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Hailey Glassman Says Jon Gosselin Romance “Ruined My Life”

Sep 23, 2026 By Ashley B What do you think?

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Hailey Glassman Jon Gosselin

Real Housewives of New York City newbie Hailey Glassman is opening up about the lasting impact of her highly publicized relationship with Jon Gosselin.

During the September 22nd episode of RHONY, Hailey reflected on how her relationship with Jon, 49, shaped the life she ultimately chose.

“When we got married, a lot was going on. I was in the tabloids,” Hailey explained. “I just wanted to be safe.”

Hailey said Jon had been friends with her family long before Jon & Kate Plus 8 premiered on TLC in 2007. According to Hailey, Jon was “best friends with my mom” before the Gosselins became reality TV stars.

“[Kate] had six kids at once and wanted a tummy tuck,” Hailey told RHONY costar Jessel Taank. “So my dad did the tummy tuck, and my mom recovered her at the house and stuff. From there, they became family friends.”

Hailey claimed Jon eventually asked her parents if he could stay with them because he and Kate were “separated,” but allegedly couldn’t tell the public.

“I come home from college, [it’s] 2009,” she recalled. “I was 22, and at that point, they were already separated and not together. But the public didn’t know. So a friendship turned into more.”

That relationship quickly became tabloid fodder after Hailey and Jon were photographed together on her father’s boat. “And then it was on TMZ and they were like, ‘Jon with mystery woman.’ So it became, like, this whole, ‘Homewrecking Hailey, she ruined a family of eight,’ and that was never the story.”

Hailey said the media attention took a major toll on her. “We broke up because when you’re in the media, and you’re in tabloids, it’s awful. I was just so beaten down. At 22, you don’t know who you are. It’s almost like, if you could rewind your life in time and pinpoint that one moment where a piece of you died, but there was no funeral for you.”

“That whole ordeal ruined my life.” Despite the painful experience, Hailey said the relationship ultimately changed the trajectory of her life. She later reconnected with Rubin, a businessman she had known since he was 12.

“The whole Jon Gosselin situation, if that never happened, my life would be completely different today.” Hailey continued, “I would have never married Rubin and I would have never chosen a life based on safety and survival.”

“I didn’t choose a life that I wanted for myself; I chose a life to be safe. I needed to protect myself and my soul.”

Jon and Kate were married from 1999 to 2009 and share eight children.

Real Housewives of New York City airs on Bravo Tuesdays at 8 p.m. ET.

Do you remember the ‘Homewrecking Hailey’ headlines? Pop off below.

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Bravo TV Real Housewives TLC Bravo Bravo TV Buzz Hailey Glassman Jon & Kate Plus 8 Jon Gosselin Real Housewives of New York City RHONY TLC

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