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 most likely heavily inebriated. 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.
Uber Passenger Had No PANTS!! 😱
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!
Creepy Encounter—Pickup at an Abandoned Lot
My experiences driving rideshare range from fun to downright bizarre. One of my strangest moments occurred during a pickup request at an abandoned Toys”R”Us parking lot. I arrived to find a person crouching and hiding behind a pile of luggage, resembling a scene from a horror movie. You never really know what awaits on the road!
Challenges of Multiple-Stop Rides: A Driver’s Perspective
I 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?
When Riders Put Drivers in Tough Spots
As a rideshare driver, every day presents new challenges, often differing from the optimistic expectations many have when starting. While driving can be rewarding, awkward situations can arise, leaving drivers feeling uneasy. From dealing with riders eating in your car to tricky pickup spots, it's essential to navigate these scenarios effectively.
Beneath the Surface—An Unforgettable ER Trip
Every passenger has a story. One man shared his struggles with alcoholism, saying, “I’m a terrible husband and father.” After two years of sobriety, he relapsed, missing his daughter's recital and drinking for 48 hours. Despite his beautiful home and successful career, he faced deep internal battles.
What to Do When a Rideshare Pickup Turns Sour
Upon reaching Home Depot for a rideshare pickup, I found my passenger waiting with several bags of wet mulch and gardening supplies that I couldn’t fit in my Tesla. When I calmly explained the situation, he grew frustrated and started yelling, creating a tense atmosphere.
Insane Psych Ward & Rehab Rideshare Pickups
Riders often test your patience, presenting challenges that can range from trying to offload a drunken friend to transporting a patient back to a mental health facility. Sometimes, you may not grasp the situation until you arrive. So stay vigilant—you never know what surprises
Confessions and Connections—Passenger Shares Dark Secrets
Many people hop into my vehicle, ready to divulge their life stories and secrets—often more freely than they might in a confession. One unforgettable trip was a commercial pilot who, despite his success, opened up about feelings of hopelessness and regret. His honesty emphasized how anonymity fosters connections.
The Time I Drove My Drunk Property Manager
I finally gave a ride to someone I knew while driving for Uber—my property manager! As she got into my car, her messy appearance and the strong smell of alcohol were surprising, revealing a wild night out. But don’t worry, your secret is safe with me—at least until you decide to hike up my rent!