The dynamic between John and his sister, Caroline, had always been such that he was reluctant to disagree with her. Going all the way back to when they were children, he never wanted to fight with his only sibling. Jackie had raised them to work out any differences. Usually, though, John just let Caroline have her way. It was easier. He wanted to keep the peace with the one person in the world who meant the most to him, and anytime something came up that had the potential to be a problem between them, he would decide it wasn’t worth it and shy away from taking a stance.
When it came to his love life, though, things became a little more complex for John. Caroline never approved of any of the women in his life, with the possible exception of the actress Christina Haag, who John had dated for a few years before Daryl Hannah and who’d also had the approval of Jackie. Because Caroline’s knee-jerk reaction was to just be contrary about John’s women, he had come to the conclusion—as did others—that she’d simply never be happy with anyone he chose. In her eyes no one would ever be good enough for him. Unlike other disagreements, where John would acquiesce, when it came to this subject he would listen and then just do what he wanted to do. Caroline would be vexed and her disapproval would fester between them for the duration of the relationship, but she was never able to actually make him end it with any woman.
True to form, Caroline Kennedy didn’t approve of Carolyn Bessette. The first time anyone knew for sure there was a problem was back in 1994 at a holiday meal at Caroline and Ed’s home. It was a festive occasion hosted by the Schlossbergs with John and Carolyn and Anthony and Carole in attendance. After dinner, they all clinked glasses and talked about their New Year’s resolutions. Anthony vowed to stay out of the hospital. “Good luck with that,” John said, ribbing him, as always. “And I think Carolyn’s resolution should be to just marry John once and for all,” Carole piped in, smiling at her friend.
“I don’t think so…” said Ed Schlossberg.
“Oh? And why is that, Ed?” Carole asked, biting back a smile. She thought he was joking. He wasn’t. “Because Caroline doesn’t even know her,” Ed said with a stern face.
Carolyn and Caroline just looked at each other in chilly silence. At that point, to hear Carole tell it years later, one could hear a pin drop. After a few awkward moments, everyone tried to recover and go on with dinner. However, it was clear that trouble was on the horizon.
When Carolyn later questioned John about the awkward moment, she felt let down by his response. He actually seemed fine with his sister not getting to know her. “She’s not going to like you, so why bother?” he asked. This made no sense to Carolyn. One relative in whom she confided recalled, “She said, ‘That’s not how people in the real world are with each other,’ to which John responded, ‘Welcome to the Kennedys’ world, where it’s either sink or swim. My sister is the last one who’s going to throw you a life raft.’ Carolyn persisted. ‘But I need to get to know her,’ she told John. ‘Maybe lunch or something?’ No, John said. ‘Just leave it alone, Carolyn.’ The more she pushed, the more John resisted. ‘Jesus, I said leave it alone, will you please?’ he finally exploded. Then he left the room, annoyed. She told me she was upset about it and wondered what it all meant.”
In the months to come, it became obvious that Caroline would never be close to Carolyn. They were just different kinds of women. Style and fashion meant a lot to Carolyn, for instance, and not much to Caroline. Caroline interpreted Carolyn’s interest in clothing as a sign of her superficiality. Also, Carolyn was forthcoming and open as a person, whereas Caroline was much more subdued and harder to know. There were many other differences, but they were mere personality quirks. In short, Carolyn simply rubbed Caroline the wrong way. The truth was that John’s fiancée wasn’t her cup of tea. Though it bothered John, he knew better than to make an issue of it.
The highly public fight in the park, though, really illustrated why Caroline was so critical of Carolyn. She actually blamed her for it. She felt she’d been with John long enough to know what sorts of things pushed his buttons, and that she should’ve known to avoid those triggers while in public. “Get to know my brother,” is how she put it. She was used to her cousins dragging the family name through the mud, but not John. She then had words with him about the melee along the lines of: “How do you think Mummy would like it?” He felt bad enough already; Caroline just made him feel a lot worse.
Caroline was now clear that John shouldn’t marry Carolyn—at least not anytime in the near future. She felt that the fact that they’d been screaming in each other’s faces was evidence enough that they weren’t a good match. Certainly, she and Ed would never have had a fight like that. They were different people, though. They were so mild-mannered with each other, at least from all outward appearances, some people in their lives couldn’t help but feel that maybe an explosive airing of feelings once in a while might actually do them a world of good.
The siblings debated John’s engagement to Carolyn until there was nothing left to say about it. Finally, John felt the only way to smooth things over was to ask Carolyn if she would have Caroline be her matron of honor. However, Carolyn had two sisters with whom she got along well, so why would she want John’s disapproving sibling to fill that role? The only reason, maybe, was because John had asked her. After some deliberation, she agreed.
What could Caroline say? Declining Carolyn’s request would just cause more problems. Therefore, she agreed to accept the honor. The two then made a real effort to at least act as if they got along for John’s sake. However, to say they were close during this time would definitely be overstating things.