Thirteen Things a Middle-Aged Man Can Learn From the Baby-Sitters Club

How Kristy, Mary Anne, Claudia, and even Stacey taught this Dad to live his best life.

Jack Shepherd
15 min readDec 29, 2021

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All photos: The Baby-Sitters Club series

I’m the host of the Baby-Sitters Club Club podcast (now called Strange Bedfellows). This essay is reprinted from the excellent collection We Are the Baby-Sitters Club: Essays and Artwork from Grown-Up Readers.

I’m a Mary Anne. I like to read and I’m shy. Wait, no, that’s not quite right. I’m a Kristy, because I am a control freak; a big-but-not-entirely-thought-out-ideas guy; an optimist. I think, with all deference to your extremely interesting approach to this particular problem, that you should do it my way. Actually, I’m a Mallory. Confident. Practical. Would probably be much better off in a boarding school for the terminally earnest somewhere in rural Massachusetts. OK, no. I am none of these things. Or all of them? Hard to say, but what I definitely am is a forty-one-year-old man who has read every single BSC book, every Mystery, every Super Special, all of the California Diaries, and somewhere north of seventy Little Sister books. Today, as it happens, I am embarking on the first installment of the Friends Forever series: Everything Changes. I hope, very much, that everything doesn’t change.

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Jack Shepherd

I have a newsletter about crossword puzzles and a podcast about rom-coms. Formerly editorial director @BuzzFeed. Email: JackAShepherd at gmail