The twenty best viral personal essays of the past 20 years
Sites like xoJane and Jezebel once churned out a steady stream of confessional writing, most of it by women.
I recently scrolled upon a tweet that really spoke to me.
"I think it's exciting that nymag/the cut is going all in on the xojane ‘public self-flagellation via humiliating personal essay' model,” wrote @focusfronting.
I've written before about this strain of early/mid-aughts writing that seemed to disappear as the decade wrapped up. For 10 years or so, sites like xoJane and Jezebel — as well as first-person verticals at other, larger publications — churned out a steady stream of inadvisable tell-all essays, most of them by women.
At their best, these "squirmy, awful, brilliant pieces” encouraged readers to "be a lot more honest about the human experience,” per one former xoJane editor. At their worst, these harrowing or tone-deaf or self-sabotaging confessions left you feeling like you'd read an (unwell) stranger's journal.
Wherever they fell on this rickety spectrum, by 2017 they had mostly died out. The fickle economics of online publishing had shifted, and the cultural mood had turned against the "first-person industrial complex.” Today, I'm delighted — like, sincerely delighted — to bring you some excerpts from that glorious canon. I had so much fun compiling this that capping it at 20 was kind of a challenge.
My criteria for this first guide were subjective, so please write and tell me what I missed. But generally, I looked for first-person essays that demonstrated a degree of "radical transparency” and earned widespread notoriety when they published. Some of these essays are unsettling. Many will make you question the author's health/judgment. But each is a perfect capsule of internet history — and I love all of them for that.
Please note that links to archived websites — namely, xoJane — will NOT work on your phone. You'll need to boot up a laptop or desktop for those ones.
The Links Guide to (In)famous Internet Essays
"Ten Days in the Life of a Tampon,” by Moe Tkacik for Jezebel (May 2008). This iconic account of a wayward tampon and its eventual retrieval set the tone for every essay to come after. In hindsight, I don't think Tkacik — now a senior fellow (!) at an economic think tank (!!) — got enough credit for her self-awareness. "WARNING: The following is a really, really gross story,” she begins. "It may even qualify as "beyond gross." It also: signifies nothing, gives you wayyyy too much information, and is told by a total idiot.”
"It Happened to Me: There Are No Black People in My Yoga Classes and I'm Suddenly Feeling Uncomfortable with It,” by Jen Polachek for xoJane (January 2014). Whatever happened to Jen Polachek, the well-meaning white lady whose tone-deaf yoga-class "revelations” sparked a torrent of outrage a decade ago? I couldn't tell you — she scrubbed her online presence (and maybe changed her name??) after posting an apology on Medium.
"On Falling In and Out of Love With My Dad,” by Natasha Rose Chenier for Jezebel (February 2015). Rather like 10-day tampon, this piece needs no introduction. Jia Tolentino also interviewed its author.
"I Spent Two Weeks in a Mental Institution, But Left with Better Hair,” by Cat Marnell for xoJane (May 2011). I struggled mightily to pick one entry from Marnell's vast oeuvre, in which she wrote openly and often about her drug use, sex life and general dysfunction. This one won out because it beautifully packs a whole narrative arc into 300 words. It's like the "for sale: baby shoes” of millennials.
"This Is What Happened When I Drove My Mercedes to Pick Up Food Stamps,” by Darlena Cunha for The Washington Post (July 2014). This essay — on the humiliation of getting judged at the WIC office, and more broadly about the process of losing money and privilege — ranked among the Post's most-read stories that year and earned the author an appearance on CNN. Personally, this one does not offend me. A kinder editor might have cut some lines out. Cunha and her family are, fwiw, apparently doing much better now.
"It Happened to Me: My Gynecologist Found a Ball of Cat Hair in My Vagina,” by Michelle Barrow for xoJane (September 2015). A classic; 10/10; speaks for itself.
"I Believe in Love,” by Emily Gould for Gawker (July 2007). In a fascinating, longform 2008 essay about the hazards and highs of online self-disclosure, Gould referred to this widely viewed post as "one of the worst things I've ever written.” Please read the essay, too — it's really good! And then consider the fact that Gould is still writing viral, tell-all relationship essays, 16 years later.
"It Happened to Me: I'm Living Like I'm in The Victorian Era — from Corsets to Washing Bowls to Writing in Liquid Ink” and "I Love the Victorian Era. So I Decided to Live in It,” by Sarah A. Chrisman for xoJane and Vox, respectively (November 2013 and September 2015). Come for the headlines and stay for the photos, as thousands of readers did years ago: Chrisman and her husband, dressed in hand-sewn garb, light oil lamps and ride old-fashioned, big-wheel bicycles. I'm delighted to report that, to this day, Chrisman maintains a very active YouTube channel.
"My Former Friend's Death Was a Blessing,” by Amanda Lauren for xoJane (May 2016). This piece lasted barely 24 hours before xoJane editors took it down, realizing — too late! — that celebrating the death of a person with mental illness was low even by their low standards.
"I'm Not Going To Pretend That I'm Poor To Be Accepted By You,” by Rachael Sacks for Thought Catalog (October 2013). Thought Catalog, in its heyday, had two essential modes: shameless trolling and earnestness verging on fervor. To this day, I'm not sure where this one falls, but lines like "I am sorry that I was born into great financial circumstances” seem to nudge it into the trolling camp. Incidentally, I will not be linking to any of TC's *most* infamous/viral takes, all by Proud Boys founder Gavin McInnes.
"The Day I Put $50,000 in a Shoe Box and Handed It to a Stranger,” by Charlotte Cowles for The Cut (February 2024). I still think it's very brave that Cowles — a grown woman with no need to "break into the industry” or "get her name out” — admitted to an audience of roughly two jillion people that she lost her life savings in a shoe box.
"My Boyfriend, a Writer, Broke Up With Me Because I'm a Writer,” by Isabel Kaplan for The Guardian (December 2022). Kaplan penned this polarizing essay after the publication of her debut novel, which allegedly caused her jealous writer boyfriend to dump her. Said novel is now listed on Amazon with the title "Not Safe For Work: Author of the viral essay 'My boyfriend, a writer, broke up with me because I am a writer'” … so I'm guessing this all worked out for her.
"If You Have Savings In Your 20s, You're Doing Something Wrong,” by Lauren Martin for Elite Daily (September 2015). Finance blogs and columnists lost their MINDS over this piece, which includes memorable tidbits like "when you live your life by numbers, you strip yourself of poetry.”
"I Am Adam Lanza's Mother,” by Liza Long for The Blue Review (February 2012). Immediate spoiler: Liza Long is not Adam Lanza's mother. But she is the mom of a child with bipolar disorder, who — as part of an argument for better mental healthcare — she compared at great length to the Sandy Hook shooter. All's well that ends well: The essay caught the eye of a research assistant who helped Long's (actual) son get proper treatment.
"The Case for Marrying an Older Man,” by Grazie Sophie Christie for The Cut (March 2024). Comically dreadful, in terms of both craft and content … but still a delicious reading experience.
Caitlin Dewey is a reporter and essayist based in Buffalo, N.Y. She was the first digital culture critic at the Washington Post and has hired fake boyfriends, mucked out cow barns and braved online mobs in pursuit of stories for outlets including The New York Times, The Atlantic, The Guardian, The Cut, Elle, Slate and Cosmopolitan.