Hitchhiker Chronicles

Comic scene: “Huh? A ride to the train station? I’m just the trivia host, mate...” “Excuse me, I know this is a trivia night, but is there a way I can get a ride to the train station? My Uber canceled!” Signs read “TRIVIA NIGHT!” and papers read “ANSWER”; sound effects say “BUZZZ!”, “CHEER!”, and “MURMUR.”
A trivia host tries to help a stranded guest reach the train station during trivia night.

Another WordPress writing prompt from August 2026 that I saved for this 30-day challenge. Question: What’s the weirdest coincidence you’ve ever experienced?

There is a massive neon sign invisible to the naked eye that must be tattooed directly across my forehead. It doesn’t say Welcome, and it certainly doesn’t say Sensible Adult. No, it clearly reads: Designated Shepherd of the Lost, the Confused, and the Mildly Terrifying. I have a fatal flaw. I possess a heart entirely too big for the Mid-Atlantic region, paired with a dose of Catholic guilt to prevent people from accidentally orchestrating their own demise.

Take, for instance, a rainy night at Stan and Joe’s in Annapolis back in 2024. I was hosting trivia, a respectable side hustle, that requires intense focus, reading comprehension, and the ability to ignore drunk people arguing over the capital of Nebraska. ( The Capital of Nebraska is Lincoln.) Enter a woman from the Northeast with a dream, zero grasp of Maryland geography, and a plot straight out of a low-budget indie thriller.

Between my trivia questions, she casually announced she was taking “the night bus” to Washington, D.C., to finalize paperwork on a house she didn’t want to live in. In a torrential downpour. From downtown Annapolis. At 8:00 PM. Now, anyone with a single functioning brain cell knows Annapolis public transit clocks out when the sun goes down. (I have been schooled that their transit system does not clock out at sundown, but it does not head to DC.) There is no magical night bus. No secret subway tunnel links historic dockside pubs directly to the Washington Monument. When I broke the news that she was stranded, she looked at me like I had personally canceled the transit grid. Naturally, her backup plan was to “just catch the train.” Honey, what train? I thought to myself, my left eye starting to squint.

Because the universe decided I was her court-appointed guardian angel, I had her call her friend and verified she wasn’t completely hallucinating a friend who lived in DC. Once verified, we struck a bargain: wait until I finish yelling about pop culture to the midshipmen and millennial players. I would drive her all the way to Baltimore Penn Station so you can catch an Amtrak to DC.  She agreed, and since the rain still hadn’t stopped, it was a decent deal.

Did she wait quietly? Absolutely not. While I was on the mic, she peppered me with her entire lifetime backstory, eventually announcing, unprompted, “You know, I’m a Libertarian.” Pulling out her pocket-sized Constitution.  Ma’am. I am reading a question about The Golden Girls. I do not care about your stance on America’s fiscal policy; I care that you don’t freeze on West Street.

I finally loaded this mysterious runaway into my car. I thought to myself: Was she an undercover spy? A time traveler? An alien seeking safe passage out of Anne Arundel County? Was a black SUV full of syndicate hitmen pulling up to the bar ten minutes after we left? The drama my brain created was better than any Netflix drama. I navigated construction traffic, listened to a podcast-worthy monologue about her existence, deposited her safely at Penn Station by 11:00 PM, and sped off to pick up my mother from work, wholly accepting that I am a giant sucker.

That was Hitchhiker Number One: a woman who weaponized sheer helplessness.

Hooded pedestrian standing in a rainy street viewed from inside a car
A driver watches a hooded pedestrian through a rain-streaked windshield on a neon-lit street.

Hitchhiker Number Two, however, skipped the paperwork and went straight for vehicular assault.

Cut to a recent evening on Edmondson Road out in Beltsville. For those unfamiliar, this is not a well-lit suburban boulevard. This is a narrow, twisty, ditch-flanked road cutting through farmland. It screams mystery episode.

I’m driving along, minding my own business and stressing about closing out tasks before starting my new job, when a man materializes out of the rural ether. Work boots, blue jeans, silver-white hair, a blue Haines T-shirt, and the pièce de résistance: a crinkly white plastic grocery bag.

He didn’t stick his thumb out like a polite 1970s nomad. He stepped into the road and aggressively lunged toward my moving vehicle, eyes locked on my door handle with the absolute determination of a zombie who missed the last commuter rail. He was getting in that car, with or without my permission.

I don’t have the calendar availability to get murdered on a country back road. I slammed the gas, violently swerved away from him, nearly pitched my entire car sideways into an agricultural ditch, and peeled out like an extra in an action franchise. The windows went up immediately.

So that is where we stand. On one end of the spectrum, I am a freelance chauffeur rescuing wandering souls from their own logistical ignorance. On the other, I am evading ambush attacks in the Beltsville brush.

I’ve since adopted a strict self-defense mechanism: I keep the passenger side of my car littered with enough junk that offering anyone a seat is physically impossible. My windows stay up, my doors stay locked, and my inner bleeding-heart Samaritan has officially clocked out!

If you would like to donate to the hitchhiker prevention fund à https://ko-fi.com/chemichelletales

I have another one I will post in a few days.

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