In November 2025, Jack Schlossberg opened up about his quest to “find love.” His dating history, however, is quite notable.
The grandson of John F. Kennedy Jr. stated in a profile that he identifies as “very straight,” despite others questioning that. He mentioned a longing for a wife and children “someday.”
Even though he keeps his personal life under wraps, he has been linked to several women over the years.
He revealed that he once used the dating app Raya, remarking, “I dated for a spell, but it didn’t really lead to anything.” These rare insights came six years after his brief romance with Kendall Jenner, which caught media attention.
In a 2019 profile, a writer humorously suggested that there might be some “dynasty collusion” regarding Schlossberg and Jenner.
Since then, Schlossberg hasn’t been publicly involved with her, but there are still some notable names in his dating past.
Kazy David
In July 2018, Schlossberg was seen spending time with Kazy David, daughter of comedian Larry David and ex-girlfriend of Pete Davidson. They were reportedly “hanging out” on Martha’s Vineyard.
Sources hinted that while they may have sparked some romance, Jack wasn’t actively seeking a relationship at the time.
Chrissy Jones
Rumors circulated in 2017 regarding Schlossberg’s relationship with Chrissy Jones. They kept a low profile but reportedly celebrated Independence Day together in 2019 in Indiana. A selfie showed the two together, although they eventually parted ways later that year.
Selena Gomez
In 2024, during speculation of a past romance with Selena Gomez from 2020 to 2021, she publicly denied any relationship, stating she had never met Schlossberg, despite the rumors.
Orion Carloto
In 2022, social media interactions between Schlossberg and poet Orion Carloto led to romance rumors. A Reddit user suggested they were linked, noting their exchanges on X, where they seemed to share a playful rapport.
