My Subhuman Ex-Girlfriend and Her Insane 1% Clown Posse (Part I)

Legal Disclaimer: While this post mentions actual people and events, the entirety of the post is meant for entertainment purposes only. None of the following statements are to be considered factual or true. I, David Friedlander, the author, place complete intellectual and legal burden of conclusions derived from reading what I have written upon the reader. Further, none of my statements are meant or should be considered legally binding or intended as a means to communicate with any person(s); further, the fantastic, deliberately ambiguous nature of my writing precludes any of my statements, including those statements in any and all linked posts, and those statements as they relate to my children, to be used as evidence for arrest or proof of my mental fitness, lack thereof, or any other legal proceeding intended to limit my ability to freely exercise my First Amendment Rights as an American, writer, historian, researcher, seeker, and — above all else — a storyteller. I have a decade of notes showing how I use the written word to make sense of the world, hoping that inquiry has relevance for those who choose to read what I write. TLDR: I’m just telling my too-fantastic-to-be-real stories. Truth is in your Court.

There are dangerous creatures at large. Many of them look like people, but they are not. I pray this post disavows this misconception. 

These creatures can be detected mainly by their tools: BMWs, mansions, golf clubs, fresh dye jobs and blow-outs, and their perpetually-new clothes with discrete labels to indicate their bloated prices. These creatures have become so parasitic, consuming so many natural resources, letting so many real humans die rather than share, they have reversed millennia of human evolution. They can no longer be classified as humans, but as some bipedal humanoid subspecies. 

Homo insatiableus? Homo vulgarus? 

This story concerns one of these creatures —one I regrettably called my girlfriend for two years. She responds to the name “Josslyn Shapiro.” If you’re in Park Slope, Westchester, or northwestern Connecticut, her main habitat, approach Josslyn with extreme caution. 

I found Josslyn in Prospect Park in 2017. We were riding the fifteen-mile route of the Transportation Alternatives Century with our young children, my two to her one. Her name was almost identical to an ex of mine and her son and my youngest shared a unique name. It seemed like kismet. 

Like me, Josslyn was a long and lean humanoid, likely a few years my senior in her mid-to-late-forties. She gave me a few looks from behind her dark sunglasses when we were waiting for the ride to begin. I wasn’t unresponsive. She had a SOMA touring bike — the exact type of bike I had in my search engine. She disappeared for the ride, claiming later her son punctured, forcing a detour to the bike shop and a solo run of the route behind the main pack. I chatted her up at the Central Park finish line, where she was meeting some family members. 

The fateful day in Central Park, post ride.

I exchanged info with Josslyn and one other parent, a head editor at Vice. We all met up for a bike-playdate the next week in Prospect Park, which led to another playdate without the other parent at my cave, and finally a date without the kids in the Slope.

On the date, she told me she had a Environmental Sciences PhD from my alma mater, Columbia. She had pulled ice cores in Alaska and was born on Earth Day, supposedly. She had served as the Deputy Director of Environmental Services under the Bloomberg Administration, with a focus on environmental remediation for Superfund sites like Newtown Creek and the Gowanus Canal, the latter of which was not far from her northwestern-Park Slope coop. 

The million dollar playdate.

When we met, I was on year one one of a divorce and she on year three of a personal and professional pause following the death of her husband Evan Shapiro, a well-known and practicing urban planning professor and consultant specializing in the large, capital-intensive, public-private-funded civic urban projects. Evan had been dealing with cancer-related issues for years. Despite his general ill-health and her apparent sterility, likely exacerbated by their harried lifestyles, they tried their utmost to conceive. Their one son was born after they had just given up on years of painful, expensive IVF treatments. The son was a baby when Evan went into the cancer tailspin. The child was four when it eventually killed him.

She had spent a year or more writing a memoir about her experiences with nursing her husband. She planned to be an author and had friends who were willing to publish it, but ultimately decided she didn’t want people to know about her personal life and scrapped the plan. 

Her main focus, she told me, was taking care of herself. She was putting her and her son’s needs ahead of supposed societal or economic obligations, much to the consternation of her family. Her days revolved around her son’s needs and hobbies, errands, and experimenting with self-care regimens like light weightlifting and healthy eating from the Park Slope Food Coop. She told me she never took care of herself before and it was time. 

The people she spent the most time with were millionaire moms from her son’s then-school, the Seaport’s Blue School, and their play-dates and other kid-focused activities. She occasionally mentioned good friends from her Northwestern undergrad career, but I only met one, briefly. Most of her time was spent alone, doing independent activities with her taciturn, athletic son, or with her family who lived north of the city in Westchester and Connecticut.

In her, I would find interpersonal and physical shelter from the assault I was undergoing in the King’s County Family Court. Her modest but homey walkup coop—a mile from my Spartan, one-bedroom, man-cave in Windsor Terrace and a block from the Food Coop— provided the tranquil domesticity I longed for. She gave me a place to rest after taking care of my two active boys by myself or hanging out alone for way too long in said cave. 

Far cooler in temperament than my previous exes, Josslyn provided the conditions in which I could regain my capacity to trust and communicate with women. She seemed bright, classy, self-aware, and, unlike a lot of NYC women, had time to hang out. Her single-mom schedule worked well with my single-dad meshugenah schedule. Four years my senior, she wasn’t bothered by my age or marital status —both of which made me nonstarters for younger women. Though a bit straight for my liking, our story worked. We dove in fast. 

Meet The Granthams (aka Shapiros)

I met Josslyn’s family not long after we started dating. She invited me to Connecticut for Thanksgiving, 2017. There was a Friday dinner at her half-sister Skylar’s place in Washington Depot and we would hang and stay nights with her dad, Ira Shapiro, and stepmom, Jackie Dedell not far away in West Cornwall. 

I spent Thanksgiving day in New York City. I took Josslyn and the boys to see the Macy’s parade at a party at a Ratner-owned Central Park West apartment. Later that day, my boys and I did Thanksgiving dinner with my cousin Liz Goodman and her family at their Fort Greene townhome. I dropped my kids off with their mom that night. Josslyn, her son, and I headed north the next morning. 

On our way to Connecticut, we stopped by Josslyn’s mom’s place in her hometown of Edgemont, New York. Though previously unknown to me, Edgemont is the well-appointed sister-city of ultra-rich NYC-commuter suburb, Scarsdale. To some, Edgemont is viewed as the quieter, classier side of the tracks. Her mom Barbara was Cheryl Teague’s longtime assistant and lived there with her second husband of many years, David, aka Bubby, a bald as a bat, former-IBM executive octogenarian and current Porsche and antique watch collector.

Barb and Bubby’s stolid, ivy-covered, faux-Tudor home, and their bagel-and-lox-familiar form of UWS-Jewy arts-and-politics conversation were my last contact with anything resembling reality for the weekend. 

The country north of Westchester and throughout southwestern Connecticut is some of the world’s best. We drove Josslyn’s BMW wagon on quiet, perfectly-paved roads through poetic little New England towns and low, rolling mountains that are covered in life-giving trees much of the year but passed by us in seasonally-appropriate bareness and solemnity. 

Arriving at dad’s place meant turning down a tiny forest road inlet with little more than a standard mailbox to indicate its existence. After one mile on the road, one pulls up to the “grounds.”

The first thing I said upon viewing it was, “I didn’t know your dad was Lord Grantham.”

Tune in soon to learn what happened and the colorful cast of ghouls I met that weekend in Connecticut.

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