All the Kennedy bachelor’s girlfriends, flings
Jack Schlossberg got real about his struggles to “find love” in November 2025 — but his dating roster isn’t anything to sneeze at.
John F. Kennedy Jr.’s grandson confirmed in a New York Times profile that he is “very straight” despite “people often wonder[ing]” the opposite.
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The journalist, who is running for Congress, added that he hopes to have a wife and kids “one day.”
Schlossberg mentioned that he previously used the exclusive dating app Raya, noting, “I went on dates for a while and they didn’t really lead me to find love.”
The rare comments about his love life came six years after Schlossberg’s crush on Kendall Jenner made headlines after Kim Kardashian reacted to the rumor during a Vogue interview.
“Kim’s eyes twinkle at the prospect of colluding over some dynastic matchmaking,” the reporter quipped in the 2019 profile.
While Schlossberg and the reality star have not been linked since, keep scrolling to meet the other women making up the writer’s dating history.
Cazzie David
Schlossberg was reportedly “hanging out” with Larry David’s daughter — and Pete Davidson’s ex-girlfriend — Cazzie David in July 2018.
The duo both had Martha’s Vineyard homes, according to Radar Online.
“Maybe it could be something, but right now he’s not looking for a relationship,” a source told the outlet at the time.
Krissy Jones
Schlossberg was rumored to be dating Krissy Jones in 2017, but he and the yogi did not publicly reveal their romance for two years.
Jones, the co-founder of yoga studio Sky Ting, spent the Fourth of July with her family — and Schlossberg — in Indiana in 2019.
Schlossberg posted a selfie with Jones via Instagram Stories at the time, and the duo reportedly ended things later that same year.
Selena Gomez
When rumors surfaced in 2024 that Schlossberg had been linked to Selena Gomez between 2020 and 2021, she clapped back.
“Never met this human sorry,” the “Only Murders in the Building” star claimed in an Instagram comment.
Schlossberg, for his part, never commented on the speculation.
Orion Carloto
Schlossberg and poet Orion Carloto’s social media activity led to romance rumors in 2022, which Redditors speculated about.
Some social media users pointed to the duo exchanging tweets when Carloto wrote via X that she was “more comfortable in chaos.”
When Schlossberg asked, “Than in what,” she replied, “than in the stillness of life, jack!!!”
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