The Hard Won Lessons of Lesley Arfin’s Dear Diary 15 Years Later

As a teenager, walking into American Apparel somehow always felt like an act of transgression. Never mind the sleazy ads and bandeau bras—the brand was selling forbidden fruit to the uninitiated, and at the now-shuttered American Apparel on Melrose Avenue, in 2007, two items for sale forever shook my world: a Hitachi Magic Wand™ (the “Cadillac of vibrators”) and a book with a defeated young woman nursing a nose bleed on the cover. At 13, I bought the latter, recognizing something in the young woman’s eyes, the contradictions between her blood and Barbie pink bubble-letter font hovering above her forehead that read, “Dear Diary.”

I remember reading Lesley Arfin’s Dear Diary in one sitting. It probably sat on my nightstand for the year after as evidence of my adolescent awakening. More than 15 years later, the book has developed a kind of terroir, that sweet-and-sour taste that comes with age, like rewatching a movie and coming to identify more with the parents than the kids.

Dear Diary is a collection of Arfin’s diary entries from 12 to 25 years old. At 28, she published her millennial Go Ask Alice (but non-fictional and without the moralizing), a punchy and damning record of a triumphant journey through the varying crises of a Long Island upbringing, heroin addiction, and the heyday of indie sleaze. “It’s about how amazingly shitty it is to be a teenage girl and how much you hate it when you’re there and how much your heart swells when you look back on it as a grown-up,” Arfin writes in the intro.

Based on her Vice column, the twist comes after each entry, where she updates the reader on what’s since happened, or what really happened. She tracks down old crushes, frenemies, and exes (many of whom she hadn’t been in touch with for years) to dizzying Rashomon effect told over AIM. Some follow-ups function as apologia or postmortems; others editorialize decades of heartbreak and angst, Firsts and Lasts, privilege and trauma. “I hate my life. I hate myself. I hate having to repeat the same thing every day,” she writes in December 1993, at age 14.

After, she tells us what she really means: “‘I hate my life’ is teen speak for ‘Things are going pretty good.’” The revisionist history feels like picking at scabbed-over wounds for some relief or conclusion that never comes. It’s in Arfin’s admissions of teenage martyrdom, learning she was both the victim and the villain in a story while she lied to everyone including herself at the time, that we’re reminded time and again how our own private thoughts are often the most fallible and unfair.

Arfin’s epistolary memoir isn’t so much a ghost chase as it is a purse-sized time machine. Its campy book design mimics an ersatz teen diary, padlocked-shut with a magnetic side flap and color-coded in pink blush and fuchsia. Inside, Arfin and all her former selves clash, where a baby picture smiles next to her hitting the bong; a handy “Experience Timeline” charts every phase, drug, and sex act; expressive and highly stylized illustrations color in the rest, like shaving her legs or shooting up in front of her cat.

Model-actress Chloe Sevigny writes in the foreword that she found an uncanny comfort in Arfin’s confessional prose, where “both of us were bored outcasts from the suburbs of New York, and both of us narrowly escaped getting lost in the wrong crowd during our ‘bad girl’ phase.” Even for someone who didn’t grow up in an upper-middle-class East Coast family, I also found myself reading words that seemed to have spilled from my own mouth. Dear Diary spoke to the universal in its specificity and treated a teen’s voice as seriously as literature.

Her long-running thesis throughout the book concerns the diary’s purpose. “Ever notice happy kids don’t write in their diaries very much? They don’t have to. Life’s too fun,” she writes. “Diaries are for when life isn’t fun. They’re for figuring what went wrong.”

Arfin doesn’t use her diary so much anymore. There’s no burning emotion fueling a diaristic rant about how badly she wants to be a good mom, she told me over Zoom last month. “It’s not the same kind of obsession that I had with love and romance, which drugs are included in that. On one hand, all the romance was an addiction, and on the other hand, all the addiction was a romance.”

Today, Arfin’s a successful TV writer living in Los Angeles. She never wrote another book but credits her debut with catching Lena Dunham’s attention, leading to a staff gig on the first seasons of HBO’s Girls, springing into another Judd Apatow collab with Netflix’s Love, co-written by and starring her husband Paul Rust, with whom she has a five-year-old daughter.

“The biggest transformation that threads throughout Dear Diary is going from preteen into young adulthood,” she says. “But since then, my transformations have been much closer together and more condensed, with many more of them. Because I can handle it. I’m an adult, and I can drive myself to the movies. I don’t need to wait for a ride from my mom and then like, cry about it or whatever. There’s a lot more control that comes with adulthood.”

Arfin has lived many lives since she published Dear Diary 15 years ago. “For starters, I think I’m a much better writer,” she says, acknowledging the dated references and language informed by early Vice Magazine-ese. The first person thanked in the acknowledgements is Gavin McInnes, Proud Boys founder and Vice co-founder, and later there are pejoratives that we’ve since ousted from the lexicon, like the R-word or calling something “gay” as an insult. I remembered how much culture back then was couched in snark and how “irony” was wielded as a shield against accusations of either genuine harm or genuineness, period. (Edgelords, I guess you would call them, were mainstream.) I wondered how today’s chronically online will fare, for better or worse, 15 years from now.

“I regret a lot of that because it’s alienating, and also that kind of joke doesn’t hold up,” she says, adding she would have been braver with some of the phone calls she had to make for her updates. “I think I would be kinder with some of them, rather than try to be as funny and scathing as I could be because it was Vice, and I wanted everything to be coded in that tone.”

So much of what fuels Dear Diary, and young adulthood, is the excitement and its attendant whiplash. These days, what excites Arfin, now 43, isn’t marriage or work or motherhood. I bring up the TV show du jour, Fleishman Is In Trouble, swirling around those same themes, but she hasn’t watched it yet. “I disagree with the idea that when you become a mother, you lose your identity,” she says. “That’s fucking bullshit. Then you didn’t have an identity to begin with.”

What fulfills her, instead, she says, is making (or fixing) things. She’s a serial hobbyist and deeply devoted to crafting—she even has a podcast about it, called Filling The Void, where she talks sculptures with Kristen Bell or sewing and dancing with Margaret Cho. “I love the hunt,” she says. “And I guess metaphorically, that’s true as well.” Soothing hobbies keep her hands busy, but it’s also about procrastination and still feeling productive even when she’s not writing.

Arfin is still an open book, so to speak. She asks me my age because I think she knows some of my questions are more personal than professional. When I say 29, she jumps at the chance to talk about the “very real” Saturn Return, when her 30s brought a slew of new experiences, good and bad, all exhilarating and fun until they weren’t. And I wonder if that’s when growing up happens: when you can find out how to satisfy yourself without outside approval or honorary degrees, and you settle into the stillness and just buy the glue gun already.

Beyond posterity or self-absorption, Dear Diary was always about subverting the writer’s illusory ideal. “In the back of my head there was always the fantasy of having my diary published,” she writes in the afterword of her book and commits to paper what every one of us has thought at one point.

I’m not sure if Dear Diary is ready for a generation of readers, yet. It’s probably best revisited by those who first bought it, who can identify with what they once saw in themselves. We end the interview when her daughter comes home, and Arfin doesn’t have much time to pick over the past anymore.