(Photo: Christopher Anderson/Magnum Photos/New York Magazine)

A Union Square diner past its trendy prime, Coffee Shop looks like just a convenient place to meet the writer Junot Díaz a few weeks before the publication of his much-anticipated second short-story collection, This Is How You Lose Her. But it turns out to be freighted with a messy swirl of associations for him. This is where, a few years ago, Díaz arranged to meet his personal idol, African-American science-fiction writer Octavia Butler, though their date fell through, and she died before they could reschedule. It’s where, at 26, he signed the contract for his debut collection, Drown, which made him the first Dominican-American literary star. And it also resonates with older New York memories, the kind that “make my art happen”: 15-year-old Díaz, fresh off the express bus from Parlin, New Jersey, for a night of clubbing with his boys, looking longingly through Coffee Shop’s giant windows. “This place had the reputation for all the hot girls,” he says. “You’d walk past and you’d be like, ‘Oh, shit!’ We were kids, man.”

Sinewy and almost too thin, Díaz looks sleek in a tight black collared shirt and Hugo Boss slacks, and flirts easily with our waitress—complaining about how ghetto it is that the kitchen doesn’t have grilled onions. But at 43, and having recently embarked on a new relationship, Díaz seems, more than anything, wistful for those girl-chasing days. “Look at them, they’re like 18,” he says of the waitresses. “I realize, man, when I was first running around New York, somebody probably just wanted to hug me.”

Yunior, which is what friends and family call Díaz, is also the name he’s given to the very Díaz-like lead character in both Drown and This Is How You Lose Her. A Dominican immigrant with an absent father and a fluency in both Spanglish and nerdspeak, he also has some serious issues with what Díaz casually calls “masculinist subjectivities.” The contract Díaz signed here seventeen years ago called for Drown and then a second book, about “the rise and fall of a young cheater.” Its working title, “The Cheater’s Guide to Love,” now belongs to the new book’s propulsive closing piece. Along with two other stories, it employs the second-person present: “You,” Yunior, a writer teaching in Cambridge, destroy a long-term relationship, cycle rapidly through physical transformations (weight gain, weight loss, yoga, back problems), and finally determine to turn all that pain into a manuscript.

“It took forever to get the fucking stories I needed to do this project,” says Díaz, whose lunch conversation runs like an advanced literary seminar taught by a bilingual stand-up comedian working very blue. One early version of the title story began at Rutgers, where he went to college and met his first love; another was set in Boerum Hill, where he lived in a cheap walk-up before Drown was published. Eventually, he put the whole thing aside to write The Brief Wondrous Life of Oscar Wao, a tragicomic picaresque set against the backdrop of his native country’s midcentury Trujillo dictatorship, which won him the Pulitzer Prize. Shortly afterward, he was asked to be on the Pulitzer Prize board, completing his rocket arc into the Establishment.

It was, in some ways, the worst time in his life. Díaz was engaged to marry a lawyer, and, just as Wao was coming out, five years ago, the relationship imploded. “My female friends were fucking pissed,” he says. “That was the one relationship they liked.” He blames it partly on his struggle to finish Wao, and, pressed to choose, he says he’d have preferred a wedding to a Pulitzer. But he knows it’s not that simple. “I wonder if I could’ve just been a better fucking human being and written my book without having to be a pussy about it.” He admits to cheating on about half his girlfriends, but in this case he says he “committed the most unpardonable sin, which is that I made her unhappy.”

That catastrophe—the breakup to end all breakups—became the catalyst for a newer, wiser “Cheater’s Guide.” Díaz was ready, finally, to tackle everything he couldn’t in his scrappier but more tentative first collection: not just his romantic bungles but his brother’s early bout with cancer (which he beat in real life, though not in This Is How You Lose Her). Díaz was well into the book when, about a year ago, he was diagnosed with spinal stenosis. (He had surgery in late June.) A doctor traced it back to years of weight-lifting and a part-time job delivering pool tables during college. It was the perfect injury to give Yunior, amplifying the consequences of the backbreaking working-class, macho culture he could never quite escape.