Obsession on the Upper East Side

Book review: You All Grow Up and Leave Me, by Piper Weiss

In this Gossip Girl meets true crime hybrid memoir, the story of Gary Wilensky, private tennis coach to wealthy Manhattan teenagers who made a thankfully unsuccessful abduction attempt of one his students, is recounted alongside the author’s growing pains. She had been his student too.

In spring of 1993, Wilensky tried to execute a thoroughly planned abduction of a former student, a teenage tennis player from an Upper East Side prep school. The attempt is brief; as disturbingly prepared as he was for after the kidnapping, he was disorganized and panicky when actually setting it in motion. Shortly after, he committed suicide, and the entire event blew up into a media firestorm, especially after his video-monitored, kidnapping-modified upstate cabin stocked with hostage supplies, sex toys, and pornography was discovered.

Chapters about what was uncovered or learned about Gary’s life and possible motivations intersperse with those of Piper’s life, then and now. Back then, she was enduring the common awkwardness of adolescence coupled with the unique experience of being a wealthy, privileged Upper East Sider. And if I’ve learned anything from the documentary that was five seasons of Gossip Girl plus all the books (don’t worry, I already hate myself for that, but at the time I needed the escapism) it’s that outsiders can’t understand that privileged, insulated world and its weird stressors. Someone familiar with that world can make an impact and be understood by those within it. For the rest of us, it’s too foreign. In this case, the predator worked hard to ingratiate himself with the girls and their families, gaining trust and assuring them he understood.

Gary had sympathetic, youthful qualities that allowed him to win over the girls he worked with, something Piper describes in part as “that gabby female quality that suggests he bonds through mutual disdain.” I had to smile at that, it almost seemed like he had a Rorschach-esque ability to show each girl what she wanted or needed to see. Weiss herself tells a compelling anecdote of what first attracted her to Gary – en route to a tennis match, she noticed some girls commuting separately in a car instead of on the bus, where she felt trapped and anxious. She asked her mother to hire him as a coach.

The book starts out strong, and establishes an underlying anxious darkness, similar to Curtis Sittenfeld’s novel Prepto which this has been compared. There’s something inherently menacing in adolescence and the teenage experience, whether it’s lived amidst the cushy comforts of the Upper East Side and the urban high class or somewhere leaner and grungier, and all the in-betweens of suburbia. The bullying, the cliques, the struggle to fit in, the angst, anxiety, family fights, the general stress of having your eyes opened to more of the world and its evils is a scary atmosphere regardless of how and where you experience it.

I liked that aspect of the storytelling and Weiss is adept at conveying it. Actually she does it so well that I even felt anxious at times, remembering parallels in my own life or maybe just being able to empathize with some of her problems. “Some” being key. The element of privilege and wealth is a strong one, plus stories of teenage parties and boys didn’t add much, I felt. Maybe I would’ve enjoyed this book more when I was younger. Now it feels like well-trodden ground without adding anything fresh.

I hesitate to call this true crime, because while there’s a crime, or several, this is much more Piper’s story. The crime element isn’t much more than what’s Google-able about Wilensky. It’s all filtered through her lens and involvement, even peripherally. And what it means to her is everything to do with her life at that time. It feels like a story she’s needed to tell for a long time – she reveals herself to be as peculiarly obsessive as Gary was, fixating on him and the past. He was obsessed with teenagers, and she became obsessed with him. “Obsession, that’s what this was all about,” one investigator tells her, reflecting on Wilensky’s case. The whole book is about obsession, its dark and disturbing aspects but also the surplus of pain that creates it and where that pain came from.

Most disturbing, and unpleasant to read, is that part of Piper’s fixation is that she was never the favorite. Gary offers an additional free weekly lesson, telling her mother it’s because she’s promisingly good. And although he confides some adult things to her, he doesn’t groom her as extensively as he does the unnamed girl he’d selected to kidnap. She admits knowing this feeling is wrong, yet it crops up often and adds to the current of uneasiness running throughout.

She handles the case sensitively, exploring any avenue open to her, although most potentially revealing sources refuse interviews, so this becomes mainly her teenage memoir and less a crime story. The writing is uneven, but sometimes there are dreamy considerations that gave me pause, like “Is there a word for a fantasy you don’t enjoy, a waking dream that you didn’t have, but rather it had you?”

Elsewhere, her failed relationships, her mother’s criticisms, teenage cutting, and life directions or ruminations that weren’t fleshed out enough to be meaningful here, making them uncomfortable or incomplete in the context, were less compelling.

Speaking to investigators involved with the case now, Weiss says what she would’ve told police back then, if they’d interviewed her. “I would have defended his character. That’s kind of what I’m interested in most. Why I was so protective of Gary, why I felt so connected to him, even after his horrific crimes were committed.”

The investigator tells her that’s a typical MO for this type of abuser and predator of young women. The psychology is complicated. She doesn’t offer clear reasoning for her own feelings, but it’s accurate – the whole situation is muddled and complex, feelings overriding fact and reason. Like any obsession.

Weiss’ research and inclusion of personal records are what pulls the story through, making it strange and fascinating, digging through official archives and newspapers as well as her own and and her mother’s collections from the time. A readable if uneven and sometimes uncomfortable look at obsession and the growing pains that afflict some people for life.
Verdict: 2.5/5

You All Grow Up and Leave Me: A Memoir of Teenage Obsession
by Piper Weiss

published April 10, 2018 by Harper

I received an advance copy courtesy of the publisher for unbiased review.

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