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!

New Chuck Story Posting Soon!

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?