NEWS‘RHONY’ Star Hailey Glassman Says Jon Gosselin Romance 'Ruined' Her Life and Led to 'Lavender Marriage'

Hailey Glassman told 'The Real Housewives of New York City' cast member Jessel Taank that her romance with Jon Gosselin 'ruined my life,' on the Tuesday, September 22, episode.
Sept. 24 2026, Published 7:00 a.m. ET
Hailey Glassman claims her short-lived but highly publicized romance with reality star Jon Gosselin significantly altered the course of her life and laid the groundwork for the "lavender marriage" she's in.
During the Tuesday, September 22, episode of The Real Housewives of New York City on Bravo (via People), Glassman, 39, opened up to cast member Jessel Taank about the impact that the intense media attention surrounding their relationship had on her.
"That whole ordeal ruined my life," Glassman said while discussing the relationship that made her tabloid fodder when she was in her early 20s.
Overwhelming Media Scrutiny

Glassman said tabloids showed up at Indiana University, where she was a student, offering people money for unflattering stories about her.
Glassman said that the negative portrayal she endured as a result of Jon and Kate Gosselin's split caused her significant damage. The media scrutiny was so overwhelming for Hailey that she said it felt like a piece of her died without anyone acknowledging or even mourning the loss.
She also reflected on the extent of the media scrutiny, saying that tabloids showed up at Indiana University, where she was attending school at the time, offering people money in exchange for unflattering stories about her. Ultimately, Hailey said that the constant media attention contributed to the demise of her relationship with Jon.
"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 said. "So it became this whole, like, 'Home-wrecking Hailey, she ruined a family of eight.' That was never the story."
By the time they parted ways, the RHONY star said she felt completely broken down by the attention.
"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."
How Glassman Met Jon

She said her father, a plastic surgeon, performed a tummy tuck for Kate Gosselin after the sextuplets were born, and that she met Jon at 22 while he and Kate were separated.
Hailey's romantic relationship with Jon predates his reality TV fame and developed from connections through her family.
She explained that Kate and her mother were close prior to Jon & Kate Plus 8 airing, and that she got to know Hailey's mom because of her dad's work as a plastic surgeon. After Kate gave birth to her sextuplets, Hailey said, her father performed a tummy tuck for Kate, and her mother assisted Kate during recovery.
As a result of those relationships, the two families eventually became close. Hailey said that she met Jon when she was 22 years old, during a period when Jon and Kate were separated.
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A 'Lavender Marriage'

Glassman described her current marriage to a man she identified only as Rubin as a 'lavender marriage' built on companionship rather than romance.
In addition to sharing information about her previous experiences with Jon, Hailey also discussed her current marriage and referred to it as a "lavender marriage," a type of arrangement based on companionship rather than romance, often between queer partners.
In terms of keeping her husband's identity private, Hailey identified him only as Rubin and said that their arrangement provides her with freedom within defined boundaries.
She expressed that this relationship emerged because of her need for stability following the Jon chapter. Hailey said that if things hadn't unraveled the way they did with Jon, she wouldn't be married to Rubin today, telling producers she chose a life built on safety and self-protection over the one she might otherwise have wanted.
Although Hailey described her arrangement with Rubin as unconventional, she clearly indicated it isn't a polyamorous one, and she said she doesn't date other men.
Moving On

She reconnected with Rubin at Martha's Vineyard after retreating from the breakup.
Hailey revealed that her path to Rubin came at a low point, after she retreated following the breakup. She met up again with Rubin at Martha's Vineyard, and according to Hailey, he encouraged her to reconnect with him at that time.
She said that the timing worked well for her as she was seeking something stable. The couple had a prior bond stemming back to childhood, so their relationship, according to Hailey, was always there.
Hailey has spoken about Jon and his current partner without any hostility and said that the relationship between the two was a sad chapter in her life that she's moved past.
Her history with Jon will now serve as part of her storyline as she joins RHONY for its 16th season.

