Twenty years ago this month, Google launched Gmail. At first, user numbers were deliberately kept low, and those with access would hoard invitations and bestow them on friends like precious gifts. Once you were on the inside, though, a whole new world opened up. It’s difficult to remember now (if you’re old enough to remember), but we used to delete our emails. The big-name providers — AOL, Hotmail, Yahoo! — were so stingy with storage that users had to regularly scrub their inboxes, tossing messages into a digital burn box like diplomats abandoning an embassy. Google, however, gave everyone a full gigabyte of storage, enough in those lower-res days to keep, well, everything.

Because of that decision made in Mountain View, we now have a huge accidental archive of our collective past. Awkward flirtations, drunken rants, earnest pleas; friendships fraying or rekindled, personae tried on and discarded, good jokes and bad decisions; every dumb or brilliant or anguished thing we wrote below the subject line — we have an instantly searchable record of it all. To mark the anniversary of this revolution, the editors of New York asked some of our favorite writers to excavate their individual archives and tell us — with dismay or pride or chagrin — what they saw.

The author of several novels, including, most recently, The Bee Sting

Gmail first appeared the year I turned 30. Around me, people I knew were doing hitherto unthinkable things like buying houses and settling down; later that spring, my friend Jonathan, whom I’d known since I was 8, was getting married.

The writing was on the wall: After years of evasion, we were being dragged into adulthood. My new Gmail account was a not-insignificant part of that journey. Until then, I’d had a charmingly whimsical Hotmail address — great for staying in touch with girls I’d met while Interrailing, but not ideal for communicating with prospective employers, editors, etc. Would you trust your database management to mysticaldreamer3125? Or look forward to running into stonedsoulwarrior every day at the watercooler? I saw the Gmail account, which — also hitherto unthinkable — incorporated my actual name, as marking my transition from scruffy, lovable crypto-hippie into ruthless, sharklike grown-up.

Pretty much every other email I wrote at that point related to my approaching 30th birthday. My sent folder is filled with lamentation over the passing of the years.

“I really do feel awash with feelings of mortality, meaninglessness, having wasted my life/not wasted it enough, all that. Positive attitude, though: I did think that I would be totally bald by now.”

At that point, I was living in a shared house while writing my second novel. That had seemed a fine way to pass my 20s, but now I was beginning to wonder if I’d made a serious wrong turn. Everyone I knew was getting real jobs and taking out mortgages, trying to get onto the property ladder. It felt like my whole generation was undergoing a metamorphosis, like a corporate butterfly emerging from a chrysalis made of Slint T-shirts. I, meanwhile, was living the same way I had since I was a college student. Only now I was old!

My friend Loren — then still comfortably in her mid-20s — enjoyed all this existential hand-wringing. On my birthday, she sent me an email headed YOU ARE YOUNGER THAN ADRIEN BRODY! BUT OLDER THAN BUFFY, with an mp3 of LCD Soundsystem’s “Losing My Edge” attached. I wrote back to her the next day with a hangover and my initial impressions of the Other Side: “The first lesson of your thirties is that you can no longer party as if you were twenty-nine.”

Jonathan had chosen me and our mutual buddy Justin as his groomsmen; any doubts he had about his upcoming wedding related exclusively to us. “Fellas, I will need you to wear suits on the day,” he wrote. “I have taken the liberty of picking these out and paying for them. I now need you to go to the shop to be measured. I think the simplest thing is for me to drive you to the shop myself. It’s not that I don’t trust you, it’s just that the shop is hard to find and there’s a time element now.” (The phrase “It’s not that I don’t trust you” appears numerous times in his emails.)

The wedding was a huge success. “Lots of friends, everybody together, beautiful venue, Justin and I immaculately tailored,” I wrote to Loren. There had been romance, too. “Late into the night our schoolfriend Noel got in a heated argument with a girl about whether Cardinal Ratzinger would make a good pope [John Paul II had died a couple of weeks before]. Somehow this ended up in her sleeping with him (Noel, that is, not Cardinal Ratzinger.)”

At the wedding dinner, Jonathan closed his speech by telling his new wife, “Being with you makes me look forward to the future.” That line made a big impact on me; until then, I don’t know that looking forward to the future had ever occurred to me as something you could do. Suddenly, middle age — as I then saw it — didn’t seem so bad.

The midlife crisis enjoyed a further uptick a few weeks later: “I finished my (preliminary) (illegible) first draft on Friday. 1090 pages of unprintable chaos! Actually got a warm glow and since then have had a renewed sense of connection to and love for the world … I feel like an animal coming out of hibernation.”

Another five years would pass before the book saw the light of day. Still, for the first time, I could look at the future and just about see myself in it — which was good news because, as my 30-year-old self would learn, the future just keeps on coming.

Looking back, I find it hard to relate to the issues I thought I had in the Gmail era. Confusion and doubt seem a small price to pay for all that freedom. But of course I’d think that; everyone thinks his problems are the only real ones. For all of his complaining, I’m glad my 30-year-old self kept going with his book; I’m sure he’d be glad to know that I’m still keeping going 20 years later. Also that — though I can hardly believe it myself — I’m still younger than Adrien Brody.

Author of six books, including the memoir Grief Is for People, which was published in February

In 2014, a group of hackers calling themselves Guardians of Peace leaked thousands of emails from Sony Pictures employees, sending a collective shudder up the spines of those of us who’d spent the previous decade using our work accounts for “us” talks and medical missives. “I still love you. Signed, Sloane Crosley, Associate Director of Publicity.” “I think the ointment is making it worse? Signed, Sloane Crosley, Associate Director of Publicity.” My entire 20s passed through that Random House account, an Ellis Island of digital mistakes. I did not succumb to Gmail until I left corporate America in 2011, at which point I sent my new self a handful of exchanges from my old self. Which means I did my survey of the early aughts long ago. But so unwisely. Imagine Harrison Ford in Indiana Jones and the Last Crusade, but instead of picking the Holy Grail, he picks a list of midwestern media contacts, all of which will bounce back within two years.

I have but one substantive exchange from that time, and I can’t imagine why I held on to it. Or why I forwarded it to myself to begin with. Perhaps I envisioned a scenario in which I’d one day have to blackmail myself. It spans the course of a few days in 2004 and contains the most wince-inducing nonsense between me and a male reporter, mostly my doing. I am trying to prove my intelligence and disaffection so he will cover the books I will eventually recommend to him. After he doesn’t come to a party, I write, “You missed it. Might vs. Lingua Franca keg stands, whoever chugs with more irony gets put back in print. I left around 10:30 with a friend and we painted the town puce. Went to some establishment called PM which is an on-the-nose name for an on-the-nose place. Home by 2:30AM!” As the exchange goes on, I throw different versions of myself at the wall to see what sticks. I assumed my 2:30 a.m. was his 9 p.m. But I was wrong: “2:30. Yeah, you’re 25.”

Maybe I sent myself the exchange because this was before I understood how banter could mimic something else, particularly among people who traffic in references both for a living and as a means of flirtation. It should surprise absolutely no one that eventually the reporter and I went on a date that I did not fully realize was a date. Things ended amicably with a bit of harmless annoyance on everyone’s part. Or maybe I kept it because, in the last segment of........

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