Editor's Note: Rob Sheffield is a contributing editor at Rolling Stone, where he writes about music, TV, and popular culture. He is the author of Turn Around Bright Eyes and the national bestsellers Love Is a Mix Tape and Talking to Girls About Duran Duran. For Biographile's That Summer series, in which authors share personal stories on the summers that shaped them or their subjects, Rob remembers a summer of firsts.

Summers are an excellent time for firsts, because so many of these firsts turn out to be lasts. Something about the footloose sticky-but-slippery heat of summer goes with the courage to try things, even if you suspect you won’t have the emotional stamina to keep them going. My twentieth summer was full of firsts, many of which might seem spectacularly long-delayed to anyone but a bookish little nincompoop like my twenty-year-old self. (And if you read the last sentence and said, “Actually, if you were twenty, this would have been your twenty-first summer” -- congratulations! You probably are my twenty-year-old self.)

I worked all summer at my college library, shelving books back in the days when college libraries had a mandatory-smoking policy -- the study tables had little tinfoil ashtrays on them. After shelving the HQs and PRs and MLs, my Walkman full of Husker Du or The Smiths or Whitney Houston or Madonna, I would sit under a tree perusing St. Augustine’s Confessions with my daily bread: two WaWa dogs smothered in cheese sauce and a fountain soda the size of a small child. I spent my nights in a house full of hippie housemates strumming their guitars, packing the bong, and watching TV with the sound down while playing Laurie Anderson’s "Big Science" looking for cosmic Synchronicity. I’d recently had my first beer (not bad), and my first kiss was still a summer or two down the road, but I made a project out of other grown-up firsts I’d normally be way too chicken (or lazy) (or shy) to try. It was my first lease, for one thing -- $120 rent for the summer, sleeping on my futon in the corner of a back room.

My first cup of coffee was the beginning of a lifelong romance. My first self-haircut was a disastrous experiment -- after seeing a Replacements all-ages show, and being impressed by how Paul Westerberg was able to sing “Hold My Life” while huffing and puffing the bangs out of his eyes, I decided to cut my own bangs, which merely made the barber laugh at me when I fled to her for solace a couple of hours later. When she asked, “Did you cut this yourself, kid?” I briefly considered lying, then thought of St. Augustine and confessed. My first puff of marijuana. My first puff of hash. My first realization that it wasn't hash at all -- just the fruit of my banjo-plucking roommate paying a twenty in Washington Square Park for a baggie full of Play-Doh.

But the most fun of those firsts was playing a song on guitar for the first time, with generous coaching from my housemates. I mastered three chords -- E, A and C, I think? Or was it D? -- and began a twenty-minute version of “Louie, Louie,” which I stretched into a medley with “Love Stinks” and “More Than A Feeling.” Each chord change meant studying my fingers and starting from scratch, so I took the tempo slow, and sang along as soulfully as I could, stretching out the vowels until they ached. Looouuu. Eeeeee. Loooouuu. Eyyyye. I pressed record on my trusty boombox, knowing I had to catch this moment on tape because I would never again be fluent enough on guitar to strum a song all the way through. I was right. It was a first that proved to be a last. But I still have that tape, and when I put it on and listen to the clumsy strum of my twenty-year-old self, I’m grateful he gave this first a try.