Growing Up Gloucester

What a teen pregnancy scandal looks like when some of the pregnant girls are your best friends.

gloucester teens

Photo by Erica McDonald

Stuff was different before. It used to be that on summer Fridays, Kaila Simpson would push the limits of the “No Loitering” sign in the McDonald’s parking lot near Gloucester High. Or she’d catch a ride, head down Main Street and past the pier to the Dunkin’ Donuts at the Stop & Shop where her cousin works and where Kaila can score discounted Milky Way hot chocolates, the most delicious drink in the whole world. Kaila lives for summer. She sunbathes with friends at Good Harbor Beach and watches the sunset from the old cannons at Stage Fort Park. At night she and her friends will sometimes go hang out in Rockport at Steel Derrick Quarry, which is deep enough into the woods that the cops can’t break up whatever boozing or fighting is going on.

But today was no ordinary summer day. Kaila, who had just turned 17, was set up at her round, oak-looking kitchen table. And she was even more distracted than usual by her pink Razr phone. Each time it bumped to the tune of Usher’s “His Mistakes,” Kaila would slide off her chair and scamper across the living room in search of clearer reception, leaving a trail of Paris Hilton perfume in her wake. At the window, Kaila raised her normal voice a full octave to offer a drawn-out “Hellooooo,” filtering the happy sound through a wide grin.

This time, it was NBC on the line. They wanted Kaila, along with as many of her pregnant and teenage-mom friends as she could help them find, to appear on the Today show. Chin down, head glued by the phone to her right shoulder, grin still intact, Kaila stroked her messy blond side ponytail as the producer hit her with the full pitch: They’d fly her down to New York, put her up in a fancy hotel, do her hair and makeup. And, on national television, Kaila would wow millions of people with her story. Sounded like a sweet deal. But Kaila had something else in the works. Letting the producer down gently, she told her no thanks.

The better offer Kaila was sitting on was from The Tyra Banks Show. Kaila, you see, feels a bond with the diva supermodel host. She knows they both can be goofy and tough and sexy and real, and therefore had promised the Tyra show her exclusive.

The calls rang in all afternoon. Some from other TV producers and newspaper reporters, others from relatives and friends of the family who’d seen Kaila in that morning’s Herald. That little article would be only the beginning of her stardom, she assured those who called, in a voice that wavered with the kind of excitement normally reserved for discussing the Jonas Brothers, whose pictures she’s taped up in her bedroom. That night she would be on Channel 7. And soon, of course: “I’m going to be on Tyra!”

The Herald had gotten its story when reporters spotted Kaila and a couple of her friends with babies in tow strolling a stretch of waterfront sidewalk known as the Boulevard. It was from these reporters that they first heard there was some sort of pregnancy pact among the girls of Gloucester High—which they, being girls of Gloucester High, found totally bizarre. Things got more intense when they got closer to McDonald’s, where a Channel 7 news team had camped out. “Like they were sitting there waiting for people with carriages to walk by,” Kaila remembers. “They just whipped out their cameras and started rolling.”
And that’s when Kaila did what she usually does, and took charge. In the clip that ran on Channel 7, she struts across the screen pushing a stroller. She is asked what parents can do to solve this pregnancy “epidemic.” Her hand clenching a cigarette and swatting the sun out of her eyes, she replies, “Get into their kids’ lives. Half the parents around here have no clue what’s going on with their kids.”

All the attention was somewhat intoxicating. Also strange—though this strangeness only made it more alluring—since, as Channel 7 had failed to mention, Kaila herself was not a teen mother or mother-to-be: The baby she’d been pushing was her one-year-old niece. Her real role in the whole drama was as her pregnant friends’ spokeswoman. She had always been the popular girl within her crowd, the kind of kid who sets the nightly social agenda and orchestrates the matchmaking between her friends and the older boys. Why shouldn’t she also be a quasi-agent when the press came calling? Her friends had enough to deal with. This was how she could help. Plus, the way she saw it, she could share the limelight without actually being saddled with a kid of her own. “I know how they are and how they think and everything,” Kaila says. “I basically say what they’re feeling about things because I know them so well.”
So yeah, stuff was different. But it was going to be cool.


Back in March, people had begun asking questions. School officials had counted up the number of pregnancies that year at Gloucester High and got 10—which was six more than last year. By the end of the semester, the number had risen to 18. When Time magazine looked into the story, principal Joseph Sullivan told its reporter that the phenomenon was a result of a pact. By the time the town’s mayor, Carolyn Kirk, and the school superintendent, Christopher Farmer, held a press conference five days later to tell the world there was no evidence of any such thing, none of that mattered all that much. Whether or not they had made a deal to get pregnant and raise their kids together, the fact was that 18 high schoolers were going to be mothers. Reporters had a field day stirring in pop culture references—Juno, Knocked Up, Jamie Lynn Spears, Nicole Richie—in an effort to provide answers.

Proof of just how insatiable the interest had become was in the backpack full of cash that a couple of National Enquirer staffers lugged with them as they wandered around town, looking for angles and info. Many of the girls had clammed up, following either their parents’ instructions or the school’s orders not to talk to the press. Pretty quick the Enquirer (and a lot of other media outlets) figured out that it was Kaila who held substantial sway with several of the teen moms. This was how the note reading, “Willing to pay to speak with Kaila Simpson,” came to be taped on the front door of her family’s apartment, and why a reporter from the tabloid and her gray-haired photographer friend ended up there not too long after. Unbothered by journalistic norms forbidding the practice, the duo from the Enquirer handed Kaila $200, for which Kaila introduced them to her best friend, Alivia, one of the Gloucester 18.

Alivia is 17, with a petite frame and startled-looking, sparkly eyes that make her appear much younger, and she gets nervous around strangers. Kaila was thrilled to hook her up with the kind of opportunity Alivia never could have brokered for herself. That’s what friends are for. After receiving $500 for an interview, Alivia showed up on the cover of the Enquirer‘s July 7 issue, holding her six-month-old, Xavier. The headline was “WE WANTED TO BE LIKE JAMIE LYNN.”

But of course the notion that a baby would make their lives anything like that of Jamie Lynn or Britney or any other celebrity is crazy. In Gloucester, young mothers push carriages down the Boulevard, the mile-long promenade along Gloucester Harbor. The benches that line the sidewalk provide a good place for changing diapers, and for letting admirers who pass ooh and aah over the cute babies. These strolls often begin or end at the parking lot shared by McDonald’s and the 7-Eleven, right across from the Maplewood housing project. On summer afternoons, the lot is a hot spot for socializing; sometimes it’s a kind of battlefield as well. Kaila’s ex-boyfriend Kyle was stabbed in the gut and nearly killed here in March, and catfights are no novelty, either. Plenty of the kids here—and they range in age from eight to mid-twenties—come from families with fisherman fathers who are out to sea for weeks.

They come here because there’s nothing else to do. There aren’t many summer jobs in Gloucester, not even for the student council kids (who don’t hang out here). Some of the parking lot regulars will finish high school, but if that doesn’t happen, it doesn’t happen. When it comes to school or the future or whatever, you do what you can. The attitude’s the same toward getting pregnant—an “unplanned blessing,” the girls call it.


When Alivia first told Kaila she was pregnant, it didn’t feel like a scandal to them. It was just a high school girl getting pregnant. Sure, there were a few tears; they knew their lives would change. But the girls weren’t devastated. Alivia had seen lots of her peers become mothers and the challenges didn’t seem impossible. In fact, there were parts of motherhood that seemed exciting. Alivia came to think that this would be a chance to have a family of her own, which is something she’d always wanted. She’s never met her father, and her mother only surfaces once in a while. The grandmother she used to live with died a few years back, and so Alivia moved in with an aunt, who subsequently died of a heroin overdose. From there it was on to another aunt’s house.

Alivia was sure it was love that she felt for the father. He was 21, a Brazilian immigrant, and she was attracted to his maturity and his sense of humor. Before he and Alivia got together, he and Kaila had hooked up. But any awkwardness between the girls had long since disappeared—Kaila and Alivia were too tight to let any boy get in the way. He was the first person Alivia had ever slept with, and when he took the news of the pregnancy with a smile (“He tells me that girls have babies in Brazil at 13,” she says), Alivia felt pretty good. She fantasized about getting an apartment with him.

Not long after Alivia and Kaila had started telling people, their friend Meaghan pulled Alivia aside during math class. Meaghan wondered what it was like to be pregnant. When she admitted she was going to have a baby, too, it was a relief for Alivia to know she had a friend in the same spot. That’s when they made an agreement (sort of like a pact, maybe, if you wanted to twist it that way) to raise their babies together. Meaghan had grown up with Kaila and Alivia in the Maplewood projects. As kids they all played arcade games at Bonkers and Good Times before graduating at some point to scrounging for littered cigarette butts to smoke. In elementary school, they practically memorized their favorite movie, Riding in Cars with Boys, in which Drew Barrymore plays a girl who gets pregnant at age 15 but still manages to make her dreams come true. Raising families would be the next experience they could share. They’d stroll together on the Boulevard—Kaila could bring her niece, Kaycie—and it would be great.

After school, Kaila and Alivia worked at McDonald’s, where their managers made sure to schedule the chatty friends for different shifts. The work could be tough, especially for a pregnant girl. One afternoon Alivia passed out in the kitchen while working the apple pie oven. She later angered her bosses when she said she could no longer lift the heavy fryers that had to be taken apart for cleaning at the end of the day. A few weeks later, Kaila phoned to say that she couldn’t come in the next day, that Alivia had gone into labor prematurely and she needed to be with her. They told her not to come back.

Alivia’s son, Xavier, was delivered by emergency C-section nearly three months before he was due. (There are higher risks associated with teen pregnancies because, as a group, teenagers are less likely to eat and sleep and care for their bodies the way obstetricians advise.) Doctors rushed the baby by ambulance from the North Shore to Children’s Hospital in Boston; later that night, Alivia, still woozy from the surgery, was shuttled to Boston in an ambulance with a couple of friends. “I didn’t know what was going on,” she remembers. “My friend in the front seat put on Jam’n 94.5. It was like a party.”

Xavier had a list of health problems so long and severe that the doctors weren’t sure he would make it. He’d been born with a hole in his heart, bleeding in his brain, and cysts in his airway. To Alivia it seemed as if the doctors were also wondering how far they should go to save him. “They said, ‘What do you want to do?’ And I didn’t want [Xavier] to hurt his whole life,” Alivia says. The boy’s father insisted that every effort be made—a bit of parental dedication that Alivia now finds ridiculous, given that his parenting has been almost totally hands-off ever since.

The next day Kaila hurried down to the hospital, where she’d visit Alivia regularly for the next three months. “I thought I knew what it was going to be like,” Alivia says. “But his medical issues—it’s been more than normal.” Though Xavier was released from Children’s last spring, doctors are still uncertain what complications he’ll face as he gets older. He may never be able to walk. He may be slow. It’s just too soon to tell.

These days, the baby’s father sends Alivia $150 a week, which helps buy the cute Calvin Klein onesies and plush bibs that she considers important. But mostly she relies on government assistance to pay her bills. MassHealth covers medical expenses and childcare necessities like formula. The state also pays for Xavier’s place at the daycare center at Gloucester High School (a program, as you may have read in the breathless scandal coverage, that is a lightning rod for critics, who say that free childcare at school is exactly the sort of thing that encourages high schoolers to get pregnant in the first place).

The girls joke that Kaila is Xavier’s father. When she baby-sits, she shows him off as if he’s her own. When the three of them are together, it’s often Kaila who feeds him and changes his diapers. On her wall at home, Kaila has put up photos of Xavier alongside pictures of her niece, Kaycie. Sometimes Kaila and Kaycie meet up at McDonald’s or Burnham’s Field with Alivia and Xavier, as well as Meaghan and her baby boy, Jayden. Then they stroll the Boulevard together, the way they always talked about.


On the Saturday after Time dropped the P-word, Kaila and Alivia made sure they were prepared for what was coming. They set out for an afternoon on the town dressed so that if they met a photographer, they’d look camera-ready. Kaila pulled on a denim skirt and a glittery, cream-colored tube top that left her white bra straps exposed. Her hair was almost completely straight, the product of a lengthy session with the flat iron, and she swung a very real-looking faux Chanel bag. Alivia, with her hair perfectly slicked back, wore Bermuda-length jean shorts and a low-cut scoop-neck shirt. Right off the Boulevard, down near Main Street, Kaila caught sight of a small carnival in a parking lot. “Oh my gosh,” Alivia said breathily. “I want to do the slide so bad! I looooove slides.” It was an inflatable number, the kind that makes elementary schoolers lose their minds. She dug up some loose change from Xavier’s carriage, and the girls each took a turn.

After her trip down the slide, as she walked back toward Alivia, Kaila was intercepted by a woman in cutoff jeans. “Are you Kaila Simpson?” she asked. She was a reporter from New York with a photog in tow, and she said she’d heard Kaila was the girl to talk to. After feeling them out for a few minutes, Kaila decided they were bad news and she wasn’t interested in an interview. Just then, a man working at the carnival shooed the reporters away. This, he told them, was a place for children.

An hour later, in Kaila’s living room, Alivia was shouting into the phone. “I feel like Britney Spears!” A girlfriend of theirs, who was spending the summer with her family in Brazil, had called to inform them the Gloucester girls had made the news all the way down in South America. Kaila and Alivia floated the idea of going to Brazil for a visit. (Kaila says she can understand Portuguese well, but can only speak it when she’s drunk.) The trip would be expensive, but they were sure they could find a way to make it work. Then, Kaila paused: “Who’s gonna watch Xavier?”

At that moment the baby was lying contentedly on the gray carpet, surrounded by toys and DVDs, while Alivia perched above him from her usual spot on the arm of the couch. Kaila’s family had moved into this three-bedroom unit in Pond View Village two years ago, when the housing complex had just opened. It sits in West Gloucester, about a mile from the Boulevard, and it used to be a glue factory, haunted, goes the story, by the ghosts of dead horses and disgruntled factory workers. To Kaila, the place still feels new.

It also feels full. Along with Kaila and her mom, there’s her 12-year-old brother, Cody, who quarterbacks his rec-league football team. And though Kaila and Cody’s parents split up three years ago, their father, Victor, still bunks at the apartment whenever he’s not off fishing. For the past several months, Kaila’s friend Erin has claimed the living room couch as a bed. Erin’s father, who she considers way too controlling, lives in Rockport, and her mother’s out of the picture.

Earlier this year, Erin tried to get pregnant. “I wanted a baby,” she says. “I don’t have a mom or a dad around. I wanted someone who would be there for me, who would love me completely.” But Kaila’s mom, Sally, who Erin and Alivia and plenty of others also call “Mom,” ultimately talked her out of that.

Sally is stick-thin with long, bleached-blond hair. She’s spent all of her 47 years in Gloucester, and having had her oldest daughter, Charity, when she herself was only 17, she understands what Kaila’s friends are dealing with. The parenting style Sally has developed is more hap-hazard than your typical PTA president’s, but she seems to truly want her kids to have it better than she did, and so she does what she can. Until she was laid off this summer, she put in seven days a week as a supervisor at a cleaning company. Now she’s working toward her high school degree—something she put off years ago. “I see the kids go out, and still to this day I say, ‘I never had it, I never had a teenage life,'” Sally says. “I like to have the kids around and listen to their stories and watch movies.” No topic is off-limits, not drugs or fighting or sex. Sally knows she’s not perfect, but by at least one important measure in Gloucester, she’s succeeded. Charity didn’t have children until her mid-twenties. And so far, so good with Kaila, who adds that her mom is “obviously doing something right. I’m 17. And no babies!”


As the summer wore on, Kaila got more and more pumped about meeting Tyra Banks. “I was wicked excited,” she says. “Are you kiddin’ me? I love Tyra. I watch all of her shows.”

Banks’s people had first reached Kaila through her MySpace page. Fishing for a blockbuster sit-down with one of the Gloucester 18, the show was happy to put Kaila in front of the cameras, too, if she could deliver her pal Alivia as she had for the Enquirer. They set a date to tape the show in early August, a month after the girls’ close friend Lindsey, who’s due this month, appeared on Good Morning America with her boyfriend. (There were rumors that the couple was also talking to the creators of TLC’s Jon and Kate Plus 8 about a reality show.)

Holding out for Tyra, which had been on summer hiatus, was Kaila’s idea—and one she never questioned. By the time the show called in the first week of August to make travel arrangements for Kaila and her mom and get clothing and shoe sizes, Kaila had been daydreaming about the experience. How tall would Tyra be in real life? she wondered. How would Tyra’s hair be styled on this episode?

But two days before the taping, Kaila got a call to tell her that she wouldn’t be needed. All along, she’d quietly feared that Alivia’s aunt would refuse to give the show the consent they needed. Kaila couldn’t help but feel resentful—she had been there for her friend in a way that she felt Alivia’s aunt never had. Meanwhile, behind the girls’ backs, Alivia’s aunt had made her own deal with NBC for Alivia to appear with Dr. Drew Pinsky and Hoda Kotb on a network special. For the taping, the aunt and a friend of hers were flown with Alivia to New York. The show aired on August 6. Kaila didn’t bother to tune in. When she thinks about it now, it all seemed too cool to come true anyway. “I don’t really let things bother me,” she says, taking some pride in her toughness. “I used to.”

On the day before the start of school in September, Kaila and Alivia hung out on the sidewalk in front of the Maplewood projects, playing with Xavier and talking about nothing. Tomorrow would be Alivia’s first day as both a high school student and a mom. Xavier, who’s now nine months old, will spend it in the school’s daycare; Meaghan’s baby boy will be there as well. But Alivia doesn’t want to be associated with the other teen moms. She doesn’t want them to be seen as some kind of clique. At 17, she’ll be taking ninth- and 10th-grade classes and is already wondering if she can juggle school and her boy. “Maybe I’ll just get my GED or something?” Alivia said, her face wrinkled with anxiousness.

Kaila had on tight dark jeans, black wedge heels, and five different pieces of glittery jewelry. School was the last thing on her mind. She didn’t return to Gloucester High after last winter break, for what would have been the second semester of her sophomore year; she needed a break from so many of the stuck-up girls who wouldn’t mind their own business. Plus, Kaila hated studying and had plenty of beefs with school administrators over the sorts of classes she should be taking. Even before the whole pregnancy-pact thing, she was no fan of Principal Sullivan. After it, Kaila despised him for assuming he understood her friends. “Like, who is he to open his mouth and say something like that?” she steams. “I don’t know who he thinks he is.” When Sullivan left his job over the mess in August, Kaila was thrilled. She’s now trying to convince the interim principal, William Goodwin, to let her into a smaller special-ed program, where she would enjoy shorter school days and less homework. She’d start in a few months, and whether she graduates from high school or gets her GED, Kaila figures she’ll ultimately become a beautician. Or maybe a nurse. Or something else.

As the wind picked up a bit, Alivia wondered aloud if Xavier was cold, and whether she needed to feed him. Fall felt like it was coming on, and it had gotten Kaila in an unusually reflective mood. Looking back at the summer, she had no regrets. “Everything happens for a reason. That’s what I think.”