Jane Pratt’s Perpetual Adolescence: Why She’s Still Talking Teen Three Decades After Sassy

Photo: Lucas Michael/New York Magazine

Jane Pratt has been 15 for an awfully long time now.

She calls that her “emotional age,” and she thinks we all have one: It’s the time in our past that we can’t entirely let go, because of something that happened to us then. Ask her and she’ll guess yours, along with your birthday (this is a trick she sometimes does with callers to her Sirius satellite radio show). You see, she describes herself as ­being “psychic-intuitive,” which is something like having ESP. Not long ago, she tells me, she guessed the emotional age of one of her employees and it turned out that was the year she’d been raped. After we talked in her office for two hours, at her latest venture—an online women’s magazine called xoJane—she told me that she’d put mine at 13. And maybe she’s right, and I’ll always be that lonely kid in a new school.

Or just as likely, Pratt knows that a lot of us have felt that way and don’t really get over it, but form ourselves around that hoarded trauma. Whether or not this comes by way of paranormal talent, it’s a great insight, and the reason why Sassy, the nonconformist’s teen magazine she was hired to edit when she was just out of college, in 1987, was so beloved. Her Sassy understood. It was confessional, confiding, a bit reckless, swooning for the authentic pop anti-hero, and surly about anything phony. It talked about things that were parts of people’s untidy lives but often, out of shame, remained undiscussed (“My Mother Was a Coke Fiend”; “My Best Friend Died of AIDS”). It didn’t just reflect the way that youth culture was going—Sassy’s journalistic approach could be summed up in its rubric “It Happened to Me,” which she still uses, on xoJane—but helped get us there, to the blog-and-tweet society-of-the-spectacle-of-the-self we live in today. (It also crowd-sourced from its readers, quaintly, via the U.S. Mail.) By being so early and deft with its understanding of self-revelation, Sassy inspired a cult: To this day, many women between the ages of 30 and 50 (and a lot of gay men, too) will tell you that Sassy was the first magazine that ever felt like it was actually telling the truth. Years after the magazine closed, Farrar, Straus & Giroux—of all ­places—published a history of the magazine called, with complete sincerity, How Sassy Changed My Life.

Pratt foresaw “the beginning of the Facebooking of our culture, the dawn of the age of oversharing,” says Bill Van Parys, executive editor of Jane, Pratt’s bit-more-grown-up second magazine, which she started in 1997. Van Parys describes Pratt’s editing technique as the opposite of what a traditional news edit goes for. “She was always interested in the emotions and the insecurities,” he says. And “she was also willing to do something that was totally wrong.” They put a cover line on Jane that said, based on a study mentioned in that issue: “Yet another reason to not give up smoking: You could get acne!” he remembers. “We were eaten alive.” As another ex-Jane staffer put it, “She understands and accepts you being crazy because she is crazy. And that makes you feel close to her.”

THE LOW-COST and brightly painted offices for xoJane are on Fifth Avenue and 28th Street, and the place does feel like a pajama party, much as Sassy’s offices probably did. Pratt, who maintains a friendly hint of her North Carolina drawl, laughs encouragingly and affirmingly and often. She’s wearing a black Phillip Lim dress she’d bought for her friend Courteney Cox, who was ­photographed in it at an event and gave it back to her since she couldn’t wear it anymore. We’re in the middle of this summer’s ominous monsoon season, and Pratt says, “I like it. I like natural disasters.”

She started the website a little over a year ago, and it’s dominated by tell-all first-­person voices: “Will My Student Loans Keep Me From Ever Finding Love?”; ­“Beauty Products for When Depression Eats You Alive”; “I Found Out About My Sexual Assault Because Another (Female) Co-worker Took Photos Through the Car ­Window While It Was Happening”; “Gonna Wash That Angel Dust Right Outta My Hair: ‘Miracle’ (Uh-Huh) Treatments to Help You Pass Those Follicle Drug Tests, Naughty Nancys!”; “It Happened to Me: I Had a Baby With My Husband’s Best Friend”; “It’s Happening to Me: Right Now, I’m Miscarry­ing a Baby.”

Creating a young women’s online magazine was originally something she was doing with an actual teenager, the hyperbranded blogger Tavi Gevinson. After all, Pratt might be emotionally 15, but until six months ago, she’d not bothered to tweet, and reads links to her “ladyblog” competitors only if they’re forwarded to her. In other words, the Tavi plan was a good way for her to comfortably align herself with the ­Internet-bred youth. But when Pratt partnered with Say Media to produce the magazine, Tavi and her dad couldn’t come to terms with Say, and backed out. Now Tavi has her own site, Rookie (a partner with New York Media). On its masthead, Pratt is listed as its “fairy godmother.”

xoJane takes the confiding tone of Sassy and Jane and puts it on the blog-age assembly line of fifteen posts a day, many of which, to Pratt’s dismay, she can’t even read before they go up. Her iPhone screen continually lets her know just how many people are reading each story (xoJane claims a respectable 800,000 unique visitors a month). The readership metrics translate into how much money the site makes. “I live by them now,” she says drily, of the numbers. “And always knowing them makes her so pleasant to be around,” jokes one of the women on laptops chatting in their cluttered work space. There are six or so writer-editors on the site. With all of the part-timers and out-of-the-office writers feeding the site’s content, Pratt’s not even sure exactly how many people work for her.

At Sassy and Jane, writers were “cast” for their roles in the magazine, making it more like a sitcom with characters that readers could become invested in. It’s harder to do that with so many people filing from all over at xoJane, which can at times feel more like an all-talk-radio program (tune in and hear the overshare!) than a plotted television program. “I hope that there’s enough written by who I consider the key characters that I’m wanting to build,” she says. “So that people feel like they do know the main characters and are following their trajectories.”

Of course, the biggest difference between Sassy and xoJane is that Pratt is no longer the same age as the women who write for her, and her life is no longer that similar to the lives of those that read the site. She’s ­xoJane’s 49-year-old cool mom, who goes home at the end of the day to hit a yoga class and spend time with her 9-year-old daughter, Charlotte, and their dog, Balloon, not the 24-year-old she was when an Australian magazine company plucked her out of ­entry-level obscurity to launch the American edition of their teen title, called Dolly there and Sassy here.

Then, her job was to be Jane, and she never punched out: Editing for her was a New Journalist Dumpster dive into Reality Bites–era celebrity and grunge glamour. This was partly because landing the leading role at Sassy made her young and famous too, and she didn’t seem to be conflicted by any newspaper-y notions of her observer status. The other Sassy editors were amazed by the ease with which she took to this stardom. But they were all expected to live in this cool world their readers wanted to be a part of, too. Sassy’s pink offices, on Times Square, became a clubhouse for the magazine’s friends—the leading lights of Generation X, like Sonic Youth. Its “Cute Band Alert” page was rigorously curated. Chloë Sevigny was an intern. Pratt was often gabbing on the phone with Michael Stipe, whom she met when she was in college by chasing after R.E.M.’s bus following a show. (They still talk or text daily.) Remember her “emotional age”? Well, she told a reporter at the time, she was finally the popular girl she’d never been at 16.

These are some of the things that happened to her: Pratt worked relentlessly, never sleeping much. Eventually Sassy ran into problems when it was boycotted by the religious right, scaring off some of its advertisers. It pulled back from writing about sex and lost some of its freewheeling sure-­footedness. Pratt was offered a TV talk show, which at first was seen as a way to promote the magazine: Sassy, after all, has something in common with Oprah and Jerry Springer. Pratt was less and less around the magazine’s office. Eventually she stepped down. Unfortunately, the TV show didn’t last, and neither did a second one. 

So she went back to being an editor, this time shopping a new magazine wrapped in her foundational tell-all premise. Jane magazine ended up at Fairchild Publications, home of W and Women’s Wear Daily. She hired Van Parys from Rolling Stone, and then she set about casting a new staff. “She was always very up front about that,” Van Parys says. “That was the way she viewed the hires: the character in the ­series. We had people who played in bands or made clothes. We didn’t want traditional people; we wanted freaks with a point of view and talent.”

It made for an unusually uninhibited office environment, with Pratt encouraging staffers to push past their own boundaries. Because she seems nonjudgmental and wants women, above all, to never apologize for who they are, many people describe working for her as “therapeutic.”

But one of the ways the web is different from a monthly magazine is in how quickly something can be noticed, memed, celebrated, and deplored—moved well beyond the control, or full awareness, of even the most quick-thinking editors. One of Pratt’s hires for xoJane was a woman named Cat Marnell, who until a few months ago was the site’s beauty and health editor, although she mostly wrote about her bleak, enthusiastic drug use. Pratt says she didn’t necessarily want the healthiest person in the world for the health-editor job, and liked Marnell’s writing. “I was also interested in the fact that Vice magazine has a writer who tries different drugs and writes about that, and I was thinking, You don’t usually see a woman do that; you hear about it more ­after the fact, you hear of it after they’ve gotten sober or whatever.”

When Marnell actually came into the office—which wasn’t too often—she sometimes could be overheard trying to score. She also spent a great deal of time in Pratt’s office, talking and talking. “From a writing standpoint and a character standpoint, I wanted there to be an arc to this,” says Pratt, sounding like she was speaking of a plot, not a person. “She should be heading toward something. And she was, at one point. She wrote about getting off Adderall and Xanax and stuff like that. And I felt like people were going somewhere with her.”

Pratt says that she did her best to help Marnell, and got more personally involved with her than she probably should have. But she comes off more like a peer of Marnell’s than a boss. “I actually feel like people can do whatever the fuck they want, you know?” she says. Drugs? She’s done plenty of them herself, yes. And she knows lots of people who have gotten themselves in various sorts of addiction trouble, and many who have gotten out of it again. She even has, in her loft, an infrared “Scientology sauna” to sweat out toxins: Apparently, in that light, smokers sweat blue-black, she says, and users of hallucinogens, purple.

When I talk to Marnell on the phone one night (she asked that I call her before she started “smoking dust” so that she would be coherent, which she was, though her dealer’s call did interrupt) she seemed to miss Pratt. “She’s a total libertarian, fabulous like that,” she says. “She just really appreciates creativity. People think, Oh, she was enabling you. But she was just letting me be flawed.” Now Marnell has a column for Vice,Amphetamine Logic,” and a hustling book agent plugging her future memoir (“game-changing … our nonfiction Bright Lights, Big City”), so her job is to be fucked up.

The Marnell caper was, in some ways, a success; Pratt had been out of the game for a while (she left her now-shuttered eponymous ­magazine in 2005), and it got people talking about the site. “What a stunt,” says Van Parys, admiringly. “Good old Jane. She knows who to hitch her wagon to.”

“It didn’t surprise me that it became that big a deal,” Pratt says, “because that was part of what I had hoped—that people would ­really identify with her and like her writing as much as I did. How quickly it happened—well, I guess that’s the Internet, right?”

If you ask, Pratt will tell you that her great passion is documentary film—she made a couple before her career took off, and documentary is pretty much the only kind of film she watches for pleasure. Her TV diet consists of the Real Housewives of Beverly Hills and Dance Moms, which she watches with her daughter. This says something about what it is to look through her eyes: fascinated, not judging. After she was let go, Marnell compared Pratt to Andy Warhol.

PRATT’S MOTHER, Sheila Blake, thinks her daughter never had much of a chance to be conventional. “Here’s how I see it: Her dad was an artist, I’m an artist. She grew up in North Carolina and went to a very progressive school. So I don’t think that Jane really knew that she was a rebel; that’s just what she grew up with.” Blake let her kids melt their crayons on the radiators to make pretty colors and walk around barefoot (once they went on a family trip to Washington, D.C., and didn’t notice Pratt didn’t have shoes on for three days; as a side note, Pratt lets her daughter walk around the city barefoot, which horrifies the other Tribeca moms).

Pratt’s grandfather Gaither Pratt was a paranormal psychology researcher at the University of Virginia and believed he had ESP; his final experiment was to try to get a message to the living from beyond the grave—the combination to a lockbox. Pratt is pretty sure she got it through the spirit channels, but she hasn’t yet made it to Charlottesville to test it. In an e-mail she also tells me that “if you take animal-glandular supplements that have porcine eye in them, you can see and sense things on other planes the way animals do—I am not even kidding. There’s one called I-plex that I believe a bunch of psychics must use.” Still, she saw fit to add: “I know that you can use this e-mail against me to make me sound like a total kook if you want to.”

Pratt’s father, Vernon Pratt, was a minimalist painter and, she says, suffered from various addictive behaviors and engaged in certain transgressive proclivities. He was also a bit of an adventurer: He would take Pratt on excursions down to look at the tranny hookers by the West Side Highway during their trips to visit relatives in New York. “I think that because of him I’m very comfortable around addicts and I’m naturally—well, when I read the book Codependent No More, I thought, Oh, my gosh, that’s me.

She also thinks of herself as a people-pleaser, which is why when her father got her to apply to his alma mater, Andover, and she was accepted, she went, even though she would rather have stayed home. That upper-crust world made her miserably alienated and self-destructive, but she returned the next year with a makeover and became popular. Then she went off to Oberlin, where she got to be a hippie again (“I thought, Oh, good, I get my daughter back,” her mother says) and minored in dance.

That’s where she met Stipe, after a show. “Her chasing after the tour bus and getting onboard with R.E.M., that’s the opening credits for the Jane Pratt movie. That tells you what you need to know,” says Stephen Treffinger, an Oberlin friend who’s remained close with her. He remembers getting up at 2 a.m. and seeing Peter Buck making out with one of his other housemates, and then everybody waking up hungover after passing out on the front lawn. To be an old friend of Pratt’s means that if you run into her in a hotel where you both happen to be staying in L.A., she suggests you go to a get-together nearby, and it’s a birthday party Courtney Love is throwing for Edward Norton, with ­Leonardo DiCaprio in attendance. Those starry nights were part of that seamlessness in her life. She and Drew Barrymore had a close friendship for a while, which was also reflected in the pages of Jane (Pratt doesn’t want to comment on all that talk about them being romantically involved at one point); Pamela Anderson was another friend of Jane’s and Jane. Van Parys noted that while her friendship with celebrities helped her in certain ways—magazines like Jane need famous faces to sell on the newsstand—it could also complicate things, since there was a personal aspect to contend with. He recalls that once Courtney Love sat for a cover shoot, but when the recording of Pratt’s interview with her didn’t come through, she wouldn’t call back for a re-­interview and they had to cook up a story-free cover.

Love was also one of the people Pratt suggested I speak to for this story, and she still isn’t the easiest person to reach. “Jane is a good friend for a long time,” she says when we talk (after I agreed, via e-mail, to not describe her as “troubled” or “controversial,” or Pratt as “eccentric”). “Right now there are so few people who live by a code with real honor to it. I can tell her anything and it’s not going to go anywhere—ever. She’s a vault.” This is important to Love, who has an unusual vigilance about how she’s perceived. “We’ve never sold either of us out.”

The two go way back. Sassy had Love and Kurt Cobain on its cover when they were just dating, and Pratt and Love once went on an adventure in Donatella Versace’s private jet to Venice from the shows in Milan after Love and Versace got in a fight. More recently, when Love was accused (in “Page Six,” of course) of “ruining” a townhouse she was renting in the West Village and threatened with eviction, Pratt had a friend take pretty photos of it and put them up on ­xoJane, which helped get the eviction case dismissed. “I could have been evicted and had the word ‘trashed’ on my reputation,” Love says. “And she fixed that.” Then Pratt helped her find a new place. “It would be nice to see her succeed,” Love says about xoJane—“be ­financially well off.”

Love and Pratt and Stipe hang out a lot together (“When dining with enormously wealthy rock stars, she goes dutch,” says Love. “That’s all you need to know.”) They’re part of what Love calls a “gang” that includes, among others, Mario Batali and Pratt’s Oberlin friend Julie Panebianco, who met Peter Buck around the same time as Pratt. Pratt, Stipe, Buck, and Panebianco used to throw a big Christmas party every year, though not in the past few. “The guest list would be Julia ­Roberts,” Pratt says, making a finger air check. “John F. Kennedy Jr.” Check!

From her home in suburban Maryland, Pratt’s mom has sometimes worried about her. It’s been an awfully long time since she got on that R.E.M. tour bus. “She’s maybe too accepting of certain cuckoo behavior,” Blair says. “She doesn’t have that kind of signal—Whoa, no, it’s not a good idea.” And she thinks that some of Pratt’s friends, like Love (but not Cox), aren’t always there for her. “Very good friends might not be very good friends at all. It might be just proximity,” she says. 

When I meet Pratt again, not far from her apartment in Tribeca, kombucha tea in hand, wearing Stipe’s hand-me-down Dior Homme T-shirt, I ask her if she has these edgier characters in her life to live vicariously. This would be a very documentary-filmmaker thing to do. But she doesn’t think so, noting that she’s been through quite a bit herself. Her father was killed under mysterious circumstances officially described as a hit-and-run; she developed pancreatitis as a side effect of her IVF and ended up on life support after miscarrying twins the same year that she was forced out at Jane and broke up with her longtime fiancée.

She thinks this is why she does what she does: “When I was a teenager and suicidal at boarding school—not literally trying to—I started thinking that this will at some point allow me to help other people going through this,” she says. “It’s the way my mind tricks itself. It’s what my mind does. As if it’s a separate thing. It goes into this mode of thinking, I’m going through this because it makes me better understand other people, and I’m going to be able to help them.

It’s “It Happened to Me” as a sort of theology of uplift, the sinners and the broken and the desperate all redeemed and repaired in some unapologetically cool, very all-bets-are-off communion. “I love talking to Courtney Love, I love talking to Cat. I love talking to Michael. It’s fascinating. I feel like, Ahhh, I’m with my people,” she says. “My weirdos.”     

It Happened to Jane Pratt