Chuck Stories
This is a collection of my craziest rideshare stories from over the years! Driving rideshare is a blast because you truly never know who you are picking up next. Each ride is like a mini-adventure, filled with unexpected encounters and surprises. And each ride has the potential to become a memorable tale.
First EVER Uber Ride - “Uber Virgin!”
I was extremely nervous when I went online for the first time. Picking up strangers from the internet. At night. In a college town. And they’re probably drunk. This first night was genuinely nerve-racking!
How I Became Addicted to Driving for Uber
The night began with the familiar chime of a trip request as soon as I turned on the Uber app. It was the start of a wild ride! The notifications kept coming—one ping after the next—as I chased surges from one college town to the next.
Driving Rideshare MDW in Dewey—Absolute Insanity!
Just two weeks into my journey as a rideshare driver, I found myself on the verge of Memorial Day Weekend, the unofficial start of summer at the Delaware Beaches. The energy from my passengers was intoxicating, embodying the pure joy of vacation and a welcome escape from the daily grind.
Passenger Question—Do You Do Coke or Hardcore Drugs?
I’ve had my share of unusual passengers, but this ride was particularly bizarre. It involved a seemingly drunk passenger, whose intense gaze and odd questions about drugs made for a short but unforgettable experience.
Passenger Request—Can You Buy Me Liquor?
As a rideshare driver, you encounter a variety of passengers, each with unique quirks and unexpected requests. One of the most bizarre experiences was when a passenger asked me to buy her liquor with my own money, highlighting the strange dynamics of rideshare interactions.
Rideshare Drivers: The Unofficial Therapists
As rideshare drivers, our interactions often transcend typical transactions. Drivers have the power to make a significant impact simply by being present and attentive, embracing the role of an unofficial therapist behind the wheel.
From Stormy Starts to NYC Skyscrapers
I received a request for a 45-minute trip that promised adventure. Picking up two scantily dressed women, they offered a $100 cash tip to take them to NYC. What began as an ordinary day quickly turned into a wild ride filled with unexpected conversations and lessons on the unpredictable nature of driving rideshare.
A Rideshare Journey that Almost Happened
Often, the most captivating stories emerge from the journeys we choose not to embark on! However, the narratives we create in our minds about the thrill and adventure of unexpected Trip Requests can be just as enjoyable as the ride to the destination itself!
Driving Rideshare MDW in Dewey—Absolute Insanity!
Just two weeks into my journey as a rideshare driver, I found myself on the verge of Memorial Day Weekend, the unofficial start of summer at the Delaware Beaches. The energy from my passengers was intoxicating, embodying the pure joy of vacation and a welcome escape from the daily grind.
Challenges of Multiple-Stop Rides: A Driver’s Perspective
AI often find it frustrating when passengers add a stop after I’ve already picked them up, as it complicates my route and compensation. Recently, a passenger named Brycen wanted to stop for freshly-made food during a busy time and expected me to wait while he ordered.
Most Bizarre One-Minute Rideshare Experience
This was one of the strangest starts to a rideshare trip that I’ve ever had—lasting less than one minute! My passenger was VERY intoxicated and confused about his destination. I couldn’t think of any past trips that started like this and ended so abruptly.
Passenger Refuses to Leave My Vehicle!
A chaotic situation unfolded when a passenger refused to leave my vehicle. I picked up two passengers at one stop, headed to two different destinations, but only one stop was logged into the app. What could possibly go wrong?