Driving Rideshare MDW in Dewey—Absolute Insanity!

Just two weeks into my journey as a rideshare driver, I found myself on the cusp of Memorial Day Weekend—the unofficial kickoff to summer at the Delaware Beaches. An invitation from a friend to stay at Dewey Beach, also nicknamed the “drunken mile,” felt like the perfect opportunity to dive headfirst into the excitement. This same friend had previously driven rideshare during MDW and had raved about the experience—non-stop trip requests, insane surges, and a vibrant crowd of energized vacationers.

He was absolutely right! Saturday night marked my debut in Dewey Beach, and it was everything I had hoped for. Despite my unfamiliarity with driving rideshare in the area, I managed to navigate it successfully, chasing surges and making an impressive nearly $300 in just five hours. The energy from my passengers was intoxicating, but it wasn’t just because many were inebriated; it was the pure, unfiltered joy of a three-day weekend getaway. This wasn’t the usual grind of city commuters lost in their phones, but rather an exciting escape from the daily hustle.

One unforgettable pickup occurred at a house party in Rehoboth Beach. These weren’t ordinary beach gatherings, but extravagant parties hosted in sprawling McMansions, often organized by visiting members of the LGBT communities from DC and NYC. As I arrived at a beautiful 3-story beach house and parked out front near a giant blown-up unicorn, a trio of men waved enthusiastically. Still new to rideshare and a bit naïve, I rolled down my window and asked if any of them were Danny.

“I can be Danny if you want me to be!” one of them yelled, laughter erupting from the group. They were clearly having a great time, and I found myself caught up in their playful banter, even as I waited for my actual passenger.

I explained to them that I was an Uber driver here to pick up my passenger—Danny. 

“Oh, I think I know who Danny is,” one of them said. “He’s busy having fun inside,” another one chimed in and they all began to laugh again. “Why don’t you come inside as we can all have some fun!” they continued to tease. 

I chatted with them for a few more minutes. Amused and flattered that they kept hitting on me. But also starting to get annoyed as the minutes ticked by, waiting on Danny so that I could make some money. Remember, these were the Wild, Wild West days of rideshare—meaning, that I did not get paid a cancellation fee if my passenger didn’t show up.

Eventually, Danny made his appearance—but not without a memorable entrance. To my surprise, he was holding his pants in one hand, revealing a glittery tank top, a sailor hat, and… well, not much else. The laughter from the group intensified as they took in the sight, and I couldn’t help but chuckle as I welcomed him into the car.

My passenger had no pants—revealing only a red thong. However, he appeared to be carrying some sort of spandex-style bottoms that were torn from the crotch area.

“Have fun with that, Charles!” as laughter erupting again from that group of dudes as I pulled away from the house party with passenger in tow.

After Danny and I exchanged pleasantries, he then immediately dialed a friend and began venting about his dating mishaps in vivid detail, seemingly oblivious to my presence. I felt a mixture of embarrassment for him and myself as he animatedly shared his most recent dating and sex stories, completely ignoring that I was there. Even going into horrid detail about what happened that night and how his pants got ripped.

As soon as we reached his destination, he hopped out, still on the phone, and I was left with quite a surprise—sweaty, oily ass prints on my backseat! Thankfully, my leather seats made cleanup a breeze, although I made sure to don some gloves for good measure. This trip introduced me to the insanity Dewey beach had to offer as a rideshare driver during Memorial Day Weekend. And there was no going back!

Sunday proved to be even more of a whirlwind. I dubbed it the last “hurrah” of the weekend, where people truly let loose, fueled by the anticipation of summer and the fact that most had the day off on Monday. The atmosphere was electric, and I reveled in the opportunity to connect with passengers who knew how to enjoy themselves responsibly. Unlike the college crowd, these vacation drunks brought a certain vibe that felt carefree and fun, with hardly any antics or messes to clean up.

By the end of Sunday night, I had already netted $300 before hitting the peak hours leading up to bar closings. When I finally dropped off my last passenger just after 2 am, I had an astonishing total of $464.80 in my app—not including tips!

After an exhilarating Sunday night filled with laughter and lively vacationers, I found myself unable to resist the allure of one more day behind the wheel. I decided to stick around and drive on Monday, even though I knew traffic would be a nightmare and surges would likely be scarce. The thrill of meeting entertaining drunks and the substantial earnings from the weekend had me hooked—addicted to the energy and the excitement.

However, the high of the weekend would soon come to a close. I accepted what would unknowingly be my final passenger of the Memorial Day Weekend. My mother always warned me that all good things must come to an end. And the final passenger seemed pretty chill, but I sensed the vibe of the day was shifting.

As I pulled up to a newly constructed, very expensive hotel right off the boardwalk in downtown Rehoboth, I rolled down the windows of my Honda Accord to greet the passenger. The sun was high, feeling the warmth of it piercing through my cracked sunroof; and the ocean breeze was strong, bringing the smell of fresh, salt water inside my Honda Accord.

“Hey, how’s it going?” I asked the passenger waiting on the curb. He looked the part—a crisp white button-down linen shirt and tight khaki shorts that accentuated his physique, complete with stylish sunglasses, backpack, and duffle bag.

“Can I put these in your trunk?” he asked, dismissing my greeting altogether. “Of course!” I replied, stepping out to help him with his bags. “Looks like you’re heading to Ocean City, Maryland?” I made small talk, trying to mask my disappointment at the direction my ride was taking.

“Yep, and please hurry; I have a bus to catch to DC,” he replied sharply. The tone set the stage for what would be a very different driving experience compared to the previous nights. With traffic crawling and requests dwindling, Monday was shaping up to be all business and no fun.

“Got it,” I said, reassuring him that traffic was mostly headed north. “We shouldn’t hit much resistance on the way to your destination.”

As we started our journey, he loosened up a bit, but not before giving me a few requests. “Can you turn down the radio and adjust the air conditioning?” The thrill of driving lively drunks around was quickly replaced by the feeling of being a taxi driver, catering to a passenger who seemed more focused on his phone than the ride itself.

“Sure thing,” I replied, trying to keep the interaction polite as we drove in silence. A few minutes before we reached his destination, he finally looked up and shared, “I’m not looking forward to that bus ride. Too hung over.”

Curious, I asked if he had been out bar-hopping the night before. “Nope, just had some friends get married at the hotel you picked me up from, and the party went on all night.”

“Sounds like a good time!” I said, trying to keep the conversation flowing. He then lamented about not having time to grab a bite to eat before heading out. My stomach echoed his sentiments—after a long morning, I was ready for something substantial.

“I was actually thinking about getting something to eat myself,” I mentioned. “Any places you recommend?”

“Oh yeah! There’s a brunch spot called Bad Monkey. We’ll pass it on the way to my spot.” Perfect! I thought. I was eager to grab a meal before embarking on my long drive back home.

As we approached his drop-off point, I wished him a quick and safe trip on the bus back to DC. In a surprising twist, as I unloaded his bags from the trunk, he handed me a $20 cash tip. “Here’s for your troubles. Hopefully, you enjoy your brunch.”

Honestly, given how the ride began, I didn’t see that tip coming at all! After he exited, I decided to drive a few blocks north to Bad Monkey. The well-deserved meal was just what I needed.

As I sat there, savoring my food, I couldn’t help but reflect on the whirlwind of the past few days. The wild passengers, the unexpected moments, and the thrill of rideshare driving had me contemplating how I could turn this gig into a full-time adventure. Memorial Day Weekend was over, but the memories and excitement lingered, leaving me eager for what the summer would bring.