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If you purchase an independently reviewed product or service through a link on our website, SheKnows may receive an affiliate commission. It's hard to believe that Carolyn Bessette never had the opportunity to meet her future mother-in-law, Jackie Kennedy, before her death on May 19, 1994. John F. Kennedy Jr. had his reasons for keeping the two women apart, but it was something he regretted when he went on to marry Bessette in 1996. More from SheKnows JFK Jr. Was Reportedly Rattled by the Death of Princess Diana for This Carolyn Bessette Reason JFK Jr.'s decision to not have Jackie meet his future wife is chronicled in an upcoming book about Bessette's legacy: Once Upon A Time: The Captivating Life of Carolyn Bessette-Kennedy by Elizabeth Beller. The first issue for one of America's most eligible bachelors was his dating life — it was messy. He was casually seeing Bessette, but his timeline with Kill Bill star Daryl Hannah also showed that in 1994, they were still dating. Bessette perhaps thought that meeting the former first lady might seal her fate as JFK Jr.'s one and only girlfriend as it was not a secret that Jackie didn't want her son to marry an actress. Carolyn Bessette Kennedy. "Carolyn became increasingly irked that he wouldn't introduce her to his mother," Beller wrote, via an excerpt obtained by People. "'I took him to meet my mom,' Carolyn told a friend." The author elaborated further on the hot topic with the media outlet, noting that JFK Jr. was also launching his magazine, George, at the time, which became his core focus. "I think it was hard for him to take anything other than his work too seriously at that moment," she explained. "If Carolyn met Jackie, I think he knew that that would sort of become a life of its own. And maybe he wasn't quite ready for that." It was a pretty big sticking point in their relationship and their on-again, off-again status "was sometimes off because [Bessette-Kennedy] would break up with him over the fact that he wasn't introducing her to Jackie." Bessette stood her ground because she "wasn't going to put up with anything like that." The truth is that Jackie probably would have loved Bessette, who was vastly different from Hannah and her Hollywood lifestyle as a Calvin Klein public relations executive. Singer Carly Simon also explored JFK Jr.'s mom's distaste for Hannah in her 2019 memoir, Touched by the Sun: My Friendship With Jackie. "Jackie was very consumed with getting him on the right path," she wrote, and "didn't approve" of the actress. The former first lady even went so far as to move to another room to eat her meal if the Splash star came over for dinner. In the end, it was a major missed opportunity for JFK Jr. to introduce Jackie to a woman, who probably checked off every box on his mom's list. Bessette and Jackie would have loved each other. Before you go, click here to see photos of JFK and Jackie O.'s grown-up grandkids. John Schlossberg, Caroline Kennedy, Tatiana Schlossberg Best of SheKnows 42 Celebrities Who've Had the Most Dramatic Hair Transformations 22 Women That Movies & TV Tried to Tell Us Were Fat 39 Royals Who Married Commoners Over the Years Sign up for SheKnows' Newsletter. For the latest news, follow us on Facebook, Twitter, and Instagram.