Jack Schlossberg, the grandson of President John F. Kennedy, recently opened up about his struggles to find love and detailed his past relationships in a candid November 2025 interview, offering a rare glimpse into the personal life of the political scion amid his congressional campaign. This revelation humanizes the often-private figure, highlighting the universal challenges of dating even for those in the public eye.
In a New York Times profile, Schlossberg confirmed he is “very straight” and expressed his desire to have a wife and children “one day,” directly addressing rumors about his sexuality. He shared that he used the exclusive dating app Raya, going on dates that ultimately did not lead to love, underscoring the difficulties of forming meaningful connections in the modern dating landscape. These comments mark a departure from his usual privacy, as he navigates increased scrutiny due to his political ambitions.
Schlossberg’s dating history includes several notable relationships and rumors. He was romantically linked to Krissy Jones, co-founder of the yoga studio Sky Ting, from 2017 to 2019. The couple spent time together, including a Fourth of July celebration in 2019, which Schlossberg commemorated with a social media post before their relationship ended later that year. This period represented one of his more publicized romances, though he typically kept details under wraps.
Earlier, in 2018, he was rumored to be involved with Cazzie David, daughter of comedian Larry David, with sources indicating they were “hanging out” in Martha’s Vineyard but not pursuing a serious relationship. Additionally, speculation arose in 2024 about a past connection with singer Selena Gomez, but Gomez swiftly denied ever meeting him, calling the claims baseless in a social media response. These instances illustrate how his associations often spark public interest, regardless of their accuracy.
In 2022, social media exchanges with poet Orion Carloto fueled romance rumors on platforms like Reddit, though neither Schlossberg nor Carloto addressed the speculation. His interactions, such as responding to her tweet about comfort in chaos, led fans to theorize about a potential relationship, but it remained unconfirmed. This pattern of online speculation highlights the challenges of maintaining privacy in the digital age, especially for someone with a prominent family name.
The context of Schlossberg’s life as a Kennedy heir and congressional candidate adds layers to his dating narrative. Born into a political dynasty, he has faced constant public curiosity about his personal affairs, which he has largely managed to keep separate from his professional endeavors. His decision to discuss love and relationships now may stem from a desire to connect authentically with voters, showing that he shares common human experiences despite his privileged background.
Schlossberg’s openness could have implications for his public image and political career. By revealing his dating struggles and aspirations, he demonstrates vulnerability that might resonate with constituents, fostering a sense of relatability. This approach aligns with broader trends where public figures use personal stories to build trust and authenticity, potentially strengthening his campaign as he seeks to represent New York’s 12th Congressional District.
As Schlossberg moves forward, his candid remarks on love and dating may continue to shape perceptions of him as a modern, approachable leader. Whether this transparency will influence his political success remains to be seen, but it undoubtedly adds depth to his story, reminding audiences that behind the headlines, individuals seek fulfillment in relationships just like anyone else.
