Hailey Glassman is still waiting for Jon Gosselin to pay back her hefty child support loan.
The “Real Housewives of New York City” newbie exclusively revealed to Page Six’s “Virtual Reali-Tea” that she financially supported the “Jon & Kate Plus 8” alum amid his highly publicized divorce from Kate Gosselin.
“I paid his child support for a very long time during that divorce,” Hailey, 39, told us. “Never got paid back, but it’s OK, Jon! I know you’re working through it. I love you forever.”
According to a June 2010 Radar Online report, Hailey allegedly loaned Jon a whopping $88,000 in October 2009.
Hailey was a teenager when she met Jon through her parents, who became family friends with the Gosselins after her father, plastic surgeon Lawrence Glassman, performed Kate’s tummy tuck in 2006.
At the encouragement of her mother, Hailey, then 22, and Jon, then 32, began dating in June 2009 — the same month he and Kate announced their separation on their TLC show, which followed their lives with twins and sextuplets.
While she and Jon, now 49, reportedly split up in October 2009, Hailey told us they dated “a lot longer” than most people think, explaining that they “lived together” in New York City.
They ultimately split up because of the heightened media attention surrounding their relationship, though Hailey said Jon reached out a couple of years later “apologizing” for the way things turned out.
“We’re family ever since,” she said. “I’m going to them for Thanksgiving.”
Hailey is now in a “lavender marriage” with businessman Rubin Cronig, while Jon married Stephanie Lebo in 2025.
Following his divorce from Kate, Jon left the family’s television show, which rebranded to “Kate Plus 8,” and his ex-wife was granted full custody of their eight children.
In 2018, Jon was granted sole custody of their son, Collin Gosselin, after Kate failed to attend the custody hearing. Their daughter, Hannah Gosselin, was also living with him.
At the time, Collin was living in a behavioral facility that Kate had allegedly placed him in without Jon’s knowledge nearly two years earlier. Collin has said he believes his mother had him institutionalized because he no longer wanted to film the family’s show, though she claims it was due to his “unpredictable behavior and violent tendencies towards” family members.
Collin has since been outspoken about the alleged abuse he faced from his mother, and is preparing to share his story in his upcoming memoir, “In the Shadow of Eight.”
Kate, for her part, has vehemently denied her son’s accusations.
“The Real Housewives of New York City” airs Tuesday nights at 8 p.m. ET on Bravo, with new episodes available to stream the next day on Peacock.
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