‘Playing chess’
Instead, Carolyn’s approach – ‘prize mindset’ – is being touted as a key factor in capturing John F Kennedy Jr’s attention and interest. On February 22, actor and content creator Serena Kerrigan sparked a conversation on Instagram, sharing that Carolyn (CBK) provides a masterclass in female empowerment – saying she exuded confidence, set boundaries, and didn’t overly invest in the relationship.
In her post, Serena argued that Carolyn was “playing chess” while others were “playing checkers” when it came to landing America’s most eligible bachelor at the time: John F Kennedy Jr aka JFK Jr.
Serena said in the video she posted: “If you are wondering why he’s not obsessed with you, this is your wakeup call… Love Story is a blueprint… she acts cool, calm, and collected because she is the prize.”
The ‘CBK’ rules of engagement
According to Serena’s analysis, Carolyn’s power didn’t come from chasing, but from positioning. Here are the key takeaways Serena highlighted in her post:
◉ The power of ‘no’: When JFK Jr asked for Carolyn’s number, she didn’t give it out. When he offered his, she declined, telling him he knew where to find her at work. This forced JFK Jr to actually put in the physical effort to find her.
◉ Time is a currency: In one standout scene, JFK Jr arrived late to a dinner date only to find Carolyn already walking away. By refusing to wait, she signalled that her time was more valuable than his status.
◉ The ‘vetting’ mindset: During the date, instead of trying to be ‘liked’, Carolyn turned the tables. When JFK Jr asked when it would be his turn to ask questions, she reportedly replied, “I’m the one vetting you, aren’t I?”
◉ Warmth without access: She also pointed out that while Carolyn held firm boundaries, she wasn’t ‘cold’. She was soft, inquisitive, and engaging – but at the end of the night, she kissed him and went home alone, leaving the door open just enough for him to continue the pursuit.
The modern takeaway
According to Serena, Carolyn’s message resonates with today’s generation that is exhausted by the ‘instant access’ culture of dating apps and ghosting. By adopting a ‘prize mindset’, she highlighted that women could stop fawning over ‘high-status’ partners – whether they were celebrities or, as Serena put it, ‘some finance bro’.
She wrote in the caption of her post titled ‘dating advice according to Carolyn Bessette and JFK Jr’: “Be like CBK (Carolyn Bessette-Kennedy) and remember that you are the prize.“
While Love Story takes creative liberties with the couple’s private dialogues, the ‘cool girl’ archetype Carolyn embodied in the 90s remains a cultural touchstone. Whether she was intentionally ‘playing the game’ or simply possessed a high degree of self-worth, the result was the same: one of the most sought-after men in the world was the one doing the chasing.
Carolyn was a US public figure, and wife of John F Kennedy Jr, who was known for her understated fashion sense and elegance. Carolyn and JFK Jr died in a plane crash in 1999 in Massachusetts, US. She was 33.
Note to readers: This report is based on user-generated content from social media. HT.com has not independently verified the claims and does not endorse them.
This article is for informational purposes only and not a substitute for professional advice.
