally done by this time, but it was kind of a lazy Friday and I had nothing better to do that day so just kept the Uber app on. A ping popped up that said a rider named Cheryl needed a ride and was at Voodoo Doughnuts, just up the street from me.
My first thought was "mmmm...doughnuts," and I then thought I hoped she wasn't going far, because I thought I could swing back around after dropping her off, pick up a couple for myself, and then go home and devour them after a couple of bong hits.
As I pulled up to the curb, I noticed there was a dispensary on the corner as well. Weed and doughnuts! Honestly, what a crazy world we live in these days. Now I was definitely coming back.
I see a young woman, perhaps late 20s, standing at the curb with her phone in her hands and I pull up next to her and roll down the window and ask, "Cheryl?" At that moment, I realize we knew each other. We not only live in the same neighborhood, but we had run into each other at the park a few times, walking our dogs, and a couple of times at a local coffee shop. But we'd exchanged just the smallest amount of small talk in those moments, so it wasn't as if we really knew each other. She did remember my name, though, which surprised me.
"Hi Jeff!," she says with a smile. "What a funny coincidence." She opens the front door and begins to get in. As she does, I reach over and get the front seat moved back for her. Most riders sit in the back, so I normally keep the front seat way up. Cheryl sits down just as the seat is going back, which creates a bit of a surprise on her face.
"Oops, sorry about that," I say. "I was just trying to give you some room!"
"No worries. It just caught me by surprise. Here, can you hold these while I get buckled up?" she asks, as she hands me two bags without waiting for an answer.
One of the bags is clearly doughnuts, because it's a Voodoo-branded bag. And the other? I can smell weed a mile away, and this bag definitely had some in it.
"Well, well, well," I laughed. "Clearly you've been reading my mind," I said as I handed her back the bags.
"What do you mean?"
"Pot and doughnuts...breakfast of champions," I said with a smile.
Cheryl's face flushed a bit, and I worried that I had been a bit too forward with my comment. We were nothing more than casual acquaintances who happened to live near each other. Had I crossed a line? However, she immediately relaxed though, and turned to me with a smile.
"It's been a long couple of weeks. I turned 35 last week, and work has been a bit overwhelming. I've got three days off and I decided to treat myself by kicking it off with a nice lazy Friday of doing nothing. A bit of weed, some baked goods while baked, and a few episodes of Family Guy."
"Thirty-five?" I said with more surprise than I intended. "I had always taken you for several years younger. I guess at my age it's beginning to be a little difficult to know. Anyway, I was just teasing you. It was funny to me because when I saw your location, I was thinking about doing exactly the same thing after dropping you off, although I would have picked the Simpsons or an old movie instead. Great minds think alike!"
We both laughed, and I was relieved that it had ended up as a friendly exchange. I liked being friendly with my riders, but you could never tell how people would take things so in general I was always a bit careful. In this case, because we had met up before I had let my guard down a little, as had she, for that matter.
I should note here that Cheryl is not really close to being what one would call a "beauty." Don't get me wrong: she's cute in a next-door girl kind of way. But she carries a few extra pounds on her and was often without makeup, so always seemed just a little on the plain side. She had long brown hair that she had pulled back into a pony tail this morning, and was wearing sweat pants and a baggy long sleeve top. You know, clothes you might wear if you were just running out for weed and doughnuts! That being said, she did have large breasts, and I had seen her in a tight top once that really made them come alive.
Our houses are within a few blocks of each other, about 3 miles away, and as we headed that direction she asked a few more personal questions than she had asked in past meetings. I gave her the quick summary about how I ended up in Denver, without the details about my wife.
"Married?" she asked, a question I always dreaded a bit. She had never seen me with a woman when we'd run into each other, so I guess she was just being curious.
"Divorced. My wife had an affair, and ...," my voice trailed off.
"Oh, so sorry to hear," she said, clearly a bit mortified that she might have asked something she shouldn't have.
"Hey, don't worry about it," I said. "You just have to move on with life and I've done that."
We drove the last half-mile in an awkward silence. I got to her house and pulled up to the curb.
"There you go, Cheryl. I hope you have a great rest of your day." I paused for a beat, then said with a laugh, "I'm sure you will."
Cheryl paused as well before getting out of the car, as if she was trying to think of a comeback. And what she said next was a complete surprise.
