The Time I Drove My Drunk Property Manager

Having spent my entire life in Delaware—40 years and counting—I always figured that one day I’d end up giving a ride to someone I know while driving for Uber or Lyft. With our state being so small, it felt like the odds were stacked in my favor. After all, we’re all just a few degrees of separation away from each other in this small state!

After completing thousands of trips, I finally gave a ride to someone I knew. But it wasn’t the experience I had imagined. I didn’t run into an old high school buddy I hadn’t seen in years, an ex-girlfriend with whom things ended poorly, or a former coworker who used to drive me crazy.

Nope, it turned out to be my current apartment property manager!

It was a typical weekday morning in Wilmington, Delaware with the usual hustle and bustle of people heading to work. It was still the post-pandemic era, meaning that rush hour wasn’t as chaotic as it used to be, but as rideshare drivers, we were still required to wear masks.

However, many passengers didn’t adhere to the guidelines and barely wore masks. And when they did wear masks, they often treated them like mere accessories, draped around their necks instead of covering their faces.

As my apartment manager approached my car without a mask, I immediately recognized her. While I quickly connected the dots as she got into my vehicle, she had no idea who I was behind my mask!

“Caroline?” I asked, a bit taken aback. “Yep,” she replied, sounding sluggish and a little under the weather. Although my voice was familiar, she had no idea who I was. It’s pretty surprising, considering I’ve spent months complaining in person and through email about my neighbor throwing parties and smoking weed. Clearly, she hadn’t bothered to check out my Uber profile!

She got into my car looking like she’d just pulled an all-nighter, and the strong stench of body odor, alcohol, and cigarette smoke was almost unbearable. It was so intense that I could practically taste it—and trust me, it was disgusting! Plus, it was nearly time for her to start work at the leasing office, where she typically arrives before it opens at 9 AM.

“VFW?” I asked, confirming her drop-off spot.

I had picked her up at a row home in downtown Wilmington. I thought maybe that was where she lived. However, instead of heading to work or running an errand, she was on her way to a private bar.

I was somewhat confused since it was still early in the morning, and bars in Delaware usually aren’t open at that time. I figured she might have the day off and was getting dropped off near another location she needed to visit. And she still had no clue who I was!

“I’m exhausted,” she said with a yawn, beginning to share what happened the night before. In her late 50s, I never would have guessed that she spent her weeknights partying like someone in their 20s.

“Oh, yeah?” I replied, hoping to get her to share more. But with just a five-minute drive, I didn’t have much time to gather all the details.

“Yea, I left my car at the VFW last night. Got to retrieve that then go home and shower off last night,” she just openly admitted without any guilt or shame. 

I always suspected she had a drinking problem since I’ve seen her drinking wine in the leasing office. And this entire interaction proved my suspensions right!

And from what I gathered happened the prior night is that she hooked up with some veteran dude at the VFW and spent all night up with him. She had noticeable dark circles under her eyes and looked like she was struggling as she got out of my car.

But don’t worry, your secret is safe with me—that is, until you raise my rent, then I might have some leverage to work with!