Sad-Maxxing

In her 2018 memoir You All Grow Up and Leave Me, the journalist Piper Weiss recalls her teenage years as a tennis player under the guidance of Gary Wilensky, who ran his own coaching company, Gary’s Girls and Guys Adult and Junior Tennis Programs, in New York City during the 1990s. Wilensky was not a professional tennis player, and he wasn’t even that talented on the court. What he did have, as Weiss explains, was “a natural ability to read people, easily detecting their strengths and weaknesses.” He also made tennis fun. Other coaches might bully or belittle young players, but Wilensky presented himself as “an entertainer, a clown with a sack full of gags, doling out carnival prizes on the courts, and showing up for lessons in the occasional costume.” At some point the Eastern Tennis Association named him coach of the year.Like Weiss, I took lessons through Gary’s Girls and Guys, for several months starting when I was eight years old. Wilensky was never my teacher, but he was always around—a rumpled figure with an air of passive benevolence. He was also head coach for the tennis team at my all-girls private school, and I would often see him in the lobby, decked out in a polyester ...