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Hailey Glassman says she quietly covered a large chunk of Jon Gosselin’s child support during his contentious split from Kate Gosselin — and she still hasn’t been repaid. The Real Housewives of New York City star spoke about the loan in a recent interview, revisiting a chapter of her life that ties her to one of reality TV’s most famous families.
How a private loan became public gossip
Glassman told reporters she stepped in to help Jon financially during his divorce from Kate. The claim echoes earlier reporting that placed the amount at a substantial sum.
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- Reported loan amount: A 2010 Radar Online story put the figure at $88,000.
- When it happened: The loan was said to have been made in October 2009.
- Hailey’s comment: She says she never received repayment but remains on friendly terms.
Why the loan drew attention
The high dollar figure and the timing — during one of reality TV’s most scrutinized divorces — magnified interest. Jon and Kate’s family was a national story then. Any personal connection to Jon invited headlines.
From introductions to romance: the early ties between Glassman and Gosselin
Their relationship began through family connections. Hailey’s father, Lawrence Glassman, known as a plastic surgeon, had treated Kate. That put the families in the same social circle.
- Hailey and Jon met when she was young and he was an established TV figure.
- Their romantic relationship reportedly began in mid-2009.
- They lived together in New York City for a period.
Media pressure and the breakup
Glassman says the intense coverage of Jon’s divorce complicated their life together. They separated later that year. Still, she describes their relationship as longer and more involved than the headlines implied. Jon later reached out to apologize for how things unfolded, she added.
Where both moved next: marriages and public life
Both have moved on publicly. Glassman is in a so-called “lavender marriage” with businessman Rubin Cronig. Jon remarried in 2025 to Stephanie Lebo.
Career notes and TV connections
Jon left the family’s series after the divorce, which continued under Kate’s name. Hailey has since entered the Bravo universe with Real Housewives of New York City. Viewers can catch new RHONY episodes on Tuesday nights at 8 p.m. ET on Bravo, with episodes streaming on Peacock the next day.
Custody fight and the Collin Gosselin story
The family’s custody disputes have remained a topic of intense public interest. Control of the children shifted over time, and Collin Gosselin’s situation drew intense scrutiny.
Key developments in custody
- After the divorce, Kate initially had custody of the children.
- Jon later received sole custody of his son Collin in 2018 after Kate did not appear at a hearing.
- At times, Collin and his sister Hannah were reported to be living with Jon.
Collin’s placement in a behavioral facility raised major questions. He and Jon have said Kate placed him in a facility without Jon’s prior knowledge nearly two years earlier. The reasons given by each side differ sharply.
Allegations and denial
- Collin has publicly said he believes he was institutionalized because he no longer wanted to film the family show.
- Kate Gosselin has denied those claims and attributed the placement to concerns about Collin’s behavior.
- Collin is preparing a memoir titled “In the Shadow of Eight,” where he plans to discuss his experience.
What Hailey says about family ties now
Despite the drama, Glassman describes an ongoing, familial connection with the Gosselins. She plans to spend holidays with members of that extended circle and insists the relationship endured beyond the brief public romance.
Notable timeline
- 2006: Hailey’s father reportedly performed Kate’s cosmetic procedure, linking the families.
- June 2009: Hailey and Jon reportedly started dating as his separation from Kate became public.
- October 2009: The couple is said to have split; the alleged loan also dates to this period.
- 2018: Jon wins sole custody of Collin after Kate misses a hearing.
- 2025: Jon marries Stephanie Lebo.
Public reaction and the lasting headlines
Stories about the Gosselin family have followed them for years. Loans, custody rulings, and personal statements continue to surface, keeping the family in the tabloids and on social feeds. Hailey Glassman’s recent remarks add another chapter.
Why this still matters
- The case touches on child welfare and parental rights.
- It illustrates how reality TV blurs private life and public curiosity.
- High-profile loans and custody battles create long-lasting press cycles.
