Jack Schlossberg got serious about his struggle to “find love” in November 2025. But his dating list is nothing to sneeze at.
The grandson of John F. Kennedy Jr. admitted in a New York Times profile that he is “very straight,” despite “people often thinking the opposite.”
The journalist, who is running for Congress, added that he would like to have a wife and children “someday.”
Schlossberg mentioned that she used to use the dedicated dating app Raya, and said, “I dated for a while, but it didn’t really lead to romance.”
The rare comments about his love life come six years after Schlossberg’s love affair with Kendall Jenner made headlines when Kim Kardashian responded to the rumors during an interview with Vogue.
In a 2019 profile, the same reporter quipped, “Mr. Kim’s eyes are shining at the possibility of collusion over dynasty arranged deals.”
Schlossberg hasn’t had any relationships with the reality star since then, but keep scrolling to meet the other women who make up the writer’s dating history.
Kazy David
In July 2018, Schlossberg was reportedly “hanging out” with Kazee David, Larry David’s daughter and Pete Davidson’s ex-girlfriend.
Both had homes on Martha’s Vineyard, according to Radar Online.
“Maybe something will happen, but right now he’s not looking for a relationship,” a source told the magazine at the time.
chrissie jones
Schlossberg was rumored to be dating Chrissy Jones in 2017, but he and Yogi kept their relationship private for two years.
Jones, co-founder of yoga studio Sky Ting, spent Independence Day in 2019 with her family and Schlossberg in Indiana.
Schlossberg posted a selfie with Jones on his Instagram Story at the time, and the two reportedly broke up later that year.
selena gomez
When rumors surfaced in 2024 that Schlossberg was in a relationship with Selena Gomez from 2020 to 2021, she responded with applause.
“I’m sorry, but I’ve never met this human being,” the “Only Bill Murders” star claimed in an Instagram comment.
Schlossberg has never commented on this speculation.
orion carloto
Schlossberg and poet Orion Carloto’s social media activity sparked romance rumors in 2022, and Redditors speculated about it.
Some social media users pointed out that the two were exchanging tweets when Carlo posted via X that “chaos is more comfortable.”
When Schlossberg asked, “More than anything,” she replied, “More than the quietness of life, Jack!!!”
