Once upon a time, p.6
Once Upon a Time, page 6
Did Carolyn’s distance from her father affect the way she responded to male attention in college? According to Wolf, “When people experience loss or difficulties in any major area of their lives, they can make decisions that are out of line with their true selves. Grief can cloud your judgment.”
Every child whose parents’ marriage has fallen apart is prone to wondering, Was it my fault? According to one Bessette family member, “William was closest to Lauren, a go-getter. Lisa was a little more distant, she was shy by nature. But as for Carolyn and [her father]… we don’t want to go there.”
Whatever distance Carolyn may have had from her father obviously did not extend to her father’s family, and specifically to the women in her father’s family. Aunts Dorothy and Diane were constantly pulling the Bessette girls into their orbit, a warm, lively environment where Carolyn was clearly comfortable being playful. In a late 1980s Bessette Christmas photo, her sense of fun is on full display as she throws her leg over her cousin and grandmother as they pose on the couch with Carolyn’s sisters. Another photo from the holidays shows the girls’ young cousin Abbi pulling Carolyn’s hair, whose mouth is open wide in surprise. Gatherings with these women occurred on a regular basis until the last months of Carolyn’s life.
“Carolyn was a handful,” the family member added, laughing.
What was it about Carolyn’s dynamic with her father that may have made her relationship seem noticeably different from, for example, his relationship with Lauren? Did William, an engineer described as “anal-retentive” and “detail-oriented,” see Lauren’s academic excellence as a more valued trait than Carolyn’s more sociable persona? Was he less comfortable around the more lively child?
Another close friend remembers Carolyn talking about the fact that there were issues with her father’s share of the tuition. Thomas Bessette said there was a “disagreement and eventually a butting of heads between Ann and Bill about where the girls should continue their education. Both wanted them to go and get degrees. The discussion was about at what college.”
Dana does not recall Carolyn’s father ever coming to Boston, but Dana met him when Carolyn asked for her company visiting him in White Plains. Dana remembers that he was tall, tan, and very good-looking, with straight, light hair. Carolyn rarely spoke of her father, and those conversations were generally prompted by the issues with his tuition payments.
“It was not the greatest relationship, not easy,” Dana says. “William was a civil engineer, out of the country a lot, travels presumably related to work. He never remarried, and lived in an apartment in White Plains, a step down. We visited him twice. She didn’t really talk about him, but she did feel he didn’t treat her mother well. And Carolyn was fiercely protective of her mother.”
* * *
HOWEVER MUCH FUN CAROLYN had—with boys, at the bars, even with schoolwork itself—she was not one to take even a single step back from her friendships. Dana lost her mother to cancer their sophomore year, and Carolyn “never left my side,” Dana said. “Never let go of me. It was amazing then and even more so thinking back on it now that a college student could be so nurturing during the death of my mother—[she was] incredibly caring.” Dana often went home on weekends after her mother’s death to nearby Medford, Massachusetts, where her father lived, and Carolyn frequently accompanied her.
In their junior year, Dana suffered another devastating loss, this time the death of her father. Again, Carolyn was there for her night and day.
Carolyn went with Dana to her father’s wake, both keeping vigil and remaining lighthearted, a bright spot in very dark days. At one point, Mr. Gallo’s godmother walked in, looked at Carolyn (who had relieved Dana from the task of greeting visitors), and said, “And who are you?” Throughout the day, over and over, the elderly woman said the same thing to everyone she met. “So for years after,” Dana said, “whenever we met someone and Carolyn wanted to make me laugh, she would say, ‘And who are you?’ in that same imperious tone. It sent me into hysterics every time.”
The back-to-back deaths of her parents were blows that nearly felled Dana, and she credits Carolyn with helping her navigate her emotions at the time. “I’m not sure I would be where I am today had she not held me up when I needed a true friend. She was selfless when I was a mess. She did it without any expectation of reciprocation. In the years following my mother’s and then father’s deaths, she would sit next to me and rub my head, hold my hand. A loving touch was always there.”
Carolyn’s den was inclusive; in addition to her friends, the girls ended up taking in a husky named Silver that had belonged to Dana’s father. Carolyn and Dana shared a room, and Silver slept with them. Unfortunately, as much as they adored the dog, it became clear that undergraduates living in Boston could not give Silver an ideal life. Their schedules were erratic at best, and the apartment had no air-conditioning, a very uncomfortable situation for a husky. Carolyn sobbed when they brought Silver to the airport, lightly sedating her before her flight to the farm in Utah where she would make her new home.
In their senior year, the girls moved again, this time next door to 1056 Commonwealth Avenue, a slightly nicer building considered off-campus housing. Throughout, Carolyn worried about Dana. On Dana’s birthday, near the end of senior year, Carolyn tried again. She showed up with a basket, on top of which was a red bow. Inside was an adorable black kitten, also sporting a red bow.
“You got me a cat, Carolyn,” Dana told her. “You know I don’t like cats.”
“Just give it a chance.” Carolyn held the kitten up close to them both, making squeaking noises. “But she’s so cute! Just look at that little face,” she said. “How can you resist?”
Dana did not resist, and she fell in love. Carolyn also insisted that they name the kitten Madeline, after the heroic orphan in Ludwig Bemelmans’s childhood classic.
“Carolyn wanted me always to have a companion,” Dana said. “She was so conscious of my situation, that I didn’t have parents. She was able to home in on people and make sure they felt attended to.”
During senior year, Blaine Applegate—who’d remained part of Carolyn’s friend group throughout college—injured his shoulder while playing football. His surgery was scheduled for January, and he would need to stay in the hospital for a few days. “With Carolyn as the ringleader, five girls came with me to the hospital, bringing all kinds of stuff,” he said. “Food, blankets. It was a huge effort for them to gather all of it and come by taxi to the other side of Boston.” The hospital wasn’t in a particularly safe part of the city, “but the girls stayed until they got kicked out. The nurses told them that, ‘For your safety, considering where we are in town, you’d better go now.’ ” Day after day, Carolyn and her crew returned to cheer on Applegate’s recovery.
It was also in her senior year that Carolyn transitioned from waiting tables to being a public relations liaison for That’s Entertainment, a nightclub consortium owned by Patrick Lyons. She promoted two nightclubs on the other side of Fenway Park, 9 Lansdowne and the Metro, by arranging corporate parties for the clubs, chaperoning reporters to the events, and charming them into some good publicity—a piece of cake. If indeed Carolyn studied “being social,” then let it be said she was a quick study.
The summer after senior year, Carolyn and Applegate found themselves both extending the undergraduate four-year plan into a fifth year—with the long hours she was working in PR, Carolyn needed extra time to make up the credits she missed. She moved again, this time to 1030 Commonwealth, where she and Applegate had apartments on the same floor. The building had a rooftop, where Carolyn loved to sunbathe. Applegate worked at Who’s On First, so they kept similar hours: occupied until late at night, with free afternoons.
Applegate lived directly across the hall from the roof access. “Carolyn couldn’t push the heavy lid off to get the door open,” he remembered, “so she’d pound on my door and ask me to open it. I would climb up to get the lid off. She’d go up and sunbathe, and I’d have to put the lid back on after she left.” Sometimes, he would join her. Summer was winding down, and they talked often, squinting at the sky. At times, the conversation got serious.
“Carolyn asked me if I was going to marry my girlfriend, Katie, which was complicated because I had another year of football eligibility, which meant graduate school for me. But Katie wanted me to graduate with her, and I didn’t think I was ready for that.”
“And you and Cully?” Applegate asked Carolyn, referring to John Cullen, whom she was still dating.
“Noooo,” she replied. “I can’t see it. I tell you what: In five years, after we’re out of here and we’ve got nothing going on, let’s find each other and see what happens.”
They fist-bumped on it. Applegate thought of that pact for many years.
Carolyn’s PR job for Lyons eventually became full-time. There, she refined her sense of who, what, and where was hip and current. Her coworker Joe Varange remembers her as “a good schmoozer and networker.
“She was always at ease,” he continued. “She possessed a good mind for business, though business per se didn’t turn her on. She was secure and strong, exceedingly sure of herself. She didn’t take shit from anyone. In other words, it wasn’t possible to intimidate her. She always stood up for herself. If she felt she was being spoken to in a disrespectful manner, she’d say, ‘Excuse me, please don’t talk to me like that.’ ”
One day, Carolyn was getting a ride to work with her friend Denise when Denise’s car, an old beater, wouldn’t start. Denise asked Carolyn to go knock on a nearby friend’s door for help. Alessandro Benetton, heir to the Benetton fashion label, opened the door to see “two watery eyes framed by blonde locks that escaped a wool cap,” Benetton later wrote in his 2022 memoir, La Traiettoria. “Every nuance of her charm captures me at first glance: certain gestures, the way her lips smile.” Carolyn and Alessandro pushed the car while Denise hit the gas. As the car started, Denise called to Carolyn to hurry and get back in before it stalled again, but “she shakes [sic] her head amused, and before walking away, she greets [sic] me with a kiss on the cheek.” However, Alessandro had just accepted a position in the London global finance sector of Goldman Sachs. Like Applegate, he would not forget Carolyn. “In her perfume,” he wrote, “I want to read a promise of the future.”
At the end of the fall semester of 1988, Carolyn had a degree in hand from the Boston University School of Education. That she’d graduated with the same major as her mother must have delighted Ann, who, given the success of her other daughters, already had much to be proud of. Lauren had not only graduated with a degree in economics from Hobart and William Smith Colleges but was also a member of the prestigious Omicron Delta Epsilon honor society. Carolyn marveled at how Lauren had learned Mandarin, a skill that would help her fly up the ranks at Morgan Stanley, where she was hired right after graduation. Lisa, the quietest of the three, had majored in art and was now pursuing her Ph.D. in art history at the University of Michigan. The girls were spreading their wings.
* * *
AFTER GRADUATING, CAROLYN MOVED on her own into a brownstone off Newbury Street, where she lived for a little over a year. Recalled Colleen Curtis in the Daily News, “My memories are of us sitting on the couch, watching General Hospital at three o’clock eating candy bars.”
Though she was good at her job, Carolyn began to ponder her next move. Jonathan Soroff, a reporter for the Improper Bostonian who met Carolyn while he was covering the nightclub scenes she helped create in her role doing PR for Lyons, remembers her as a consummate professional and as much fun as you can be while maintaining that level of competence. “She had to be out at night, or in the late afternoon, showing prospective clients the spaces, hoping they would book it for a party or work event,” Soroff said. “Like any client-services job, you can’t pick and choose your clients. Some were rude and difficult, and plenty of them hit on her. She was overqualified for the job and was not the party girl some later claimed. I never saw her drink more than one glass of wine. She went nowhere near drugs.
“Ostentatiousness of any sort embarrassed her,” he continued, “and she cringed when our transport to an event was a limo. We’d howl with laughter on the way about the gruesome ‘champagne wishes and caviar dreams’ of whoever hired these enormous, fuel-guzzling monstrosities.”
“She would’ve rather been elsewhere,” Dana said. “It was an awful job… That’s why she switched to fashion.”
As for the field of education, when some years later Carolyn was interviewed by Women’s Wear Daily magazine for a 1992 feature on up-and-coming New Yorkers, she explained why she chose fashion over teaching. “At the time, I felt a little underdeveloped myself to be completely responsible for 25 other people’s children,” she said. “And to a large extent, I felt it wouldn’t be provocative enough for me.”
Around her December graduation, Carolyn was getting out of a cab to shop at the Chestnut Hill mall, half an hour away from campus. The store managers of the Calvin Klein boutique in Bloomingdale’s happened to be out on the street, spotted her, and did a double take. She looked a lot like Elaine Irwin, who was a popular model for the brand at the time. They ran after her. Carolyn’s resemblance to Irwin—tall, willowy, and blonde with a patrician profile—got her hired for a sales position on the spot.
Indeed, despite earning her degree in education, Carolyn’s curiosity was still drifting toward fashion. Ann was supportive of Carolyn’s branching out—she supported the choices of all her girls, as long as they worked hard.
It was in these last months in Boston when Carolyn ran into Alessandro Benetton again. He was sitting in a diner when she blew in, grabbing a large coffee before heading to work at the Calvin Klein boutique. Benetton described himself as “mesmerized,” and ran outside to catch up with her. He asked her out for the same evening.
“Why not?” Carolyn replied.
She wanted to go ice-skating, and Alessandro readily agreed. He was a novice on skates, however, and spent the evening “paying the price for my bravado, hanging on Carolyn’s arm in search of balance,” Benetton later wrote. After a first kiss on the wall of the skating rink, they dated for a few months.
They had elegant dinners at the Waldorf Astoria in New York City and went hiking through the woods in New England. Carolyn and Alessandro even went to Boston Bruins games, where Carolyn’s humor was on excellent display.
“Hockey fan to the core, Carolyn—here she is spewing unrepeatable insults, obscene turns of phrase capable of making anyone pale,” Benetton wrote. “The following weekend walking hand in hand with me… before suddenly bursting out with words that sound like poetry, verses that rustle… like autumn leaves.”
Benetton told Vanity Fair Italia, “Carolyn is half of my happiness during my Harvard years… and I think I can say it without betraying her memory, I’m half of hers.” He goes on to say, “Why didn’t it work?… I felt a stimulating affinity and yet we never managed to look further than a weekend.”
Perhaps it was Carolyn looking much further than a weekend—she was looking into her future.
“And the goal was always to go to New York,” Dana Gallo added. “In what capacity, she didn’t know.”
As it happened, New York City came to her. Susan Sokol, then president of the Calvin Klein women’s collection, needed someone for VIP sales, and the New England regional executive quickly put Carolyn’s name forward, saying, “I have the right person for you.”
“Carolyn was perfect for her job at Calvin Klein,” said Jonathan Soroff. “She oozed charisma and looked great. She could have been a highly successful model, but modeling didn’t interest her.”
Within weeks, Carolyn was brought to New York to interview directly with Calvin Klein. According to MJ Bettenhausen, Calvin’s executive assistant at the time who became a close friend of Carolyn’s, the designer was back fresh from rehab and determined to lead a healthy life, but still a little foggy. When Carolyn exited his office, she seemed worried.
“How did it go?” Bettenhausen asked her.
“I don’t know, which is weird. I just can’t tell, so I’m thinking perhaps I bombed,” Carolyn said.
After Carolyn left the office, Calvin called in Bettenhausen.
“We’ve already cast her numerous times, and will again, so why am I meeting with Elaine Irwin?”
Bettenhausen soon called Carolyn back in to meet with the senior vice president, Paul Wilmot, who hired her on the spot.
Job in hand, in the early summer of 1989, Carolyn and another Boston University classmate moved to a tenth-floor apartment at 166 Second Avenue, just a few blocks away from the East Village’s legendary St. Marks Place and Tompkins Square Park. Calvin Klein corporate headquarters was a twenty-minute or so subway commute away, at 205 West 39th Street, the edge of the Garment District, and the epicenter of the New York fashion world of the “Naughty Nineties.”
Carolyn’s “What fun thing will I get to do or see today?” from third grade turned into “What fun thing will I do with my life in this city of endless possibility?” The answer would keep the city itself rapt for the next decade.
CHAPTER FIVE CHAMPAGNE SUPERNOVAS
Spring 1989–Spring 1992
Carolyn represents a time that no longer exists,” observed Michelle Kessler, Carolyn’s colleague at Calvin Klein. There was a sense of liberty and possibility in the worlds of fashion and art in New York in the early 1990s, and that joy encompassed nearly every facet of Carolyn’s life. These were, unbeknownst to the people living through it, the last years of analog, where certain kinds of improvisation and serendipity could be taken as a matter of course. Young people often journey west, or perhaps even to the Far East, to find themselves, but they come to New York to invent themselves. Who should I be? Who are my people? Where is my home? These were the questions animating Carolyn in the first months after her arrival in New York.
