The Real Housewives of New York City newbie Hailey Glassman opened up about the downsides to life in the spotlight while reflecting on her relationship with Jon Gosselin.
During the Tuesday, September 22, episode of the Bravo series, Hailey, 39, recalled the origins of her “unconventional marriage” to husband Rubin. (Hailey noted she goes out with other women, but she insisted the couple aren’t polyamorous.)
“When we got married, there was a lot going on. I was in the tabloids,” she explained, reflecting on her history with Jon, 49. “I just wanted to be safe.”
According to Hailey, Jon “was best friends with my mom before Jon & Kate Plus 8 ever existed.” (The Gosselins’ show originally aired from 2007 to 2009 on TLC before returning as Kate Plus 8.)
“[Kate] had six kids at once and wanted a tummy tuck,” Hailey told costar Jessel Taank. “So my dad did the tummy tuck and my mom recovered her at the house and stuff, and from there, they became family friends.”
Hailey claimed that Jon asked her parents if he could stay with them for a while because he and Kate, 51, were “separated” but “couldn’t tell the public.”
“I come home from college, [it’s] 2009,” she continued. “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.”
Hailey recalled being photographed with Jon while on her dad’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,” she said about the headlines, calling out the “salacious lies” that were allegedly spread about the pair’s relationship.
Hailey and Jon were together for less than six months in 2009. “We broke up because when you’re in the media and you’re in tabloids, it’s awful. And I was just so beaten down,” she admitted.
The new Bravo star shed more light on her past in a confessional, claiming that she felt destroyed by the public’s perception of her connection with Jon.
“At 22, you don’t know who you are,” she said. “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 challenges she faced, Hailey pointed out that the ups and downs led her to finding her husband. She reconnected with the businessman, who she had known “since he was 12,” following her fling with Jon.
“The whole Jon Gosselin situation, if that never happened, my life would be completely different today. … I would have never married Rubin. I would have never chosen a life based on safety and survival,” she told the cameras. “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 was married to Kate, with whom he shares eight children, from 1999 to 2009. He exchanged vows with wife Stephanie in 2025.
The Real Housewives of New York City airs on Bravo Tuesdays at 8 p.m. ET.
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