DAN ZEVIN, outfitted in khaki shorts and a faded blue T-shirt from Greek Corner restaurant, is situated comfortably on a squat, beat-up couch at the Someday Cafˇ, in Somerville. A mass of Andy Dick–like unruly curls falls down around his head; his eyes are surrounded by smile crinkles. Between bites of a bagel and sips of strong coffee out of a pint glass, the local humorist is reflecting on the best ways to cash in on unwanted wedding loot. Abruptly, Zevin interrupts himself and thrusts out his left hand, showing off a gold wedding band. "Now that was hard," he says with a raised eyebrow, a grin creeping across his face.

"Sometimes I look at it and I’m like, ‘Whoa, what’s that round object doing on my finger?’ It’s kind of cool though — do you like it?" Encouraged by a nod and a smile, he continues, in a singsong voice, "Downtown Cross-ing." His face lights up with a proud smile. "I think it was like ninety-nine bucks. That was a trip, shopping for a wedding ring. There were all of these jewelers in Downtown Crossing, one after another. It’s not unlike shopping for a car or an air conditioner. You see the same exact stuff everywhere, except at one place it’s going to cost $10,000 and at another place it’s going to cost a dollar fifty."

Ba-dum-bum. And there you have it: Dan Zevin paring down yet another important life transition to an arch one-liner. Dubbed the Dave Barry of Gen X — or, better yet, a straight David Sedaris — Zevin, author of three books and a regular contributor to Details, Rolling Stone, and Maxim, got those smile lines by reducing life’s formative events to comic ash.

The 37-year-old Cantabrigian first ushered his peers through the rites of passage coming their way in Entry-Level Life: A Complete Guide to Masquerading As a Member of the Real World (Bantam, 1994), which explained to recent college grads how to fake a rˇsumˇ, deal with bogus roommates, and get through nine-to-five days spent in an office cube. Zevin hands over a copy of the book, now out of print, with laughs and apologies. A long, sprawling coffee stain marks the book’s top-left corner. It’s classic Zevin: casual, a bit rumpled, clocking a mental age of around 25. "That probably happened here," he says, looking around the Someday Cafˇ.

Next, after navigating the ring hawkers at Downtown Crossing, negotiating the A-list, and managing all the other stress involved in wedding-day planning, he published Nearly-Wed Handbook: How to Survive the Best Day of Your Life (Avon, 1998). And today, Zevin is musing about another phase of life: getting old. In fact, after finishing his coffee and talking about his new book, he has a very adult doctor’s appointment with his dog, Chloe. "We have the same injury," he explains. "We both tore our ACLs."

Zevin’s aches, pains, and new sources of embarrassment are detailed in his latest book, The Day I Turned Uncool: Confessions of a Reluctant Grown-Up (Villard), an account of the various ways Zevin found himself transitioning from Bud to Burgundy, from video games to golf, from Self-Employed Slob to Employer of a Cleaning Lady.

With humorous echoes of P.J. O’Rourke and the writerly agility of Dave Eggers, Zevin shines at speaking to the young(ish) masses, universalizing his personal life-changing experiences, and ultimately leading the fast-sobering, fast-aging Gen X masses to snickers of self-revelation. Consider the latest — an ode to all things "uncool," a sort of jokey gasp of submission for the slacker set. "I’m sort of looking at it now like I’m taking back the word uncool," Zevin says. "Like how the gay community has taken back the word queer or like the African-American community has taken back the word nigger. For me it’s like, uncool. It’s all about solidarity now, and uncool is cool." He pauses. "So I’m cool with it."

ZEVIN is comfortably situated in Boston these days, and as he tools around town in his smelly old Jeep, it’s hard to believe he hasn’t always lived here. But he was raised in Short Hills, New Jersey, outside of New York. Save for a fellow named Andy Schwartz, Zevin says he was the only Jew in his high school. "Now, the town is like a shtetl."

He showed an early interest in journalism, poring over each issue of Rolling Stone as a teenager. "I was absolutely addicted," he says. He eventually went on to study journalism at New York University. At the time, Zevin says, he was a sort of country-club bumpkin. "It was the ’80s, the punk thing was happening, everybody around me had, like, safety pins in their face," he recalls bemusedly, "I arrived in my little Lacoste shirt with the collar up."

While at NYU, Zevin took an internship at Rolling Stone — despite warnings from the mag’s editors to run the other way. "When I was interviewed, the first guy who interviewed me looked at me and said, ‘I have to tell you, this is a really shitty internship. It’s awful. You’re going to do nothing; you’re going to staple.’ " Three other editors also advised Zevin to walk out the door. But he opted to stay. "I said, ‘No problem. I’ll do anything. Heavy lifting? Whatever.’ I just wanted to be there. I thought I was going to hang out with [publisher] Jann Wenner and have lunch with him. I never formally met him. We rode the elevator a few times, but I was so nervous I could barely speak."

Zevin did in fact perfect his hole-punching skills at Rolling Stone. "I did staple. I did a lot of hole punching and I did a lot of Xerox-machine work. And sometimes I didn’t even show up. No one even missed you if you were gone. But later, when I started to pitch them article ideas, when I got out of school and started writing, I just would say, ‘I interned there, you must remember me. I was the intern who did all your hole punching.’ " He pauses. "And that went a really long way. They just liked that I was part of the family."

After graduating in 1986 — "Aren’t I old?" — he came to Boston, mostly to join his girlfriend Megan Tingley, now a children’s-book editor at Little, Brown. Zevin took a three-month sublet to test out life up north. Apparently, it passed. "Here it is now, 16 years later," he marvels. "The girlfriend is my wife! Yes. It worked out beautifully."

Oddly enough, Zevin soon found himself working as the "gear" editor for now-defunct Walking magazine. His tasks included tearing apart shoes and inspecting insoles, writing up stories on walking paraphernalia, and, best of all, reviewing videos of walking. "I’d watch them on fast-forward," he laughs. Meanwhile, like many of his fellow "entry-level" lifers, Zevin made use of his employer’s fax, photocopier, and computer to freelance. Unable to sit through the walking videos without laughing, he wrote up a satirical review for Spy magazine. And while tending to Swiss Army’s latest snug band and sizing up the ˇlan of various strides, Zevin began covering college-related stories for Rolling Stone, cashing in on his former hole-punching entrˇe.

During his five-year tenure at Walking, Zevin also got out his first book. "I’d basically used up my hard drive writing Entry-Level Life," he admits, adding with a devilish smirk, "their hard drive."

And thus began his real career: humorist. Entry-Level Life, a catchy, list-filled pseudo-guide to entering the full-time workplace, was a huge success that made the Boston Globe bestseller list and won rave reviews in the New York Times, the Miami Herald, and a spot on Liane Hansen’s National Public Radio show Weekend Edition, among other venues. How could it miss, with chapters such as "Mad Lib Cover Letters," "Inferior Decorating," and "Climbing the Corporate Stairmaster"?

A few years later, Zevin landed at another of life’s junctures. Having proposed to Tingley, the muse who enticed him to Boston from New York, Zevin found himself wading through a sea of pesky wedding minutiae. "We got sucked into this wedding vortex," he recalls, in a rare moment of seriousness. "I would wake up late at night and be, like, worried about the seating plan. Megan and I were literally having fights over things like: do we really want to register for that specific dip-and-chip bowl? It was the stupidest shit. And that’s always a sign that there’s some comic potential." He chuckles, adding, "When you start taking yourself way too seriously." And thus was born the Nearly-Wed Handbook: How to Survive the Best Day of Your Life, a male parody of the panic-inducing girls’ guides to taking the plunge.