REALITY TV NEWSRHONY's Hailey Glassman Claims She Once 'Paid' Jon Gosselin's 'Child Support' Bill During Kate Divorce
Hailey Glassman claims ex Jon Gosselin owes her money for child support.
Oct. 2 2026, Updated 8:03 a.m. ET
Hailey Glassman is still waiting for her ex Jon Gosselin to reimburse her.
“I paid his child support for a very long time during that divorce,” Glassman said in a new interview. “Never got paid back, but it’s OK, Jon! I know you’re working through it. I love you forever.”
Gosselin has eight children with his ex-wife Kate Gosselin, whom he married in 1999. The former couple filed for divorce in 2009.
How Much Does Jon Gosselin Allegedly Owe Hailey Glassman?
Hailey Glassman reportedly loaned Jon Gosselin $88,000 for child support.
Hailey loaned Jon $88,000 in October 2009, according to a 2010 report. He allegedly could not afford to pay Kate, so Hailey gave him a check to help him out.
“This was back when Kate was accusing Jon of emptying their bank account. A judge ordered Jon to pay her back the money, and he didn’t have it, so Hailey loaned him the money,” a source close to Hailey told the publication.
Has Jon Gosselin Responded to Hailey Glassman’s Allegations?
Jon Gosselin has not spoken out about owing Hailey Glassman money.
At this time, Jon has not verified Hailey’s claims. While he has not said whether he actually owes Hailey money, this is not the first time he has faced accusations involving finances. In 2009, Kate accused Jon of taking $230,000 from their joint bank account and leaving her with just $1,000, according to the report.
How Long Were Hailey Glassman and Jon Gosselin Together?
- ‘RHONY’ Star Hailey Glassman Says Jon Gosselin Romance 'Ruined' Her Life and Led to 'Lavender Marriage'
- 'RHONY' Newbie Hailey Glassman Says Her Mom Pushed Her to Date Jon Gosselin: 'He's a Great Guy'
- 'She Still Won't Let It Go': Jon Gosselin Slams Estranged Ex-Wife Kate for 'Dragging Him Back to Court' With $132K Child Support Appeal
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Hailey Glassman dated Jon Gosselin for about five months.
The Real Housewives of New York City star and Jon dated for about four to five months, beginning their relationship in June 2009 before calling it quits that October. Hailey was 22 at the time, while Jon, who had recently separated from Kate, was 32. Their romance was frequently in the spotlight, which ultimately put a strain on the relationship and contributed to their breakup.
Who Is Hailey Glassman Dating Now?
Hailey Glassman is married to a businessman named Rubin.
Hailey is married to a businessman named Rubin, who has chosen to keep his last name private. The Martha’s Vineyard native and the reality star have an unconventional relationship, which Hailey has openly discussed.
"I'm in a lavender marriage," Hailey said in an interview published September 7. "We've known each other since he was 12 years old. We were neighbors in Martha's Vineyard, and we met at sailing camp."
They’ve been married since 2011.
Who Is Jon Gosselin Dating Now?
Jon Gosselin married Stephanie Lebo.
Jon married his long-time girlfriend, Stephanie Lebo, in November 2025. Stephanie is a cosmetologist and a chemist and has one daughter named Juliana.
