The Best Uber Ride, Ever

Best ever is a pretty bold claim to make. It stakes the claimer’s reputation on the idea that among all others this one reigns supreme.

I promise you. I have the best ever Uber ride story for you today.

Buckle up.

First, I had to share with you the summary of our time in Pittsburgh, otherwise if I told this story you would have been all like, Jess, when did you go to Pittsburgh?! and then it would have ruined the narrative of the Uber story.

So, important backstory: We went to Pittsburgh.

The night of our food tour, we made reservations for dinner at Senti, our favorite stop on the food tour. We wanted to spend a little time after dinner at Rivers Casino, so we decided the best plan was to park our vehicle at the Casino, and get an Uber back and forth from the restaurant.*

*You never know what the parking is going to be like at night in a city.


Final destination: Senti

I’ve taken Uber rides in some pretty major cities including LA, NYC, Miami, and Honolulu. Sometimes you get a driver who says hello and then there is no further conversation from the point of hello until the point you exit their car. Sometimes you get a driver who wants to talk: Where are you from? What are you doing here? What sights have you seen? Blah, blah, blah. I’m fine with the small talk and usually I return the favor with the same responsive small talk questions I’m sure they have answered dozens of times: How long have you been an Uber driver? Do you do this full time? Are you originally from this city?

I’ve experienced drivers who rag on the economy and politics, drivers who demand we give this or that restaurant a try, and even a driver who wanted to tell us about a new app he is creating which is going to earn him millions.

But nothing prepared me for the drive from the casino to Senti that night.

We got into the car and, since we were leaving the casino, the obvious first question for our Uber driver to ask was, “So, how’d you do? You get lucky in there?”

We explained we were coming back to the casino after dinner and, now showing his hand as a talker, he went into the other formalities.

“Where are you from?”


“Oh alright, I know Jersey,” he said, and proceeded to mention Cherry Hill and Philly.

We returned the gesture of chit chat and asked, “How long have you been doing this?”

We found out our driver used to work at the William Penn Hotel downtown. Having stopped in front of the William Penn Hotel during our bike tour earlier that morning and learned a thing or two about its history, we perked up with interest.

He proceeded to tell us he worked as a bellhop and due to the prestige of the hotel was able to meet several celebrities over his tenure there. Personally, I would have been impressed with one or two names. But, friends, the man began to ramble off a clearly rehearsed list of names ranging from political to athletic to entertainment celebrities across the nation.

We were impressed into gasps of silence, because how do you respond to a man going breathless over sharing a list of celebrities whose luggage he carried?

Was a gut instinct? A strange case of  déjà vu? I don’t know. But something told me the wild ride which was this Uber had only begun.

More small talk continued after his reciting of the great celebrity proclamation, yet in it, I found our driver slightly distracted. As we were talking, I watched as he put a CD into his CD player.

This was clearly a move made with purpose.

At the first sound of silence, he asked, “Do you guys like jazz music?”

As a matter of fact, I love jazz music.

As a second matter of fact, Hubby hates it.

Two of us ho hum a response of approval towards the genre as the CD begins a clearly home recorded back track of a jazz tune. A couple bars in and our driver produces a clarinet which has been resting on his parking brake, awaiting its time to shine.


For the remainder of our ride,* his hands never left the clarinet, save for moments when a left or right turn were required.

*Which was no more than fifteen minutes, but no less than five.**

**I mean, the man was playing a clarinet while driving. How on earth was I supposed to keep track of time?*** There were a lot of other things I needed to focus on, like were we going to get hit by another car?!

***However, I know he played more than one tune.

He was so into his music, he drove right by the restaurant. He made an offer to swing around*, to which I quickly responded, “No. We’re good, thanks.”

*Which Hubby is convinced really meant put the car in reverse until we were back in front of the restaurant.

At dinner, we were so blown away by the ride we told our waitress about it. And she told us she and her boyfriend had him drive them. Twice.

And that, friends, is the tale of The Best* Uber Ride…


*Best refers to the story we went home with, not necessarily the driving experienced in this Uber ride.**

**In other words, friends, don’t try this at home. Please.



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