I was 29 years old and living the dream, or at least my version of it, when everything changed. I was in love with an amazing woman and had a rent-controlled sublet in New York City’s West Village and a good job at a glossy magazine. By any estimation as I now recall my life before it was tossed upside down, my girlfriend and I had no discernible problems.

I was a senior editor at a magazine called P.O.V., which was aimed at young guys who wanted to make a ton of money and spend it trekking in Tibet (tagline: “Work hard, play hard”). Five days a week I walked 10 blocks to my job, hunkered down in my cubicle, shot the shit with the editorial crew, and settled into making life better for twenty- and thirty-something guys who already had it pretty good. And I had it pretty good, too. How hard can things be when your big goal for the day is to write an article for a grooming column on how to get the perfect shave? I was cruising along with my story (“Step 3: Apply a preshave moisturizer to open up pores and loosen hairs”) when Piper called to say four words no one ever wants to hear: “We need to talk.” For emphasis she added, “In person. Right now.”

What had I done? Drunk-dialed an old girlfriend? The ’90s were hazy, but I did not recall that happening. Was her old boss luring her back to San Francisco to produce the follow-up to her smash infomercial for Sweet Simplicity (the ultimate hair remover)? I doubted it.

The 20 minutes until she reached my office from our apartment were long, but I did what I always do: kept going.

I have no memory of the first time I met Piper Kerman. I am told it was in the summer of 1989. I had a job as a counselor at a program called Exploration, or Explo, one part summer camp with all the usual stuff (softball, archery, and, because it was on the rarified campus of Wellesley College, windsurfing) and one part afternoon “courses” taught by college students such as myself. I taught a class in social psychology. I’m not sure what we did for an hour a day for three weeks, save for watching that scary video of the Stanley Milgram experiments (where subjects administered what they thought were real shocks to their peers) and discussing the famous Zimbardo experiment that examines prison guard-prisoner role play. With much more gusto I led a class called “I Got My Tie-Dye at Macy’s: The ’60s Meets the ’80s.” About a dozen precocious teens and I discussed freedom rides and civil rights, read Kerouac and Martin Luther King Jr., and listened to a lot of Dylan.

It was at Explo that I crushed hard on my first lesbian, Susan. I had no idea she was gay because I was a clueless 19-year-old, and she appeared to be keen on another counselor named Leif, a short Nordic-looking guy who everyone fawned over because, well, he was an actor. A Teenage Mutant Ninja Turtle, to be precise. He played Donatello in the movie.

Shortly after I realized Susan wasn’t into guys, she decided that she liked me, and we hooked up. I had no idea then that, for whatever reason, I would love a lot of lesbians in the next two decades, and they, oddly enough, would love me back. This and good hair are the gifts the universe has given me.

Piper had been invited to speak to the students by my friend and fellow counselor, Kristen, as part of a gay and lesbian awareness day program. In 1989, teaching a bunch of 15-year-old summer campers that being gay was OK was pretty damn edgy. I have a vague memory of standing at the back of the cafeteria that had been set up as an auditorium while gays and lesbians talked about being gays and lesbians. But I don’t remember Piper, who was one of the speakers. If I had met this Breck Girl blonde then, I’m sure I would remember it. I was likely staring at Susan, who was surely staring at Piper.

I loved Explo, but I wouldn’t be back. I was graduating college that spring into a job market in deep recession, and I wanted to become a writer, so that summer was better spent learning how to wait tables. Little did I know that at a brewery in Northampton, Massachusetts, Piper Kerman would be doing the same thing.

Piper and I arrived in San Francisco via very different routes, even though we were heading west for the same reasons: to reinvent ourselves. Going to college at the University of Pennsylvania, just 30 minutes from the South Jersey town where I grew up in a loving and occasionally smothering home, had me itchy to expand my worldview. Don, a friend since fourth grade, also had a notion to get out of Dodge after we graduated in 1991. The plan was this: Take as long as our funds would hold out and see as much as the country as possible, with a vague idea that we’d end up in San Francisco.

We camped in our blue L.L. Bean tent. We slept in our car in hotel parking lots and cleaned up in the lobby bathrooms in the morning. In some cities, we called upon parents of friends from college, asking to crash in their guest rooms. We did it because we were 21 years old, had little self-consciousness and lots of entertainment value, and usually ended up being taken out to dinner. In St. Louis, we woke to the smell of just-baked muffins my friend Allison’s mom left us. On the kitchen table was a note that said: “Tom and I will be home at 6 and we’re all going out for burgers. I’ve left you house keys and a map to the city.” We got high and went to the Arch.

We looked for juke joints in the Mississippi Delta. The night we arrived in New Orleans we checked into a youth hostel and then hit the town hard, and shortly thereafter were mugged at knifepoint. Briefly, but with enthusiasm, Don and I looked into renting an apartment in Kansas City and applying for jobs at the weekly newspaper. We encountered a friendly anti-Semite in Texas and were gently propositioned for a threesome by a man who worked at the Carter Center in Atlanta. In Nashville, we snuck into Vanderbilt’s student cafeteria, crashed a frat party, threw up our dinner, and fell asleep on couches in a common area in a dorm. I remember, with absolute clarity, being curled up in the fetal position with a massive hangover the next morning and hearing the voice of what I assumed was an RA saying, “Does anyone know who these two guys are?” and someone replying, “I think they’re Phil’s friends.” We were not.

More than two months and 13,000 miles later, Don and I were in San Francisco. I had long before fallen for the city after a family trip out west and repeated viewings of Vertigo (VHS). After discovering my mom’s beat-up copy of Allen Ginsberg’s Howl among the Mona Simpson and Toni Morrison novels, I started reading Kerouac and the Beats.

My parents have always been a weird bundle of neurosis and contradictions. They never coddled me like Larry Bloom’s parents on Orange Is the New Black, but anyone who knows Carol and Lou Smith can see how they share the Blooms’ overprotective instinct.

My mother was the daughter of a family doctor who took pies as payment when his patients were cash poor; she worked as a high school teacher, then took time off to raise three kids, returning to school to get a master’s degree in social work. My father was the son of a Russian immigrant, Morris Smith, whom everyone called Smitty. Smitty came to America at age four and lived the classic American dream, ultimately owning his own pharmacy in Maple Shade, New Jersey, a small suburb of Philadelphia. My dad is now in his early 70s and still practices law at a small firm he runs in South Jersey, in the same town where he and my mom were high school sweethearts.

But in ways that seem much weirder from my newly acquired perspective as a parent myself, my folks were unconventional. They took my two sisters and me to see Saturday Night Fever in 1977 and covered my seven-year-old sister’s eyes during the nude scenes. We were the youngest people at the Eddie Murphy concert (usher: “You know this show contains very graphic language.” My dad: “Yes”), and for my 13th birthday I took a dozen friends to see Pink Floyd: The Wall.

We were never spoiled, though we were showered with love, with guilt, with expectation. No one was Tiger Mom’d in my family, but my sisters and I caught an intense work ethic by osmosis: It wasn’t until I graduated from high school that I realized most middle-class dads back then didn’t work six days a week.

With the help of grandparents, who embraced every early-bird special they ever met, my parents put three children through college. Their terms and conditions: We were not allowed to apply to school on the West Coast. So perhaps it was both my destiny and suburban-boy rebellion to head west as soon as I was on my own.

In the early ’90s, San Francisco was still years away from its first tech boom, and you could show up with little money and make your way. My six-week search for a place to live ended when I wandered into a garage sale taking place inside a three-bedroom apartment in the Lower Haight. For $800 a month, it was all ours.

I got an internship at SF Weekly, the city’s alternative newspaper, and a series of jobs waiting tables at increasingly worse restaurants, culminating in Pizzeria Uno, where I served $9 lunch specials and drank after my shifts like only a twenty-something with tip money in his pocket can. I started getting freelance writing assignments, which was fortunate, because I was a terrible waiter.

One of my first accepted pieces was for a weekly called East Bay Express. I wrote an overwrought personal essay in response to a Time cover story about Generation X. I don’t have the stomach to re-read those words now, but the piece was illustrated by a guy named Dave Eggers, who had also recently arrived in the Bay Area. Dave said that he liked my story and wanted to get coffee. He had an irresistible charm and a way of making you believe that anything was possible, and he invited me into the crew that would help him launch Might magazine (tagline: “It’s a goddamn brain picnic for the young and restless”). Might was not long for this world, but it catapulted Eggers and many others in its lattice into professional orbits, changing my own life along with it.

Across the country, Piper Kerman was finishing up at Smith College and moving onto, briefly, a similar path. Faced with a terrible economy and little sense of what she wanted to do with her life, she took a job at a brewery in Northampton, where she got entangled with an older woman (known as Nora in Piper’s memoir, and reinvented as Alex Vause on the show). I have to take Piper’s word that Nora, too, had an irresistible charm and way of making everyone in her orbit believe anything was possible, changing Piper’s life along with it. Less than a year later, Piper would tell her lover she was leaving her and the drug world she’d become enmeshed in and head to San Francisco. A few months after settling into the city, Piper was working two waitressing jobs, keeping her secret past very close to her vest, and moving into a flat two blocks from me.

I almost didn’t meet Piper a second time. I stayed in sporadic touch with Kristen from Explo over the years; this was pre-Facebook, when you really had to work to keep up with friends. When Kristen left a message on my answering machine to say that she was in San Francisco, I was pleasantly surprised. She invited me to join her and a friend for brunch, which I almost blew off because I had a writing deadline. But when I realized they were meeting three blocks from my apartment, I powered down my Mac Classic and arrived halfway through their meal at Kate’s Kitchen.

Piper was pretty by anyone’s standards, but blonde, blue-eyed, Waspy girls are catnip for hairy Jewish guys like myself. I zeroed in on her killer calves, the kind you can get only from good genes and miles and miles of running. Piper and I got off to a good start, bonding over our love of Kate’s bacon-cheddar pancakes. The conversation turned to sex. Piper mentioned that her relationship was in a rocky spot.

“What does he do?” I asked.

“She is a law student,” Piper said, without missing a beat and with a bit more irritation than warranted.

Surely, she assumed I was yet another meathead straight guy. Yet my gay cred was impeccable: college thesis on Cole Porter; unpublished op-ed in support of a gay rights march in 1991 in Kennebunkport, Maine; gay roommate.

I rolled my eyes, ate my pancakes, and figured that was the last I’d see of the touchy lesbian. Then the conversation moved on to Melrose Place, the going television concern in 1994. Piper did not own a TV, which was kind of wonderful for someone who had recently transitioned from the food service industry to working for an infomercial company. Piper and Kristen invited themselves over that night to watch it with me and David, my ebullient, red-haired roommate. Piper soon joined David’s gay and lesbian book club and was back in my living room a few weeks later. She was warming to me. She mentioned that she liked my Miller’s Crossing poster and my extensive Tom Waits CD collection, two of the quicker ways to my heart.

Soon enough, Piper and I were both ending relationships—I with a graduate student, she with an aspiring U.S. Olympic softball player. My ex looked like Ali MacGraw, circa Love Story, hers like actress Nancy McKeon, circa her role as Jo on The Facts of Life. We were both intensely driven at a time when few people our age in San Francisco seemed to be. We worked longer hours than most of our friends, who could be found rollerblading in Golden Gate Park by 5:30 p.m. Late-night empathy calls from our offices across town turned into 10 p.m. dinners.

Piper was the ultimate platonic playmate: We drank bourbon, ogled girls, shot pool in lesbian bars, and walked on weekends to all parts of the city, stopping to catch a church gospel service or grabbing a Bloody Mary. Best of all, no one gave me better advice on women, holding nothing back and offering a few pointers. If you’re a straight, single guy, I cannot recommend a no-bullshit lesbian bestie highly enough.

My folks visited often. They loved San Francisco and adored my ex-girlfriend—Harvard grad, tattoo-free, half-Jew that she was—and were taking our breakup hard. As we walked down Haight Street during their first trip to see me after I told them the bad news, we ran into Piper. She was carrying a basket of freshly laundered clothes, her blonde hair bouncing in time to her step—poised, personable, and most likely wearing a sundress. It was easy to see why, as she once told me, she was the friend other friends took along to dinner when their parents came to town.

We said goodbye, and I could see my dad’s brain working as he watched her trot down a street paved with piercings, surly, tattooed video clerks, and pre-Etsy handcraft shops. “Now there’s a nice, all-American girl,” Louis Smith, Esq., announced. “Why don’t you go date her?”

“Thing is, Dad, that’s the all-American lesbian,” I explained.

My father shook his head in a familiar way. It wasn’t a shake of disgust or disappointment. It was the gesture of a man who still used a dictaphone instead of a computer and knew he would never adjust to a rapidly changing world. “I just can’t figure this place out,” he said.

My first weekend going away with Piper seemed innocent enough. The plan was that we two good pals, neither of whom theoretically had any romantic interest in the other, would drive up the coast, check into a B&B, and kick back for a night. When I shared this weekend agenda with my roommate, he was dubious. Hadn’t I fucked up a number of female friendships already in the messy year that I’d been single? (Yes.) What’s the big deal, I countered—Piper and I had slept in a bed together multiple times after nights of excessive drinking, all without incident. One night away? Piece of cake.

“Larry,” he said to me like a stern father, “remember: She’s a lesbian.”

I tried to. But when you’ve been sitting across from the coolest, hottest woman you know in the dining room of the Boonville Hotel in Northern California, having the best time in your life, and find yourself doing things you’ve never done before, like ordering port, things get cloudy.

The drive home the next morning was awkward. I was sure we were not going to be lovers and wondered if we would still be friends.

The following year I went to the desert arts festival Burning Man with garbage bags full of ready-to-burn wicker baskets from my apartment’s walls and 20 friends who comprised our new theme camp, Motel 666.

Over the next three days, I learned about the genius of the gift economy (nothing for sale; everything for trade); met the then-unpublished author Jonathan Lethem, who gave me a galley of his first book, Gun, With Occasional Music (wish I’d kept that); and began to become the adult person I was meant to be. And I shared a tent with my new girlfriend, Piper.

That fall I wrote a story for P.O.V. about the festival and ended it with a series of responses to the question, “What does Burning Man mean to you?” People said heady things like: “It’s like Yom Kippur, a day of atonement, only you don’t have to fast” and “It’s a symbol of destruction that can make way for creation.”

Piper’s response? “In the end, I think everyone just likes a topless girl on a bike.”

I’m not sure if that’s the moment I knew Piper was the girl for me. Or if it was when she told me that she was tempted to sleep with me just to shut me up about another woman I was obsessed with, whom she had decided was not worth my trouble. But the moment I was hooked forever was probably during a cross-country trip we took when we decided to move to the East Coast together. After a few days in Kansas City, we were set to hit the road toward Louisville when she told me she required one last stop at Arthur Bryant’s for a slab of ribs for breakfast that we could eat in the car. Shortly thereafter, she turned to me and said, “Baby, would you pop open a beer?”

The freedom of that road trip, and our first year back east that followed, was about to come to an abrupt end. Twenty minutes after saying “We need to talk,” Piper appeared in my office. The look on her face told me whatever was going on was about her, not me.

She pulled me onto the building fire escape. “You know how I told you I worked for an international art magazine after college?” I did remember, but she had always been vague about that time in her life.

Against everything in my nature, I had not pried about this unclear, seemingly lost year traveling the global art world with a girlfriend she never talked about. Her post-college year sounded cool, but all she’d said was that it was “not a great time in my life.”

I knew nothing about everything she was about to tell me: A story that years later would be told by Piper herself in a book translated into 20 languages, a story that would stream to millions of people across the world.

I don’t remember the exact first words I said on that fire escape. But the scene that played out before us was pretty close to what happens between Piper Chapman and Larry Bloom in the first episode of Season 1 of Orange Is the New Black. I didn’t say, “Are you fucking kidding me?” Clearly she wasn’t. The blood did not drain out of my body leaving me lifeless, nor did I lose my mind and start screaming. I didn’t, like Larry Bloom, exclaim, “Who are you? I feel like I’m in a Bourne movie! Have you killed?” But I wish I had—it’s a great line.

She didn’t tell me everything about her secret past that afternoon—she feared that I could be called to testify against her if she did. But she gave me the mind-blowing broad strokes: Shortly after graduating from college, Piper fell for what she described as “a sophisticated older woman” who asked Piper to travel with her to Bali, Brussels, and beyond as she continued her part in an international drug cartel. Piper was led to believe she would not have anything to do with the drug ring, but rather simply be there to keep her girlfriend company, all the while enjoying fancy hotels, decadent meals, and other so-called perks of the trade. A few months into their travels, Piper was asked to carry a bag of money from Chicago to Brussels, which she did. Shortly after that she was asked to carry drugs, which she narrowly avoided. She broke up with her girlfriend, fled the scene, and relocated to San Francisco. Fearful that her life and possibly her family members’ lives were in danger, she told her parents a version of where she had been and what she had done. For many years her secret seemed safe.

Finally she was telling me for the first time.

As has now been seen on TV, with many of the same words I used that afternoon, I told her I loved her. I told her we’d deal with it. I told her we’d get through it together. She told me she needed to borrow a cell phone from a co-worker of mine in order to call a lawyer in case our lines were being tapped. Paranoia? Perhaps. An indictment does that to you.

The men in my family would not be described as brave. What we are is loyal, and we are good problem solvers. So I moved into trying, with as little emotion as possible, to help fix this thing. It would be years before we would tell my own father and mother anything about this ordeal. Right then I needed to talk to someone who could at least help us navigate the road in front of us, so I called Eric, a good friend and, more important, an attorney. He was a big networker and would surely know more than we did about good legal counsel in Chicago, where Piper had been indicted. Above all, he was available to drink at lunch the next day.

As Piper began to wind her way through the criminal justice system, we kept our situation quiet from all but a few intimates. This decision was both practical and emotional. The late ’90s swept Piper out of her career making infomercials and into the dot-com bubble. She was a creative director at an online agency that seemed to be sold and/or change names every few months. While her job often involved standing over a 20-year-old and making sure he coded instead of playing EverQuest, she wanted to keep it: It was important to stay busy to stave off thinking about the future. And we had mounting legal bills.

Then there was a consideration that cannot be overstated: If you know your friend or family member is very likely on her way to prison, the topic threatens to consume every conversation. Even the chats among the few people who knew what was happening were draining.

Perhaps the most annoying reaction was disbelief, as in: “Middle-class white girls don’t go to prison for old drug crimes!” It’s a sentiment that’s fucked up on multiple levels—probably because to some extent it’s true; because it implies we could buy our way out of the problem; and because I knew Piper was going to prison. I did not know when and exactly for how long until she appeared before Judge Charles Norgle on a cold December morning in Chicago in 2004, pleading guilty to a reduced charge of money laundering, and receiving a reduced sentence of 15 months in federal prison.

Piper was scared and angry and depressed. Scared because she had little idea of what to expect inside a prison. Information about the female federal prison experience was scarce—the early-’80s TV show Prisoner: Cell Block H and the memoir of Scarsdale diet murderer Jean Harris don’t get you very far. Angry because it all seemed like such a waste: a waste of government resources; a waste to remove a functional and now law-abiding citizen from society 10 years after the crime; a waste of the opportunity to have Piper do years of community service, such as working with addicts, talking to kids about her mistakes, or mentoring young women in trouble. Depressed because six years knowing you could be sent to prison at the drop of a hat will break anyone, even my unbreakable girlfriend.

I was mostly fine. There were moments when I thought about Piper’s decision to break the law and was furious. I wasn’t mad because Piper made a bad decision when she was young and stupid. I was mad because I did the math on all the time and mental energy consumed by the ordeal, and it was time we wouldn’t get back. There’s not enough meditation in the world that could make most men I know believe “everything happens for a reason” when you live under a cloud of uncertainty for so long, a cloud that you can’t help but think is pissing on your best years.

Even so, these feelings rarely came up when we were in the middle of everything. To be mad while she was freaking out before her departure or trying to navigate her new world didn’t seem like a fair fight. I may have become an angrier person during Piper’s time in prison, but I also became a more patient one.

As the actual sentence neared, we began what felt like both a coming out (“I’m a convicted felon…”) and a farewell party (“…who will be going away for a while”) as we told our larger circle of friends. We spilled the story to gaping looks, uncertain questions, and supportive hand squeezes. If we seemed calm, it was because we were both ready for her to get in and then out of prison and move on with our lives. We got good at these talks; it became a script we had down cold. I also realized that when you tell your friends a story like this one, they pick up the check. I started booking these get-togethers at better restaurants.

How our friends reacted told us as much about them as it did about us. Our friend Candace burst out: “No fucking way—I knew something big was up! A bunch of us thought you were in the CIA.” One of our most tough-love and Republican friends, Michael, could not have been more empathetic, and his mom was Piper’s best pen pal over the next year.

Over pastrami at Katz’s Deli, our friend Gary said: “I’m going to tell you a version of what I told married friends who recently found out that the wife had cancer. I told them no one should get cancer, but if any couple could handle the challenge, it was them.” In other words: Honey, if any couple has to have a spouse go to prison, it probably ought to be you, because at least your friends all know you’ll be okay. He looked at me, and we all looked at each other, nodding in tacit agreement: Larry, on the other hand, wouldn’t do so well in the pokey.

In the spring of 2013, I am watching an advance screener of the soon-to-be-released Netflix show Orange Is the New Black, and a guy named Larry, who looks more like me than not, proposes to a blue-eyed blonde named Piper, looking like the younger cousin of my wife. They’re on a beach, as we were when I proposed, and he removes a ring from a sealed plastic bag, as I did. Larry Bloom, in one of his best lines, explains: “I gotta lock this shit down before you leave, Pipes.” I’m pretty sure it’s something I said, too, and even if I didn’t, it’s the scene at which my friends dropped their vocal opposition to Jason Biggs. For the record, though, I have never called her “Pipes.”

When Piper optioned her book to Jenji Kohan, the creator of Weeds, a number of people were asked to sign over something called “life rights.” In short: Some version of our lives could be depicted on the show, and we each agreed not to sue its creators if, for example, the character based on one of us was depicted as snobby, dopey, bitchy, overbearing, short, whatever. There’s a tremendous amount of trust that Piper had to put in Jenji.

If the show was unrealistic, salacious, or just plain bad, it could tarnish Piper’s book, a serious, accessible, and largely sex-free window into the women’s federal prison system. It was also a memoir written by a reluctant memoirist. Piper is a private person who told her story because she believed she could get a lot of people to pick up a book about prison who probably wouldn’t otherwise. Through this “Trojan horse” protagonist who might remind them of themselves, their daughter, or their niece, readers would get a peek into the diverse and complex world of women in prison: who they are, what happens when they get there, and what kind of world they’re dropped back into when they are released. The reaction to the book Orange Is the New Black gave Piper an opportunity to speak out on criminal justice reform—an opportunity very few prisoners have. The decision to give such a personal work over to a stranger—albeit an Emmy-winning one—looks easy now. Back then it wasn’t.

Piper’s instincts are great (with, um, one certain huge exception), and she is not risk-averse. She liked Jenji a lot and trusted her to do right by her book and the issues it brings up, while doing what Jenji Kohan is paid to do: make compelling television. And we trusted Piper. So we all signed the form. The one exception was her brother, who always likes to go his own way.