Jack Schlossberg, the 31-year-old grandson of John F. Kennedy, is publicly navigating the aftermath of a breakup, using social media to express his feelings and process the situation. Schlossberg, who is the son of Caroline Kennedy and Edwin Schlossberg, recently posted a series of reflective messages and videos on TikTok and Instagram, providing fans with a glimpse into his emotional state as he deals with the end of a relationship.
On Sunday, Dec. 1, Schlossberg shared a shirtless mirror selfie on Instagram, posing in light gray sweatpants and a beanie. The post, which featured a series of images including a selfie at the Metropolitan Museum of Art and a vanity license plate, was accompanied by a caption quoting the Nicene Creed, a Christian prayer. Schlossberg added a personal touch, writing, “IT IS SILLY. BUT I BELIEVE” at the top of the post.
The Instagram post, which some followers might have interpreted as a “thirst trap,” comes after Schlossberg posted several videos on TikTok earlier in the week that seemed to hint at a difficult breakup. In one TikTok shared on Thanksgiving Day, Nov. 28, Schlossberg reflected on the emotional turmoil of ending a relationship, offering a raw insight into his feelings.
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“Someone said this to me the other day — you feel like you’re mourning someone who’s alive,” Schlossberg said in the video. His words, which resonated with many viewers, highlighted the strange and painful experience of grieving a relationship that isn’t truly “lost” in the conventional sense. He went on to explain the difficult mindset that often accompanies breakups. “You can’t get so down about breakups because — that’s the thing — the other person’s a psychopath. If they didn’t want to be with you, they’re so dumb,” he added with a mix of humor and frustration.
Schlossberg’s candid words about heartbreak appeared to reflect advice passed down from his father, Edwin Schlossberg, who married Caroline Kennedy, the only surviving child of President John F. Kennedy and Jacqueline Kennedy Onassis. According to Jack, his father has always maintained that breakups are “always mutual,” suggesting that if a relationship is no longer working, it’s best to “be happy” and “move on.”
Schlossberg continued to share his emotional journey on social media when, on Nov. 30, he posted another TikTok video. This time, he sang an a cappella rendition of “What Kinda Gone” by country artist Chris Cagle, while walking through the streets of New York City just before dark. In the caption, Schlossberg wrote, “I’m going thru a tough breakup. This Chris Cagle song is helping.” The video, featuring his soulful performance, resonated with fans who have faced similar heartache.
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@jack.schlossberg Breakups are always mutual — my dad’s maxim — Going tbrough it rn guys !
The public sharing of his emotions marks a rare glimpse into the life of Schlossberg, who has largely stayed out of the spotlight despite his prominent family connections. As the only grandson of JFK, Schlossberg has occasionally made headlines, but he has mostly kept his personal life private. His mother, Caroline Kennedy, is the U.S. Ambassador to Australia, while his father, Edwin, is an artist and designer. Schlossberg himself has focused on his education, graduating from Harvard University, and has expressed interest in pursuing a career in law and public service, following in the footsteps of his legendary grandfather.
While Schlossberg’s posts may seem like an unconventional way to process a breakup, they offer an honest look into his emotions and the impact of his personal experiences. His willingness to share his vulnerability online has resonated with many followers, who have expressed their support in the comments. In the age of social media, where celebrities often curate their public personas, Schlossberg’s openness about his struggles stands out as a rare and refreshing moment of authenticity.
Despite the emotional weight of the breakup, Schlossberg’s recent posts hint at his resilience and determination to move forward. His posts, from the philosophical Nicene Creed to the heartfelt TikTok performances, suggest that he’s grappling with his feelings while also finding moments of clarity and humor.
