Two Rides, a short story written by James Dean Collins at
Vladimir Proskurovskiy

Two Rides

Two Rides

written by: James Dean Collins



Nearly four years ago, the two major rideshare companies that operate in the United States touched down in Philadelphia and have stamped their influence on the tri-state area ever since. There was a small outcry and backlash at first, but predominately there was a lineup of people desperate to find work in the new gig-conomy. I know this firsthand. My introduction to the startups was as a Brand Ambassador.
I won’t say which company I worked for in signing up new drivers. That doesn’t matter, and I’ve actually worked for both companies doing that job at this point in my life. The important thing is that in July 2015, my position as a brand ambassador ended, I was laid off, and with that, I went to work for the same rideshare company as a driver. That’s what the gig-conomy directed I do, as hourly positions were going by the wayside in the mid-Atlantic.
Some four years later, I still drive rideshare. There are times I had to do it as a primary source of income, and times I had to do it to supplement whatever else I was doing for money at that point in time. I’ve taken over 1,600 rides in that span. That’s actually not a lot, by driver’s standards. I’ve met rideshare drivers that have taken as many as ten thousand rides in a year-and-a-half span. Very likely, there are more in the area with greater numbers.
Every ride is the same, and different. The patron is almost always different, but the protocol is always the same. I’ve had good rides; I’ve had bad rides. I’ve received big tips from people, and I’ve had people screw me over by canceling upon reaching the destination. But, the work is flexible, and it’s nice to know it’s there even though the pay is poor.
The following stories are true. This is an account of two different rides I had at the end of March 2019. One was on a Friday night, and one was on a Saturday night. Both were men in their late 30’s, both had been drinking, and both had been in the military. That’s where the similarities end, in my opinion. At least, that’s where the similarities that I can confirm ended, based on what they told me. The dialogue will be paraphrased, as I was not recording them. I will give my opinion on these stories. The events are not a dramatization. The names will be changed for the sake of anonymity.

Robert was a Latino man of age 38. He had long hair and an incredible beard. By his own admission, Robert was a drinker, but he told me it was for the fun of it. He entered my 2004 Dodge Caravan, a vehicle I cannot stand by the way, on time and ready to head to the Maryland border by way of Chestnut Hill where I picked him up.
“Hey man!” he shouted at me in a friendly, bellowing voice. “Can you do me a favor?”
I shrugged. I’m pretty easy going when it comes to driving rideshare. As long as it’s no open containers or anything I can be arrested for, I let the rider do whatever they want.
“Well,” Robert continued. “I need to go to the Shoprite (grocery store) and Brookside Liquors. I mean, is that okay with you?”
“Sure,” I told him in return. I don’t mind waiting at stores. The meter runs, so to speak, but I don’t earn much more by waiting. Nevertheless, it’s a chance to be alone with my thoughts.
He smiled at me. “Cool, man! So how has tonight been for you?”
I shrugged, eyes on the road. “It’s been okay. Just kinda got started a moment ago.” It was my standard answer for riders and usually the case. I don’t mind talking to people when I drive; I also leave them alone if that’s what they want.
“Wow,” he responded, shifting in his seat. “Thanks for waiting for me over here, by the way.”
As we pulled into the shopping center, the lights at the liquor store were turned off, which was strange for that store. Usually they stayed open until one in the morning.
“Aw man,” he said. “Why are they closed? It’s a Friday night and it’s only 9:30!”
I shook my head as I approached the grocery store. “I’m not sure, but there will be other liquor stores on the way to Elkton. (Elkton is the city in Maryland that borders Newark, Delaware.)
He laughed. “Thank you again, I appreciate it!”
I pulled up to the entrance and threw my blinkers on. He got out, told me he’d be right back, and I waited there for him with the pop radio station as my company. I don’t like modern pop music, but being as the station is in Wilmington, it’s typically the only radio station my Caravan will pick up and hold while my phone stays plugged in to maintain the battery.
And so I waited for Robert.
And I waited.
And I waited.
Right around the time a Panic! At the Disco song started, he came back out with about six shopping bags and made his way to the passenger side door of my van. I tried to help him with the bags as he got into it.
“Sorry man,” he started. “I swear, I was looking for this thing, and went up and down the aisles, and just couldn’t find it!”
“It’s okay, Bobby,” I told him as I pulled back out to the road. “I got nothing but time.” I wasn’t lying, either.
“I’m gonna go over to my new girl’s house tonight,” he told me. “I’ve been with the same girl for 15 years, and this week, we’re just done.”
“Sorry to hear that,” I replied in earnest at a stoplight.
“Eh, it doesn’t matter, I guess,” he said back. “It’s just funny how life works.”
With that, he began with his back-story. I never solicit any details from a rider’s personal life, but more than a few times they’ve given them to me.
Honestly, I prefer a cash tip. But what the hell, I’ll take life advice too.
“She’s got kids, this new girl,” he began. “I don’t like kids, I’ll be honest. Actually, that reminds me, do you smoke weed?”
I get asked that question a lot, actually. The answer is yes, every now and then I do. However, I never do it while I’m driving, especially not rideshare. I answered Robert as such.
“Oh,” he replied to me. “Well, is it cool if I do it? I have a pen.”
“Sure,” I responded. Robert wasn’t the first rider to smoke weed in my van, and won’t be the last, either.
He bellowed a laugh. “Thanks man, you’re one of the good ones!”
With that, he produced his pen and took a deep puff, then continued his reflection.
“But this new girl,” he said. “She has a big ass, and I like that.”
I kept my poker face as we drove towards Maryland.
“I got problems, man,” he said, not needing my verbal acknowledgement. “I’m in this car right now because back in September, I bought a brand new Jaguar. By November I wrapped it around a tree. I realized I needed to do a few things after that, you know?”
I nodded as I kept my eyes on the road.
“I went to rehab, some clinic up in Bucks County (PA),” he told me as he solemnly reflected on his mistake. “Thank God no one was hurt, but for the first time in my life, after 38 years, I saw a therapist, and it helped a lot, you know? I seem like I talk a lot, but I actually just keep a lot of my shit bottled up.”
He took another puff from his pen and continued.
“I got daddy issues, James,” and he said it to me, just like that. “I hated my old man. The last time I saw him, I beat the shit out of him. Then I turned around and joined the fucking army.”
“Really?” I asked him, half trying to pull my side of the conversation, and half wanting to hear about his time as a soldier.
“Yeah,” he said. “They offered me ten grand to sign up, so I took it and got the hell out of my house. I did eight years with them. It’s funny how that works. But, I didn’t have to deal with my dad anymore.”
In retrospect, that’s interesting to me. I find it incredible that a man would choose to actively gamble on his life for eight years as opposed to living with a father he hated. I find it brave, frankly.
We crossed the state line and the liquor store on the corner, Caps and Corks, was still open. I pulled into the lot and he got out gleefully.
“I’ll be right back, James!” he happily shouted. With that I watched him run into the liquor store as I sat in my minivan with the meter running.
He came out a few minutes later with a black shopping bag. When he got in a sat down, he almost immediately produced a small bottle of Seagram’s gin and started to drink it right from the bottle.
“Sorry,” he said to me between pulls from the bottle. “I have to drink this before I get there. She doesn’t want me drinking.”
I pushed the guilt down and ignored my open container rule as we started down the last stretch of highway to his girlfriend’s townhouse.
“Do you think she’ll smell this?” Robert asked, sticking the bottle towards my nose. But, he fumbled the bottle, and it spilled onto my floorboard.
Of course he spilled the gin in my car. I deserve that bit of karma for letting him drink it in there in the first place.
“Shit, man!” he cried out, rushing to dry it up and put a cap on the bottle. “I’m sorry!”
Being the enabler, I tried to reassure him. “It’s cool man,” I replied. “I’ll dry it.”
We pulled up to the building and he finished off the last of the gin.
“Hey, thanks James!” he told me as he left my van. “Have a good night, alright?”
And he gave me two bucks.
What would I have said to Robert if I could’ve shared freely, without concern for my terms of service contract?
I would have told him honestly that he’s doing the best he could, and that it was admirable that he was still going as he was in life. Sure, he did something terrible in drinking and driving, but while the outcome could’ve been far worse, it woke him up, at least. I think it’s admirable that he sought therapy, even at this point in his life; it’s never too late to start working on us.
Hopefully, he quits the hooch some day.

Now it’s time I brought up the ride I had on Saturday night. I got a call late, at about 11 p.m., in Glen Mills, PA. The end of the route was a long, winding back road with no streetlights on it, of course. My van gripped the curves in the road as I made my way towards a large, three-story house tucked away in the woods.
Again, I’m protecting the name of the person who called for the ride. It was a young woman that I would place in her early 30’s. I’ll call her Tara. Tara was the owner of this massive house in the woods of Pennsylvania, actually. She met me at the foot of her long driveway. She wore a jogging outfit, and greeted me at the door of my minivan.
“Hi,” she said. “Sorry this is taking so long. He’s coming.”
There was a loud noise and a grunt behind her. She whirled around suddenly and ran back up the driveway as I waited with the passenger side door open for her.
Moments later, she was helping a big guy, about 6’3” if I could estimate, down the rest of the driveway toward my van. At one point the guy, let’s call him, Steve, threw her arm from off his shoulder and stumbled the rest of the way to my passenger seat. He shut the door as she leaned into my window and told me, “Please make sure he gets home safe. And try not to take what he says too seriously.”
Steve then shut my passenger door and we were off.
“Man,” he began with me. “Can you believe I f*cked her?”
Of course he broke the ice with that.
For the next hour, I tried my best to stay out of this horrible, asinine conversation like I always do with horrible, asinine conversations. With the way this guy was though, that proved impossible.
He first asked me if rideshare was my full-time job. I responded honestly and I told him, “no”. He then went quiet as my phone blurted out a notification.
“Please make sure he gets home, safe,” the female robot voice blurted out from my directional app. “I’ll be sure and leave you a big tip. (She did, to be fair. It was $15 dollars if I remember correctly.) And I really don’t want to deal with him the rest of the night.”
See, when a rider contacts a driver through this particular rideshare app, the text message will either sound out verbally over the phone or through Bluetooth speakers. So this guy, Steve, heard everything his…girlfriend? Well, whatever she was to him, Steve heard everything she actually thought about him through my phone speaker.
“Wait, what was that?” He asked me in a drunken slur.
“Nothing,” I told him. I pulled over immediately and texted her, “he can hear everything through the speaker. Try not to text again.”
I received nothing back.
We continued driving now, and he continued with his life story.
“Yeah, f*ck her,” he responded. “Hey, do you know I f*cked her? Do you know who she even is?”
I shook my head “no” and kept my eyes on the road.
“Man,” he continued. “That’s the assistant to the state (government position withdrawn for anonymity)” he replied. “She wanted me to come over but I’ve been drinking all day, so I made her call me a rideshare. Can you believe that?”
Again, I shook my head.
He grabbed my arm, which made me jerk the wheel a little, of course. At this point we’re cutting through the town of Brookhaven in Delaware County.
“Man, I asked if you could believe that or not?” he begged an answer.
“No,” I responded flatly. “No, I don’t believe that.” And he let go.
“Where are we going, anyway?” he asked; now favoring his ribs. “I think I bruised when I fell. Sh*t.”
“She wanted me to take you home,” I replied. I checked the app. “We’re going to…New Jersey.”
He shook his head exaggeratedly. “No,” he replied. “Sugarhouse (casino) I want to go to Sugarhouse.”
I shrugged. “Okay, Sugarhouse it is.” It’s impossible to miss Sugarhouse, frankly. It’s now a Philadelphia landmark. I’ve had a number of pickups and drop offs from that casino.
“You know what I like to do?” he asked. I nearly replied, “Ask strangers questions about yourself that they can’t possibly know the answer to over and over?” But, I stopped myself. I didn’t need him grabbing my arm again while I was driving.
Spoiler alert, he would grab it anyway about two or three more times.
“I go into the poker room, okay? I take like, $500 dollars. And then, I fold like, the first ten hands. Then I just start on a tear. Hey, do you have $500. If you do I can make you like five grand tonight.”
“I, I don’t have $500 dollars,” I responded. I mostly didn’t believe him but I’m also poor and sometimes I get desperate enough to where I might buy the proverbial magic beans anyway.
He scoffed at me and grabbed my arm, again. “Of course you don’t. Do you know what I do for a living?”
I shook my head “no” yet again in response to this stupid game of importance he liked to play.
“I run a remodeling company,” he began, and then he thought to himself for a moment. “Well, it’s actually my dad’s remodeling company. He had a stroke and I’m overseeing it.”
I felt some empathy for Steve, empathy that would fade about as quickly as it entered my mind. We pulled on to I-95 at this point in the journey, by the way.
“When I got out of the Marines, though,” he continued. “I used a VA loan to buy my first house that I rent out now. Do you know how many units I rent?”
I just sighed. “I don’t know, twenty?” I asked sarcastically.
“Twelve,” he responded frankly. “Twelve buildings, all in Camden (New Jersey, a city under…redevelopment (attempted gentrification)). And I do all of the maintenance myself. I make money hand over fist! What’s your credit like?”
“Um,” I started, a little taken aback. “Barely north of 500?” That wasn’t a lie, by the way.
He scoffed again. “Are you kidding me? Do you want to drive this shitty van for the rest of your life?”
I didn’t respond to that.
“That’s the thing, man,” he went on. “We’re two white guys in our twenties. Do you know what we’re entitled to? It sickens me that you can’t get a loan but all of these n****** and Mexicans get all of our damn money and shit.”
And with that, the slumlord revealed himself to be a casual racist, which was of no surprise to me.
We were close now, almost to exit 20, thank God, which is the Penn’s Landing exit. The casino was about another 15 minutes away.
“You know who else I f*cked?” he seriously asked me as we made our way down the off ramp.
I didn’t even dignify him with a response this time.
“Miss Delaware, 2005,” he responded to himself. Great, that was all the more reason to not be proud of my home state.
We pulled off of I-95 in thankful silence as I drove us up Columbus Boulevard.
I drove up to the poker room entrance and I opened the door for him. He stumbled out and looked back at me.
“Are you sure you don’t want to come in?” He asked. “You can be my personal driver for the night. I’ll pay out of pocket.”
“No, thank you,” I simply responded. “I’m actually done for the night.”
He gave me a “f*ck off” gesture and continued inside. Before I marked the ride as complete, I texted her to let her know that I dropped him off where he wanted to go, and that I was ending the trip.
And I did, and that was my night.
So, what would I have told Steve if I could have been candid with him?
To start with, I would have told him to quit grabbing my arm while I was trying to drive.
The second thing I would’ve done would have been to kick him out of my car on I-95 for that racist garbage he spewed. It’s those government programs that allow people to be the tenants in his slum buildings in a poor neighborhood of which he takes advantage.
Landlords like him, in my opinion, have always tried to manipulate the rental market so they don’t have to do any real work. I’ve seen this firsthand in Philadelphia.
Most landlords got into the business so they could do the least amount of work that they can in life and still feel like a big shot. Granted, there is work to do when a person manages property. Zoning and business licenses must be squared away in the city, as well as proper access to emergency maintenance and communication with tenants.
But those things are always, always done out of necessity. Only one property manager I’ve ever met (and I’ve met more than a few) actually got into the rental business out of passion, or wanting to create a great experience for a renter.
Finally, I would have told Steve that I pitied him. Yes, I pity Steve.
Steve has money. He’s younger than I am. If he drives, he has to have a way better car than the thousand-dollar van I’m driving at the time of this article. If not, he can afford to take rideshare (or have others call him a ride for him) during peak hours on the weekend. He’s in charge of two companies. He can recreationally gamble.
I’ll be 36 on September 13th. I have something that Steve doesn’t, and I didn’t know I had it for a long time until I met him. For 35 years, I had no idea I held the secret of life, all along. And I guess for the rest of my life I’ll owe him for teaching me something critical about myself, and he has no idea he did it.
I pity Steve because I am loved, and he is not. At least, he doesn’t think he is, subconsciously. I don’t know anything about the guy. Well, I don’t know anything HONEST about the guy. I don’t know what his family was like, other than he seems to resent his father. I can make assumptions as to his psyche, which seemed fairly fragile, as well as what he’s like as a landlord based on what he told me in a drunken, racist tangent.
But based on his activities that night, which consisted of excessive drinking and gambling, and his desperate need to convey how great he thinks his life is to a stranger trying to earn an honest buck, I can personally assume that Steve has a hole within himself. Psychologically he feels very inadequate, and tries to fill those holes with excess and symbols of status.
He looked down on me as a person, based on what I do for money and the car I was driving. But at the same time, he desperately tried to bond with me. I’ve had plenty of drunken white guys in my car (mostly college kids) and they don’t say a thing to me, which I’m fine with. Maybe if they’re friendly they’ll tell me about a trivial problem in their lives, such as a new boss they don’t like. But the conversation never runs as deep a gamut as Steve’s did.

So, what did we learn? Two men who are surprisingly similar couldn’t be more different. Both were ex-military, both were in their 30’s. Both of them were excess drinkers who also loved sex.
But one was still trying to find his way in this world. He didn’t look down on anyone. He was appreciative of his life, and trying to get help for himself.
The other was desperate for respect, attention, and status. Unless he had something to gain from a person, they weren’t worth his time. At least until he hit bottom and realized he was alone. He also built his life on the backs of others, others who he looked down on because of their skin color.
I hope you found the stories of Robert and Steve interesting on a case-study level. I certainly did. But, as quickly as they entered my life, they were gone.
They were nothing but two rides, after all. And I have quotas to make.



One of the most frequent questions I get when driving people around is, “What’s the worst ride you’ve ever taken?” Believe it or not, it wasn’t either of these two rides. It was a ride on July 4th when I first started, driving a family from Independence Hall to Wayne, Pennsylvania.

They demanded I drive 90 mph in a Jeep Cherokee with their children in the back.

Oh, and this story is dedicated to my dear friend, Star, who makes me a better person every day and has always supported my work.

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