From Stormy Starts to NYC Skyscrapers

My Longest and Wildest Rideshare Adventure, Ever!

It was the beginning of summer on a humid June morning when my alarm jolted me awake at 5:30 AM. After a few minutes of wrestling with the urge to stay in bed, I finally got up and hit the road as an Uber driver about an hour later. Even though it was only Thursday, the week felt long, as I was on my fourth consecutive day of juggling rideshare driving alongside my regular 9-to-5 job.

The morning weather was a mix of fog and light rain that quickly escalated into a thunderstorm, drenching Newark, Delaware, during my first few trips. The downpour muffled any attempts at small talk with my passengers, who were all quiet business professionals absorbed in their phones. It was shaping up to be an uneventful day.

This would change with a new trip request—a 45-minute ride that had me feeling a rush of excitement and uncertainty. Back in those days, each trip felt like a roll of the dice. It was truly the Wild Wild West of rideshare back then. I knew I wasn’t headed east, as that would take me into the ocean, but the rest was a mystery. The only thing I knew is that I was about to embark on an adventure!

I dubbed these long trips “home runs” because they paid better than shorter or medium length trips. And strategy back then focused on longer trips rather than short ones. Little did I know, this particular ride would be one of my longest and most memorable.

As I drove down a familiar road, I unexpectedly turned onto a private lane I’d never noticed before. After a short distance, I was halted by a gate. Just as I contemplated messaging the passenger, the gate started to open. Good! They knew I was here. Anxious because passengers could cancel a trip back then without penalty. And drivers received zero compensation. 

This private road was lined with McMansions, each nestled nicely into wooded areas on this secluded private road. And my destination was the biggest mansion of them all! Flowing fountain with an Italian-inspired statue greeted me as I pulled into a roundabout driveway that circled the fountain and statue. The backyard of this McMansion was decorated with an in-ground pool and a custom built outside basketball court with stadium lighting.

As I put my Honda Accord in park, immediately stepping outside were two African-American females in their mid-to-later twenties wearing provocative cocktail dresses with furry scarfs or shawls. One woman’s cocktail dress was glitter silver with some sorts of clear beadings, and the other was a pinkish-lace style dress with black stitching. A little outlandish but also not too overbearing.

I was thinking this was some sort of weird Uber ride of shame. The rider’s name in the app was a male’s name but only two scantily dressed women appeared to be going. I had no idea the true juicy story behind this Uber pickup that they would soon reveal. 

I sent them a welcoming wave as they approached my vehicle with smiles. And when I rolled down my window to introduce myself, one of them cut to the chase: “We’re headed to New York, and we’ll give you a $100 cash tip if you take us.” My heart raced—New York City! The potential for that cash tip overshadowed my worries about being late for work.

“New York City?” I exclaimed, a whirlwind of excitement and shock swirling in my mind. I realized I was going to be late for work, but the opportunity was too good to pass up! I needed to message my boss shortly. I still hadn’t had my morning coffee, and I could feel the urge to pee creeping in. It’s been years since my last visit to NYC!

“Yes!” she replied eagerly, “and please don’t cancel on us; we already had two other drivers cancel and been stuck here for hours! We’ll make sure to give you a tip,” she said, sounding desperate. A hundred dollar cash tip on top of the fare was all I needed to hear. She had both guilt-tripped me and dangled a carrot in front of me at the same time. 

“Sure, sounds great!” I happily agreed. “And appreciate that $100 tip,” I added, making sure that she understood that generous cash tip is why I am doing the trip. Though in hindsight, I should have been more direct. And I should have asked for the cash upfront. I was still a relatively new driver, learning the ropes of rideshare life. And oh boy, this was going to be one of those days where I learned the hard way.

“I’ll need to make a quick stop for the restroom,” I mentioned, knowing it was a long trip. I know it’s unprofessional to make stops with passengers in your vehicle. But I thought this was a no-brainer. They seemed less than enthusiastic but agreed.

As they headed back inside to retrieve their luggage, I opened my trunk to assist, saying, “Let me help you with that.” “No, we’ve got it,” one of them replied, as they began throwing their bags into my trunk, carelessly piling them on top of my personal items that I hadn’t yet cleared out. Thankfully, nothing was fragile, as they clearly had little concern for my vehicle or belongings. They continued to haphazardly toss their bags in, demonstrating a complete disregard for my things.

While I was rearranging my trunk, the women climbed into my vehicle and said something like, “Alright, we’re ready, Mr. Driver.” This should have been a warning sign—a massive red flag. However, as someone new to rideshare, I hadn’t yet encountered anything like this or what was about to unfold. I dismissed it as just people being themselves and overlooked their passive-aggressive nudge to hurry me up.

“Okay,” I responded as I settled back into the driver’s seat and started swiping right on the Uber app to begin the trip. “So, it looks like we’re headed to 650 West 34th Street in New York City?” I confirmed. “Yes, that’s a bus stop, and we need to arrive by 9:45 am since the bus departs at 10,” one of them replied.

“Umm, just to clarify, it takes about three hours to reach New York City from here, right?” I asked, glancing at them in the rearview mirror with a puzzled expression. They both looked back at me, appearing confused and slightly disgusted, but didn’t respond. “It’s 8 AM, so we won’t arrive until around 11,” I added, breaking the silence while still parked in the driveway.

“Apple Maps says it’ll only take 2 hours and 15 minutes. Plus, we’re giving you $100, so just speed there,” one of the women said with a snarky tone. That was another red flag I should have noticed. It became clear why two other drivers had canceled on these entitled women earlier that morning.

I tried to explain to them that even if their Apple Maps estimate was accurate, I still wouldn’t arrive in time for them to catch their bus. The GPS wasn’t taking future rush hour traffic into account. Having driven to NYC numerous times in my life, I knew the GPS had never been reliable; it’s consistently a three-hour drive from northern Delaware. Always.

“It’s okay, we know you will make it for us. Just start driving,” one of them said. So, I hit the road. It was obvious they weren’t from the Delaware/Philly area, as they had no idea how long the trip to NYC would take. They believed speeding would help, but it wouldn’t make a difference; we were bound to hit standstill traffic as we got closer to the city.

We had barely been on the road for a few minutes when they began discussing sex openly, as if I wasn’t even there. “I’d take Black dick over White dick any day,” he woman sitting directly behind me remarked. “Yea, that dick last night was nice, big, and thick. And I’ve never gotten that from a White man before,” the other woman in the rear passenger seat added. The woman sitting behind me chimed back in agreement, “Ain’t nothing like some rich, enormous, Black man!” They both giggled.

I was shocked and just wanted melt into my seat, but this horrid conversation continued. They openly discussed their sexual encounters last night with this apparently very wealthy Black man with an enormous phallus. I was curious how they knew this man and how this rendezvous happened. And that soon became clear.

They were escorts for hire who had traveled from Connecticut to Delaware for this arrangement. My curiosity quickly shifted to confusion as I struggled to grasp why a wealthy man would choose these women from such a distance. Surely, there had to be better and closer options available. However, perhaps discretion played a huge part (pun intended) in his decision-making.

Then they began discussing their earnings from the previous night—five thousand dollars each! WTF, I couldn't believe it; someone actually paid these women $5k each to sleep with him. From what they were saying, he was young, attractive, and very wealthy. So, was he blind and drunk last night? Or just foolish, rich, and horny? Because these women were far from impressive—they were absolutely wretched and couldn’t possibly be the best escorts money could buy.

They kept discussing the "date" they had with this gentleman the night before—detailing the food they enjoyed, the lingerie they wore, and the toys they used. I couldn’t help but wonder if those toys were tucked away in one of their bags in my trunk. One of them vividly recounted how she used a toy on herself and their date! After what felt like an eternity of back-and-forth banter about their escapades, they finally shifted their focus to me.

“Have you ever had a strap-on used on you,” one of the asked, speaking up and clearly directing the question at the driver. Not wanting to engage in this conversation and hoping to buy some time, I replied, “Ummm, are you talking to me?” They both laughed, but I still didn’t respond. I just wanted this conversation to be over.

“He’s probably vanilla,” one of them joked. “Yeah, I am,” I replied, hoping that would put an end to their questions about my sexual history. Unfortunately, it didn’t. “What’s the craziest thing you’ve ever done?” one of them pressed on. I really didn’t want to answer, so I stalled again, chuckling and saying, “Umm, I’m not sure. I gotta think about that it.”

“Have you ever had a threesome before?” the other one asked, both of them laughing. “Nahhhhhh,” I replied, drawing out the word slowly. I was beginning to feel very uncomfortable with where this conversation was going. Was I the target of their joke, and were they planning to humiliate me?

They must have sensed my discomfort, as the conversation thankfully shifted away from me. They continued discussing what had happened the night before. These women were unpleasant, vulgar, and crude, making me feel almost nauseous just thinking about it. So even though they mentioned a threesome, it was clear this wouldn’t be my lucky day with these women, as they were not my type at all.

About 20 minutes into the trip, their attitudes began to shift. They went from being grateful to outright selfish brats. I should have recognized the red flags at the start as a warning of what was to come, especially given the long journey and being stuck in a vehicle with them for about three hours. Looking back now, with years of rideshare experience, I would have declined this trip—just like the previous two drivers did. But I knew this long trip would be profitable, and I needed the money.

“But everyone else is going faster than you,” one of them complained. “And I’m giving you $100 to get us there on time for the bus,” she added. I paused for a moment to consider her statement. It seemed to me that she was implying I would only receive the $100 tip if I got them there on time, which was impossible, as I had mentioned earlier. That wasn’t the agreement—the arrangement was that they would give a $100 cash tip for the ride itself, regardless of the arrival time, which was not entirely within my control.

“I’m not getting a ticket,” I began to say, but one of them interrupted me. “You won’t get a ticket. Just get us there so you can earn your tip.” Now they seemed to be trying to renege on the tip, or they were just being plain rude, which I didn’t appreciate. However, I was still relatively new to rideshare and wanted to avoid confrontation at all costs. “I’ll do my best to get you there on time, but I would still appreciate that tip,” I replied, making an effort to be direct while cowardly sidestepping the conflict.

About 30 minutes later, I spotted a rest stop ahead and informed the women that I was going to stop to use the restroom, which was less than a minute away. They looked upset and asked if I could possibly hold it. Seriously? I told them no and reminded them of our agreement that I would need to stop once for a restroom break. One of them replied, “Well, our deal was a $100 cash tip if we make our bus.” I explained that wasn't part of the agreement, but I would still get them there as quickly as possible. However, I reminded them that they promised me $100 cash no matter what.

She didn’t respond. As I began to pull into the NJ rest stop, I mentioned that I would be quick. I found a parking spot a few rows back from the entrance; it was packed. “Are you coming inside as well?” I asked as I put the car in park. “Maybe, not sure yet,” one of them replied. “Okay, I’m asking because I’ll leave the car running with the remote start.” They didn’t say anything in response. “I’ll hurry up but I’ll be right back,” I reassured them, still desperately trying to stay in their good graces, as I genuinely believed I could earn that tip.

At this point, it was foolish of me to think I would ever receive that tip—they were never going to pay. This was a lesson I was going to learn the hard way, one that would stay with me forever: always collect promised or negotiated cash tips upfront, without exception!

“Yes, hurry please. You’re going to make us miss our bus,” one of them said as I was getting out of my vehicle. What an ungrateful person, I thought to myself as I closed the car door and rushed toward the entrance of the rest stop. At that moment, I realized my mindset had completely shifted for this trip. I would no longer be positive and accommodating; instead, I felt bitter and disappointed.

As promised, I was quick in the restroom and returned to my car within minutes. However, as I approached my vehicle, I noticed neither of the women was there. It seemed they must have gone inside the rest stop, likely to use the restroom as well. With over an hour of driving still ahead to their destination, you could never be sure if there would be another opportunity to stop and go.

A few minutes went by, and I was shocked at how long they were taking, especially since they had complained about this stop delaying them from catching their bus. It was becoming clear that there was no way I could get them there on time. Glancing into the back seat, I noticed their belongings were still scattered everywhere.

What’s taking them so long? If I had known they would be going inside and taking this long, I would have grabbed a Starbucks coffee for myself. I was really craving a coffee since I hadn’t had my morning cup yet. Just as I was finishing that thought, they finally emerged from the rest stop with Starbucks in hand. Those mother fuckers! I thought to myself. They went from “we’re in a hurry” to “I’m going to treat myself to something.”

I felt incredibly disappointed but said nothing. Instead, I asked if they were ready to hit the road. As I backed out of the parking spot and left the rest stop to get back on the interstate, I thought that if I had the balls, I would have tossed all their shit into the parking lot and just left. I should have abandoned these ungrateful bitches at the rest stop. I pictured myself driving away, laughing as they ran out, yelling and screaming from a distance while I sped off without them.

But no, I was too timid back then and loved to torture myself. So there I was, speeding down the highway with these ungrateful women still in my backseat. And it was just a few minutes into driving again that they had the audacity to suggest I should drive faster.. “I’m going 80 mph in a 65,” I replied with some attitude. “And I don’t feel comfortable going any faster than that,” I added, trying to be as firm and direct as possible.

They finally got the point and didn’t complain about my speed for the rest of the trip. They asked for some music on SiriusXM, and I gladly obliged, hoping it would shift the energy away from me. And it worked! The trip finally had some rhythm: we were cruising along, and they seemed like semi-happy and entertained passengers. The right music selection can truly transform the mood!

However, this pleasant moment didn’t last as long as I had hoped. Our smooth cruising came to an abrupt halt when we encountered standstill traffic just outside of NYC. There were signs indicating which bridge or tunnel would be the quickest route into the city, so I opted for the Lincoln Tunnel. Unfortunately, it took forever to get through the tunnel—about 30 to 40 minutes just to cover a few miles. This was exactly the kind of traffic I had anticipated around rush hour.

It was just a few minutes before 9:45 a.m. when we came to a standstill as we neared the Lincoln Tunnel. They noticed the delay and began complaining to each other about their options. “We'll just have to buy another ticket and wait a few hours until the next bus leaves,” one woman said to the other. This seemed to frustrate them, and they asked if I knew of a faster route.

Seriously? I told you all I'm not from here, and you think I can just teleport past this traffic? And it’s NYC for fucks sake—everyone in the world knows how bad this traffic is. I held back a chuckle at such a ridiculous question as I responded that I couldn’t. For some reason, these ladies were determined to catch that bus.

As we pulled up to the bus stop, they were very eager to get out of the car. Good riddance! I thought. Once I parked the vehicle, I turned around to let them know I would grab the luggage from the trunk, hoping it would help secure my $100 tip.

“Nice meeting ya’ll, and I hope you enjoyed the trip,” I said while retrieving the luggage from the trunk and handing it to the ladies, trying to wrap up the journey on a professional note as my last-ditch effort to secure that $100 tip. “I hope I earned that $100 tip,” I added, feeling a bit awkward and sounding like a little weak-ass bitch. “We’ll tip you through the app,” one of them replied dismissively.

At that moment, I realized I would never see the money for two reasons. First, they had promised to tip me in cash just for giving them a ride, but their story and tone kept changing throughout the trip. Second, they hadn’t ordered the ride; their “John” had. And their relationship with him had ended as soon as I picked them up. the moment I picked them up.

But I was in New York City, and I was determined to make the most of an unexpected trip to one of the most entertaining places on earth. The first thing I did was find myself a cup of coffee—I was well overdue for one. I recalled passing a Dunkin’ Donuts just a few blocks down the street, so I found a parking spot and walked over to grab a coffee. After that, I spent about half an hour sightseeing by exploring the area on foot.

I also took the Holland Tunnel out of NYC to do some sightseeing while driving. I followed the Hudson River Greenway, even stopping to park and walk along the river. I figured I might not know when I’d return to New York City, so I might as well make the most of the opportunity. And I was right; seven years later, I still haven’t returned.

I still needed to get to my 9-to-5 job, so I told them I’d be in after lunch since I had some things come up in the morning and took some unpaid sick time. On the way home from NYC, I jammed out to Audioslave and Army of Anyone. The traffic wasn’t too bad, and I managed to get home, change, and make it to work. To this day, that remains the longest rideshare trip I’ve ever taken, and I still haven’t received that one hundred dollar tip.