It’s nice seeing a young Carolyn Bessette in her high school yearbook, pre- John and before all the public attention she received, and being featured in gossip tabloids.

Her classic look, long full bouncy hair, light makeup and very natural.

It’s so lovely to see a young Carolyn Bessette looking genuinely happy, carefree, and at ease.

There’s something incredibly sweet about seeing a young Carolyn Bessette-this happy. The ease in her expression and the light in her eyes make the photo feel so full of life and warmth.

Photo taken by Sasha Chermayeff.

Anecdote shared by R. Couri Hay, publicist and gossip columnist:

“I had the good fortune to see John naked all the time because he was a major exhibitionist.... I want to just preface it by saying I loved him. I respected him. And then I was a major gossip columnist-at one point I had 28 million readers a week at the National Enquirer. It was a professional acquaintanceship. I knew Jackie, I knew Lee Radziwill. So he couldn't avoid me. But John never failed, ever, to smile and say, "Hello, Couri," and it drove everybody crazy when he would do that, because it was like the Camelot seal of approval.

The truth was, he had a love-hate relationship with celebrity, and I think it was more love than hate. He knew he was beautiful. He spent hours and hours at the gym. I never saw him take a shower with the curtain closed. I would see him at the New York Sports Club and then when he was in Aspen at the Aspen Sports Club.

He knew exactly who I was. I'm in the shower across, and John's taking a shower and lathering all up and totally naked and totally comfortable. He could have been a nudist. But the stories-like at a party in Hyannis Port is one of my famous stories I got from a source. Before a big party there, he went skinny-dipping in front of all the gay waitstaff. John was very proud of his body, and I can close my eyes and see every inch of him. The guy was stacked, he had all the right muscles. And there was no shyness about him. He knew I was there. He saw me. He smiled at me.

So in the Aspen Club, he would work out, strip down, no towel, go to the shower. I will tell you that the showers in those days were small. It wasn't pleasant to close yourself in this little shower with a cheap plastic curtain, so it may have been partly convenience. But it was a deliberate move not to close the curtain and one I much appreciated. He was very flirtatious, definitely metrosexual, in touch with all sides of himself. He knew that he was adored and fantasized over.

He used to love to embarrass me. We're in Aspen, at Bonnie's restaurant. He's with all the Kennedys. I go downstairs to go to the bathroom. John Kennedy Jr. walks up to the urinal next to me, whips out his appar-atus, and proceeds to do what men do. I looked at him, he looked at me. I mean, I was so startled. And John looked at me, seeing my embarrassment and everything, and what did he do? He laughed. I think I peed on myself, it was so startling. So he laughed at me, went back upstairs, and then he said, "Let's take a run." And so we went up in the gondola. John had no idea that I could ski. So he picked the most dangerous, the most insane thing. And you know what? I was right behind him. I think he gave me a measure of respect that day. We just had that one run. He went off, I went off, and that was it.”

1991/1992
Gustavo Paredes:
“Carolyn turned him down a few times in the beginning. Given who he was, she didn’t think he was serious. He was flummoxed—challenged. He couldn’t believe she turned him down. He kept figuring out ways to come back to Calvin Klein for business meetings and additional fittings.”

Carole Radziwill in Steve Gillon’s American reluctant prince:
John once told Carole Radziwill that on one of their first dates he scored tickets to a play, but Carolyn got stuck at work and never showed up. (This happened before cell phones and instant messaging.) ‘John was shocked that she stood him up,’ Carole recalled.”

RoseMarie Terenzio:
“The story I heard was that John and Carolyn first met at Calvin Klein. It was around 1991. He had gone to pick out some suits and she helped him—she was the handler for a lot of the VIPs. He asked for her number and they went out on a few dates. Carolyn was dating around and so was John—Daryl was still in the picture, but they seemed to be on and off. Carolyn wasn’t sitting by the phone waiting for his call—it was the opposite. For the first time, he was getting a taste of his own medicine. And that intrigued him.”

MJ Bettenhausen in Once upon a time by Elizabeth Beller:
“In spring 1992, Calvin Klein was just getting back into menswear. None other than John F. Kennedy Jr. had an appointment for a fitting in the VIP room...

John came out of the meeting smitten, with a few men’s suits and Carolyn’s phone number. He called within days.

‘John invited her to join his group at a gala dinner; he was a board member and had purchased an entire table,’ recalled Bettenhausen. ‘Sitting next to him was another woman that Carolyn either mistook as his date, or actually was his date.’ It was unclear, and Carolyn wasn’t pleased. When John invited her to the after-party at a local club, she coldly said, ‘I can’t. I’m meeting people,’ and abruptly left.”

They met again on May 18 at the Don’t Bungle the Jungle II fundraiser, on Pier 25, just off North Moore Street in Tribeca.“

Paul Eckstein in JFK JR an intimate oral biography:
“I remember John at one of our Naked Angels parties coming up and being like, ‘Yo, man, you gotta hook me up. Who is that girl? Introduce me.’ I was like, ‘John, I’m not going to introduce you to anybody. You’re fucking John Kennedy. Go introduce yourself.’ We were doing a 1940s speakeasy theme for this party, and we were both dressed in cheesy 1940s outfits. I had a crush on Carolyn’s sister Lauren. He was trying to get me to help introduce him to Carolyn and I wouldn’t do it. Of course, he met her anyway.”

MJ Bettenhausen in Once upon a time by Elizabeth Beller:
The breakup was messy, especially considering the brevity of the relationship. The week after their summer idyll at Sea Song, Carolyn met John for dinner at El Teddy’s.

Carolyn and John sat in a banquette, where, before they ordered a thing, John presented Carolyn with a letter. The author who sent it to him, a friend of his, came from the milieu of boarding schools, Ivy League universities, and “old money” families of New York, though he didn’t divulge these facts until much later. The letter claimed Carolyn was a user, a partier, that she was out for fame and fortune. And in a grand flourish of the “slut versus the stud” double standard, the epistolatory spy added that Carolyn “dated guys around town.” John casually tossed the piece of paper at her, stood, and walked out the door.

1993/ 1994

Sasha Chermayeff
John had taken me to this event. We were going to dinner, but he’s like, “I’ve got to swing by this place first.” I saw Carolyn from across the room and she was leaning on this post. And I said to myself, That’s the kind of woman that John is so attracted to…. That’s so John’s type right there. We meandered around the party and we’re working our way to the focal point of this party—that woman—and I realize we are not here for any other reason. I remember the way she looked at him and the way he looked at her and I was just like, Okay, this is why I’m here.

He was very casual. We’re just coming to say hi. I didn’t say anything. He was still with Daryl. It was private and I wasn’t going to be like, Oh my God, do you have the hots for her… and what about your relationship? John never said anything to me, but he was overlapping with Carolyn while he was with Daryl—I’m convinced that there was quite a bit of overlap. I think he was obsessed with Carolyn from the minute he met her.

Brian Steel JFK jr an intimate oral Biography:
We were running around Central Park West and we started walking, which was unusual because the guy just wanted to run forever. He said he was completely enchanted by this woman, Carolyn Bessette. And I was like, “What about Daryl?” because they were still together, and he is like, “I think we’re going to break up…. I met her at Calvin Klein.”

He went out on a date or two with Carolyn and he’s like, “I want you to find out as much as you can about Carolyn—I know you know people, like, you know, nightclub people, restaurateurs…. I know you know people that went to college with her.” And so I found out as much as I could about her and not all of it was good. I told him all of it. She was a club girl, and she dated a lot of people.

And then at his birthday party—he used to throw a birthday party at El Teddy’s, the Mexican restaurant in Tribeca—and that year there were about fifteen to twenty friends, and I was sitting directly across from Carolyn, and she had this way of making you feel like you were the only person in the room. She would touch your hands and the hair on the back of my head would go up. She was electric, dynamic. Much more than any photograph could ever capture. Midway through dinner, John pulled me aside and asked what I thought. He was so enthralled, like a kid in a candy shop. I said, “She’s stunning. Enchanting.” And he was like, “That is awesome. I knew you would love her.” Then he said, “I told her everything you told me.” And I said, “You are a moron. Why would you do that?” He was like, “No, no, she loves you.” We did come to love each other.

Rosemarie Terenzio:
She and John had been hanging out on and off—they were both dating other people, but they reconnected in 1994 and it was more serious. They had dinner at Provence downtown, and John gave her the impression he was no longer in a relationship with Daryl and he wanted to date her exclusively. Not long after, there was a picture in the Daily News of John and Daryl holding hands at a movie premiere. Carolyn saw it and cut off contact. Her mom sent her the clipping with a note that said, “Dear Carolyn, please get on with your life. Love, Mom,” with a sad face.

John sent flowers to Carolyn’s office at Calvin and told her it was just this once, that Daryl hadn’t wanted to go to this event by herself, it was something they had planned to go to together, and he felt bad for her. He called several times and left messages, which Carolyn didn’t return—she took her voice off of her answering machine, so there was no message, just a beep.

Once upon a time by Elizabeth Beller:
Less enjoyable was the incessant ring of Carolyn’s phones, both at home and at the office. “John called all the time, but Carolyn was resolute. What we came up with,” says Carolyn’s friend, “was an outgoing message on her answering machine for an imaginary boyfriend.” Anyone who called would get a recording of Carolyn saying, “Hey, hon, I’ll be back by seven o’clock, can’t wait to see you!” The idea was that John would hear it and assume she’d moved on. John did hear it—and he called even more. “Eventually,” says the friend, “Carolyn changed her number.”

Yet some of her friends thought it was an audacious move—a numerical “hard to get”—and that Carolyn still carried hope that she and John would somehow work out in the end.

Rosemarie Terenzio JFK jr an intimate oral biography:
Then the morning after Jackie died, Carolyn saw the news and she called him back. Soon after his mom died, John officially ended the relationship with Daryl, and he and Carolyn got together for good. As they got more serious, I think he was disappointed that Carolyn never got to meet his mom.

Once upon a time by Elizabeth Beller
Despite Carolyn’s steadfastness after John’s mother’s death, their relationship was still touch and go. He was officially with Daryl when Jackie’s life was coming to a close, but his commitment seemed fragile. With the stress and sadness over the loss of his mother, he was at loose ends.

“John was mixing and matching all these women at the same time,” Billy Way said. “I suspect it had something to do with the anxiety he felt over his mother’s suffering.”

Rob Little the men we became
“They began to date secretly at first, I think because they both enjoyed the mystery. Carolyn, a blue-eyed public-school graduate from Greenwich, Connecticut, was working for Calvin Klein…

John first saw her while shopping for suits. He asked someone who she was, got her phone number, and went out on a first date deep in Tribeca…

I met Carolyn for the first time at John’s apartment when they had just begun to get serious. John and I had gone kayaking and I’d stopped in to have a beer before heading home. John didn’t want me to go yet, though. He kept telling me that I should stay another minute because he had a surprise. The minute turned into an hour, but finally the buzzer rang. John became uncharacteristically jumpy.”

Jack Merrill
We had dinner at the Odeon. John had been telling me about Carolyn—This is my new girlfriend and I really like her and she’s gonna come by—and then the chair is empty. He was embarrassed and annoyed. I thought it was hysterical—I loved it from the minute the chair was empty. I just loved the fact that she was an hour late…. Most girls did not do that to John. She showed up and she sat next to me and we laughed from the minute I first looked at her.

Rob Littell, JFK jr an intimate oral biography
She intrigued him more than anyone he’d met. I remember Christina Haag, when she’d broken up with some guy, he goes, “I’m going to marry her.” But Carolyn I think was the most exotic thing he’d ever dealt with in terms of her own capacity, her own passions. She was pretty penigmatic in the sense of who is this wild person—a force of nature.

He said he wanted to marry her. He was adamant. But John and Carolyn—they were just children emotionally on a certain level. They hadn’t had an opportunity to mature. She had her crazy family, too.

Richard Blow, in his book American son

“But we hoped that Carolyn wasn’t stringing John along, because he was ecstatic in her company. When she visited, he could not work. He would gaze upon her as if he couldn’t completely believe what his eyes were taking in. He could not stop touching her, running his fingers through her hair, stroking her arms. Carolyn accepted his attentions but rarely reciprocated. At least in public, John was the more openly affectionate of the two.”

Do you think Carolyn was playing hard to get, or was it just her personality to be late, take her time to respond, etc.? Even when they were already together, many mention he was the most affectionate.

What do you think about the letter? Many versions talk about it, so it must have some truth to it. But Brian Steel, who investigated Carolyn, said he saw her soon after telling John everything, and he was surprised they hadn’t broken up. Carole also confirmed this story recently on the Deuxmoi podcast.

Excerpt from American Son, Richard Blow

“If most people revered celebrity, John romanticized the ordinary, and Carolyn's everyday background was part of what attracted him to her. Her roots not only would give her the strength to be John's partner, but they would also help him stay grounded. Carolyn provided John a link to the lives of average Americans. At the same time, she was beautiful, passionate, and vivacious. She didn't seem to be at all intimidated by him. People said John was like Jay Gatsby, and though that analogy had some merit-both men had seamless, seductive exteriors-there was an essential difference between the two. Gatsby knew who he wanted to be but denied who he was; John knew who he was, but not who he wanted to be. If anyone was Gatsbyesque, it was Carolyn. She was the social dreamer intent upon self-transformation. But as she herself would admit, behind her carefully constructed beauty there swirled a maelstrom of insecurity. Was she pretty enough for John? Strong enough? Did he really love her?

She wasn't book smart; Carolyn didn't read many books-but she compensated with ambition. At college she posed for "The Girls of B.U." calendar, which later embarrassed her. The calendar was testimony to how much work had gone into her current appearance. In her photo Carolyn looked girl-next-door sweet— big-eyed, big-haired, a bit Madonna circa 1985, nothing like the sleek fashion icon she would become. She seemed softer, more accessible than the woman who, in her need to protect herself, had adopted a hard shell.

From the time she started being photographed with John, she felt pressure to look the part of his physical peer. But unlike John, Carolyn had to work for her looks. She subjected herself to injections of Botox, a bacteria that numbed the nerves in her forehead, so that she would not frown and develop wrinkles. She dieted herself rail thin, plucked her eyebrows until they were mere wisps, dyed her hair the color of white corn. She was sitting in my office once when John walked in and began stroking her hair. "Not so hard, okay, baby?" Carolyn said, squirming a little. "I've got so many chemicals in this hair; you're going to break it." She was half-joking, but only half. 

I wished that the public could have seen John and Carolyn at their happiest, as they were just weeks later when they hosted a George party in Washington. Held on March 25, 1996, at the luxurious home of socialites Peggy and Conrad Cafritz, it was an intimate gathering of perhaps sixty people, including George Stephanopoulos, Secretary of Commerce Ron Brown, and Health and Human Services Secretary Donna Shalala. Chic, for Washington.

About an hour into the evening, after a cool spring night had descended, I saw John and Carolyn standing by a window near the bar. Someone was making a toast in the living room and the other guests had gravitated that way. With a mischievous smile, John slid the window open and dropped to the patio a few feet below.  Carolyn slipped off her heels and followed, grasping the windowsill as John held out his arms and eased her to the ground, then reached for her hand. As they walked slowly through the moonlight, they stopped to kiss, Carolyn lifting her lips to John's. They didn't return until the party was winding down, and when they did, smiles danced around their faces like little waves lapping at the edges of a pool.”

- In her college years Carolyn was praised for being “most beautiful person”, Richard mentions that Carolyn thought it was so cringe and was embarrassed by it and insecure. Will we ever know who she really was? Some just glorify the “most beautiful person” part, but seldom do we hear that she was embarrassed by it.

 

- Why do you think Carolyn wanted so desperately to look different, different from what she looked at Calvin Klein?  Why didn’t she leave her hair as is, the person who John fell in love with? Carolyn was not only changing her exterior, but she was also changing from within.

- Why did she change her hair to this “white corn” color as Richard says, and why did she get rail thin? Billy Noonan, John’s friend later shared that Carolyn was obsessed with Jackie. Did she try to be as rail thin as Jackie?  

- Why was she slowly transforming herself to look very polished, almost perfect (in her mind).

- Do you think she really subjected herself to Botox? 

See pictures for transformation. 

(Disclaimer if my English is bad or if my grammar doesn't sound good. English is not my first language.)
I personally think she wasn't the it girl of the nineties. I personally think models were an example, such as Kate Moss. Since Heroin chic was very in at that time. 90s minimalism was very in if I'm correct. So I personally think she was following trends. I don't think she was a trendsetter. Unless we are talking about her wedding dress. If you had to ask me about the young people today like myself and how we view her in a fashion sense. I probably say she is becoming the face for the Wasp Girl image. I personally see that style among the types of people. I think the 90s minimalism was a rebellion from the 80s bright colors. I honestly think it was a bore reminds me of office work. I personally think she really didn't bring anything new to the table when it came to fashion or how we view it. I personally think Carolyn is becoming a bit oversaturated since everyone is copying her style I feel like it's losing the mystique. I personally hate the style, it was a bore to me at first but the mystique she had. It drew me in. God, she had some aura. I hope everyone has a great day!