
Things I Probably Shouldn't Share
Confessions from an Unapologetic Oversharer
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Sean McDermott
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Things I Probably Shouldn’t Share: Confessions from an Unapologetic Oversharer is fifty-three true stories that prove the strangest, most ridiculous moments in life are the ones that stick. Usually beginning with: “Okay, I probably shouldn’t tell you this…”
Inside are the kinds of stories you only admit in passing: crying because you never got to be the Monopoly dog (and always ended up the thimble), practicing Wonder Woman spins until a ceramic goose lost its wing, hauling cartons of Winstons out of a concert at age eight, getting fired and replaced by an actual stick, and watching a little girl scream “Piglet, it’s me—Trina!” in a Disney parade meltdown you’ll never forget once you picture it.
With the dry wit of David Sedaris, the heart of Jenny Lawson, and a dash of Augusten Burroughs, Tom Gloude Whittaker turns awkward childhoods, messy families, bad jobs, strange vacations, and everyday disasters into something hilarious, oddly comforting, and—sometimes—surprisingly moving.
These aren’t stories of wisdom. They’re reminders: that the weirdest, most embarrassing memories are often the ones that connect us. And that oversharing, in the right hands, might just be the most human thing of all.
©2025 Tom Gloude Whittaker (P)2025 Tom Gloude Whittaker