Everything We Know About JFK's Grandson Jack Schlossberg's Dating History

Even though he's already a Kennedy and bears a striking resemblance to his uncle John F. Kennedy Jr., Jack Schlossberg has become something of an internet celebrity thanks to his quirky online presence. Still, much of Schlossberg's personal life remains shrouded in mystery. However, tidbits of information on his dating life have leaked out. For instance, in 2018 he was rumored to be spending time with actor and writer Cazzie David, the daughter of actor and comedian Larry David. A source confirmed to Radar Online that Schlossberg and Cazzie were casually seeing each other. "They just started hanging out for the summer because they both have places on the Vineyard," they clarified. "Jack is going to Harvard for his second year of law school come September." 

The insider made it clear that it wasn't an exclusive relationship, adding, "Jack's just hanging out with different people." Although they didn't rule out it turning into something more, "right now he's not looking for a relationship." A user on X, formerly known as Twitter, shared a screenshot of Schlossberg commenting on one of Cazzie's Instagram posts, quipping, "Jack Schlossberg making jokes about wine on Cazzie David's Instagram revived me like a shot of espresso." However, not much else is known about their relationship, which was never officially confirmed.

Another reported relationship of Jack Schlossberg's was with Krissy Jones, a yoga studio owner. They reportedly dated sometime in 2017 but seemed to rekindle their relationship in 2019, according to a source who spoke to Radar Online. Supposedly, Schlossberg even skipped that year's family trip to Hyannis Port, Massachusetts — one of the late Jackie Kennedy's favorite summer destinations, which the extended Kennedy family usually visits for the July 4th holiday — to spend time with Jones and her family in Indiana.

However, things ended between Schlossberg and Jones sometime that same year, with the insider divulging, "[Jones] told friends that it's over between them. She said he snuck around on her." They continued, "She said it's for the best." The cheating rumors were never confirmed. Otherwise, not much is known about Schlossberg's relationships. However, the identity of his rumored celebrity crush was revealed in a 2019 interview with a big-name reality star. 

During a 2019 Kim Kardashian interview and photoshoot with Vogue, Jack Schlossberg's reported crush on her younger sister, Kendall Jenner, was brought up. Kardashian was described as looking interested in such a match, according to the writer. After the article was published, an insider disclosed to Hollywood Life that momager Kris Jenner was also excited about the idea and wanted to set Kendall and Schlossberg up. In fact, according to the source, "Kris is hoping that the crush turns into a relationship, love and more!" 

Kendall looks just as beautiful in real life as she does on Instagram, but it seems that a romance between her and Schlossberg never happened (as far as we know, at least). JFK's grandson kept mum about whether he was single or not in his own July 2024 interview with Vogue, telling the outlet simply: "no comment." That is likely not going to stop his fans from wondering about it though, especially considering Schlossberg is one of the most gorgeous Kennedy grandchildren.