It was after dinnertime in May 2017. The streetlights were just turning on. And I was driving with my windows down on the way to University of Delaware campus area in Newark, Delaware. It is that time of year where you can just sense summer is right around the corner. A cool, brisk mid-May evening, but just enough humidity in the air to want to stand outside and drink.

And tonight was going to be my first night Ubering. In a college town with nice weather breaking after a long, cold, damp Spring. I was told that a busy, populated area with lots of shops and bars would be ideal for picking up Uber rides. And Main Street Newark, Delaware this time of year is that such place.

I thought about driving to busier, populated areas, such as Wilmington, Delaware or West Chester, Pennsylvania. But I wanted a smaller town setting that was busy enough to make some quick bucks, but not too difficult to navigate. Because if something went wrong, I wanted to be in a comfortable setting. Since I was new and just trying this Uber app thing out.

I can still remember how nervous I was when I opened the app and went online for the first time. Picking up strangers from the internet. At night. In a college town. And they’re probably drunk. The first night was genuinely nerve-racking! And it’s crazy thinking this now, with thousands of trips under my belt.

Ironically, I searched YouTube for Uber tips, and only a few videos surfaced about the importance of a clean car and supplying water and mints for riders. Nothing at all about what it was like to be an Uber driver and how to interact with riders. That has definitely changed! Since there’s now endless amounts of Uber content on YouTube from a rideshare driver’s perspective.

How do I act? What do I say? Do I act casual, or more like a servant or butler? I usually over think everything. But I felt totally unprepared for this moment. I know it seems ridiculous now that I replay these thoughts that were going through my head back then. But rideshare was novel and like no other experience to compare.

I’ll never forget the first time that Uber ping came across my iPhone. I was waiting for over an hour when I finally thought, “this is it! I hope these people are chill.” Because I had sweaty palms, and you could probably smell the fear from far away. So, I’m sure whoever I was picking up would definitely notice how nervous I was.

My first trip ended up being a group of college girls that I picked up from their dorms. And I’ll never forget this experience! They were young, attractive, and loud. And here I was, a 32 year-old man picking up picking up four college-age women from their dorms and driving them to a popular college bar. It just felt weird.

And I was right, they picked up on how nervous I was as soon as they got in my car. Since I’ve never taken an Uber before at this point, and I had no idea how I should interact with riders. I had zero idea if I should act casual or professional. And I couldn’t shake off the weird feeling that I just let random strangers from the internet in my car. And I’m getting paid for it!

But these college girls were awesome. They were relaxed and confident. And quickly realized that this was most likely my first night driving Uber. And as I was struggling to figure out how to start the ride on the Uber app, one of them shouted, “wait! Is this your first night as an Uber driver!?”

“No,” I answered. “This is my first ride, ever.”

“Uber Virgin!” They all shouted at once. 

And as the saying goes, the rest is history. That ride paid a measly $3.86. And I did several other small rides around that college town before heading home for the night. For a whopping grand total of $22.77 in rideshare earnings. 

But I was HOOKED!!