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Live the Gossip > Lifestyle > “RHONY”’s Hailey Glassman Explains Why Jon Gosselin Romance ‘Ruined’ Her Life and Led to Her ‘Lavender Marriage’ with Mystery Man
Lifestyle

“RHONY”’s Hailey Glassman Explains Why Jon Gosselin Romance ‘Ruined’ Her Life and Led to Her ‘Lavender Marriage’ with Mystery Man

Written by: News Room Last updated: September 22, 2026
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“If that never happened, my life would be completely different today,” Hailey says during the Sept. 22 episode of ‘The Real Housewives of New York City’

Credit: Jason Howard/Bauer-Griffin/GC Images

NEED TO KNOW

  • Real Housewives of New York City newcomer Hailey Glassman gets candid about how her previous relationship with Jon Gosselin led to her current “lavender marriage”
  • “If that never happened, my life would be completely different today,” Hailey says during the Tuesday, Sept. 22 episode of RHONY 
  • New episodes of RHONY air Tuesdays at 8 p.m. ET on Bravo

Real Housewives of New York City newcomer Hailey Glassman is getting candid about her past relationship with Jon Gosselin.

Hailey’s marital arrangement has been a hot topic among the RHONY cast ever since she revealed she is in a “lavender marriage.” In a preview clip from the Tuesday, Sept. 22 episode of RHONY shared by Bravo, Jessel Taank, 46, questioned the rules of Hailey’s marriage to her husband, whom she referred to as Rubin. 

“Do you guys operate like a married couple?” Jessel asked. 

“We have an unconventional marriage where he lets me do my thing,” Hailey replied. “Just no other guys. Like, I don’t date other men. But it’s not, like, some poly [situation]. … Nothing like that.” 

Hailey Glassman and Erika Hammond on ‘The Real Housewives of New York City’Credit: Ralph Bavaro/Bravo
Hailey Glassman and Erika Hammond on ‘The Real Housewives of New York City’
Credit: Ralph Bavaro/Bravo

Hailey noted that she and Rubin have known each other since they were 12, and that she was going through “a lot” when they got married. “I was in the tabloids,” she said. “I just wanted to be safe.”

When Jessel asked her why she made headlines, Hailey opened up about her past relationship with the former Jon & Kate Plus 8 reality star. 

Jon came into Hailey’s life when her father performed a “tummy tuck” on Kate Gosselin after she gave birth to their sextuplets, and from there, Hailey said, Jon and her mom became “family friends.” When Jon and Kate separated, Jon moved into her parents’ house. Hailey noted that happened around the time she came home from college, and the two developed a close friendship that turned romantic.

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Hailey explained that her relationship with Jon became a scandal because he and Kate hadn’t publicly announced their separation yet. 

“We were on my dad’s yacht, and someone got a photo of us, and then it was on TMZ, and they were like, ‘Jon with mystery woman, and plastic surgeon’s daughter,’” Hailey recalled. “So it became this whole, like, ‘Home-wrecking Hailey, she ruined a family of eight.’”

“That was never the story,” she added, saying the tabloids at the time “only care about salacious lies.”

Hailey Glassman; Jon GosselinCredit: Jason Howard/Bauer-Griffin/GC Images; Tommaso Boddi/Getty
Hailey Glassman; Jon Gosselin
Credit: Jason Howard/Bauer-Griffin/GC Images; Tommaso Boddi/Getty

In her confessional, Hailey explained that the media’s portrayal of her relationship with the reality star deeply affected her. 

“The media was just destroying me, and 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.”

Hailey told Jessel that, at the time, tabloids “invaded” Indiana University, the school she attended, and asked people to give them a “juicy story” on her in exchange for $100. The media and their narrative are why Hailey and Jon broke up, she said. 

She said, “I was just so beaten down.” 

After she and Jon broke up, Hailey ran into Rubin at Martha’s Vineyard and they reconnected. 

“The whole Jon Gosselin situation — if that never happened, my life would be completely different today. And when I say that, [I mean] I would have never married Rubin,” she said in her confessional. “I would have never chose 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, and I needed to protect myself and my soul.” 

New episodes of The Real Housewives of New York City air Tuesdays at 8 p.m. ET on Bravo and stream the next day on Peacock.

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