Sometimes You Hop in the Car with a Stranger

Sometimes you have to break up with your dentist. Not because of anything they did or didn’t do, but because your health plan changes and naturally, well, you just kind of drift apart.

It’s a situation that shouldn’t be stressful at all, but since I am the king of turning the simple into sizzles and haven’t been in a break up scenario in six years, I made sure to handle this as awkwardly as possible.

Awkward meaning I called the lady at the front desk to end things and five minutes later called what I thought was a different dentist’s number to schedule an appointment. I heard her typing on the keyboard. Little bit of silence. “Mr. O’Brien, didn’t you just call to cancel with us?”

Shaky break up behind me, I was ready to try out a new dentist. Went in, and I did a little too well. Given my diet, specifically the late night Oreo milk baths, at least one cavity per six months seems like a pretty fair pace. An admirable goal really. So to be told zero, Zero? I almost made him go back to the x-ray machine.

My concern was this being some sort of bait and switch. Build up my confidence, make me feel like I’m invincible, get me to take a few nights off from brushing, up my Oreo intake, then bam hit me with seven cavities and a root canal six months later.

But on the December night of this story, I wasn’t thinking about the dentist or teeth or anything other than, “I’m hungry and I know it’s 11 o’clock but I want a Tenderizer.”

The Tenderizer may be the best sandwich in Chicago. And let me rephrase that, it IS the best sandwich in Chicago after 10 o’clock. Think grilled cheese sandwich on Texas toast but with chicken tenders, bacon, hot sauce, bbq sauce, dip that baby in ranch, the Tenderizer is perfection. The quintessential late night meal, available at Cheesie’s on Belmont, which is kind of walking distance from my apartment.

Not walking distance in the winter. And that’s ok because the 77 bus is essentially the Cheesie’s Express. I looked down the street and saw the 77 two lights away. I checked on my phone for the next one, arrival time was 19 minutes. It was now or never and I wanted that sandwich.

I broke into a sprint for the first time in months, especially hard to do in boots. My lungs immediately said, “Alright, screw this.” I kept pushing, I had the voice of our high school strength and conditioning coach in my head, “The pain of regret is going to be worse than the pain you’re feeling right now. Dig deeper! Go, go, go!”

I caught up to the back of the bus, I put my hand in the air, the light turned green, I was so, so close, but the bus started up again and I had lost. I stopped at the edge of the curb, hands on top of my head, trying to catch my breath. It was over. Time to turn around and head home. Go to sleep on an empty stomach.

A black Lincoln pulled up to the curb. Passenger side window rolls down.

“Need a ride?”

First instinct of course was to say no. Years of “strangers-are-the-enemy” talks in elementary school prepare you for this exact moment.

But… the Tenderizer.

I looked in and the driver seemed like she was about 60-65 years old and the man in the passenger seat looked to be around the same age. Seemed safe enough. I walked to the back door.

As I reached out for the door handle, the strength and conditioning coach in my head had been replaced with my mom and my wife’s voice, “Are you kidding me?! Chris, turn around right now!”

Too late. Door closed. I was either going to Cheesie’s or going into some storyline for a future CSI episode.

I scanned the backseat for any red flags. Blindfolds. Hatchets. Chainsaws. Found nothing. Just a People magazine on the floor, which that’s about as innocent as it gets. The radio was on a religious station. They asked me about what I did for a living, kept the car at a comfortable 73 degrees. This was the definition of a pleasant car ride. There was nothing strange about these strangers.

I still kept waiting for the made for TV moment. When were they going to pull off these incredibly realistic looking masks? When do I get hit from behind with a baseball bat? When are they going to toss me out in Lake Michigan?

We pulled up to Cheesie’s and I thanked them for the ride, wasn’t sure if I needed to pull out cash or anything.

“Hey, are you looking for a dentist by chance?” the driver said.


“Actually, I kind of am,” I said.

“Well,” the driver said. She gestured to the man in the passenger seat. “His office is right in this area. Here let me give you a card.”

Is hopping in cars with strangers probably still a bad idea? I guess so, but if you stick with that strict rule then you never end up with a story like this. Then again you also never end up as a story on the 11 o’clock News, so it’s a tough call. 

I’m just happy you came by the blog and to celebrate, why not type your email here in that box below and I’ll send you a Medium Rare post every week. What are some future posts you ask? This week I’ll have a pro tip for frozen pizza cooking. Next couple weeks: A way to figure out if you have a stomach flu or just a bad meal. And then some Chex Mix Etiquette. Whew, if that doesn’t get you excited to subscribe, I don’t know what will! And if you can’t wait for all those, enjoy some semi-controversial stuff on escalators and beanless chili.

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