Jack Schlossberg's Story: History With Taylor Swift, Dated A Yoga Coach, Linked With Selena Gomez

Jack Schlossberg broke the headlines on November 11, 2025, after he officially announced his candidacy for the U.S. House of Representatives in the upcoming 2026 Elections. The young political candidate is contesting New York's 12th Congressional District, a seat currently held by the 78-year-old Democrat, Jerry Nadler, who is stepping down. In the announcement video, Schlossberg made a strong statement, saying he isn't contesting because he has all the answers, but because the people of New York do. The 32-year-old American writer's approach has impressed people, and he has been receiving a lot of love on X and other social media platforms.

Jack Schlossberg launches 2026 US Congress Bid: Inside JFK's grandson's comments on US President, Donald Trump

Even before announcing his candidacy, Jack Schlossberg made headlines by endorsing former US President Joe Biden and Vice President Kamala Harris during their respective campaigns. He even caught everyone's attention when he spoke at the Democratic National Convention. Coming back to his launch speech, Schlossberg has criticised current US President, Donald Trump and even stated that another "Trump term" could trigger a serious "constitutional crisis" in the US. It's fair to say he's not holding back and has shown his determination to bring about change.

One of Jack Schlossberg's biggest strengths is his family history; he is the grandson of one of the most admired and beloved US presidents, John F. Kennedy. Schlossberg has been drawing on his family's political legacy, making multiple promises to the American people, including strengthening civil rights, public service values, and social welfare. It will be interesting to see whether he can bring his grandfather's principles back into practice in the US.

Does Taylor Swift support Jack Schlossberg? Blank Space singer once dated his cousin, Conor Kennedy and here's how Schlossberg reacted to it

Soon after Jack Schlossberg publicly announced his candidacy, people began wondering whether pop icon Taylor Swift would support him. Swift has publicly aligned with Democratic causes, suggesting the possibility of extending support for Schlossberg. However, there's another angle to their dynamics that not everyone is aware of. When Swift was 22, she dated Schlossberg's cousin, Conor Kennedy. Yes! You read it right. She was so much in love with the then-18-year-old Conor that she even penned a song for his parents, Robert F. Kennedy Jr. and Mary Richardson Kennedy.

Taylor Swift and Conor Kennedy dated in the summer of 2012; unfortunately, their relationship ended after just three months. Fast forward to 2025, and Jack Schlossberg was asked whether he was jealous of his cousin, Conor, when he was in a relationship with the pop star, Taylor Swift. The former gave a funny remark as he just said, "Deny". It would be interesting to see whether Swift would extend her support to Schlossberg, as he has criticised her ex, Conor's father, Robert F. Kennedy Jr., in the past, which brought him a lot of trolling on TikTok.

Jack Schlossberg's dating history: Current relationship status, sexuality, dated Yoga instructor Krissy Jones, linked with Selena Gomez and Orion Carloto

Currently, Jack Schlossberg is single and isn't dating anyone. The American author is straight, and he is probably pausing all these things to focus on his political career. However, he has a spicy dating history that is still making a buzz in the gossip columns. Schlossberg fell in love with a Yoga instructor named Krissy Jones in 2017, and they reportedly dated till 2019. Krissy is the co-founder of Yoga Studio and is among the most respected Yoga instructors in NYC. The reason behind their breakup isn't known even to this very day.

After parting ways with Krissy Jones, Jack Schlossberg was linked with iconic singer, Selena Gomez in 2020-21. The link-up stories broke the internet, but Selena denied the rumours, saying, "Never met this human, sorry". After this, Schlossberg reportedly dated famous poet and influencer, Orion Carloto. Although there was no confirmation from them, their dating rumours faded over time. There were also talks that he reportedly spent some time on the famous dating app, Raya, but all this was nothing but internet chatter.

Inside John F. Kennedy's grandson, Jack Schlossberg's educational qualifications: Yale University and Harvard University alumnus, who is a renowned American author

Jack Schlossberg was born on January 19, 1993, to his parents, Edwin Schlossberg and Caroline Kennedy, the daughter of John F. Kennedy. He earned his major in history and political science from Yale University and pursued dual degrees, a JD (law) and an MBA (business), from Harvard University. Not only this, he passed the New York Bar Exam in 2023 and worked as a lawyer and political commentator for some time. Schlossberg is also an author, but not in the traditional sense; he has penned co-eds and numerous articles for publications such as The New York Times, HuffPost, and more.

What are your thoughts on these unknown anecdotes related to Jack Schlossberg's political journey and dating life? Let us know.

Also Read: Nancy Pelosi's Husband Paul Francis: College Couple, 62 Years Of Marriage, DUI Arrest, Hammer Attack

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