Hailey Glassman has been spilling the tea about her life, including her past relationship with Jon Gosselin, since joining The Real Housewives of New York City — and she’s just getting started.
The new Housewife, 39, revealed during the Tuesday, September 29, episode of Page Six’s “Virtual Reali-Tea” podcast that she dated Gosselin, 49, “a lot longer” than the reported five months in 2009.
Hailey claimed that the pair “lived together in New York City” and she “lent” him money amid his divorce from Kate Gosselin.
“I paid his child support for a very long time during that divorce,” she alleged. “Never got paid back.”
Hailey, who is still friends with Jon, was quick to point out there were no hard feelings about the alleged loan.
“But it’s OK, Jon. I know you’re working through it. I love you forever, family,” she added, looking directly at the camera.
Us has reached out to Jon’s rep for comment.
Hailey gained notoriety in 2009 when she began dating the Jon & Kate Plus 8 star following his split from Kate, 51, to whom he was married for 10 years. (The exes share twin daughters Mady and Cara, 25, and sextuplets, Alexis, Hannah, Aaden, Collin, Leah and Joel, 22.)
Jon Gosselin and his girlfriend Hailey Glassman arrive at the Oak Room by carriage on October 17, 2009 in New York City. Arnaldo Magnani/Getty Images
Hailey was only 22 years old when she was romantically involved with the reality star, having met Jon through her father, Dr. Lawrence Glassman. (Dr. Glassman performed Kate’s tummy tuck for free when Hailey was just a teenager.)
Following her split from Jon, Hailey went on to marry businessman Rubin, who opted not to be on RHONY. Jon, for his part, married Stephanie Gosselin in 2025.
Hailey’s connection to Jon has been thrust back into the spotlight following her debut on season 16 of RHONY.
During the September 22 episode, Hailey detailed how she met Jon and Kate, noting that after Kate’s tummy tuck, her mom helped with the recovery process and they “became family friends” with both Kate and Jon.
Jon Gosselin and Hailey Glassman are proving that exes can still be pals. “Such a great night with my husband @jongosselin1 supporting our girly @haileyglassman1 at her first @bravotv Real Housewives of New York premiere! 🍎✨🥂,” Jon’s wife, Stephanie Gosselin, wrote via Instagram on Wednesday, September 9, alongside a photo with Glassman, 39, and other […]
Once Jon and Kate separated, he allegedly asked Hailey’s mom if he could stay at their family home because they “couldn’t tell the public” about the breakup just yet.
Hailey was away at college at the time, but when she came home for the summer in May 2009, Jon was living with her parents.
“I was 22, and at that point, they were already separated and not together. But the public didn’t know. So a friendship turned into more,” she told costar Jessel Taank. “And then it was on TMZ and they were like, ‘Jon with mystery woman.’ … So it became, like, this whole, ‘Homewrecking Hailey, she ruined a family of eight,’ and that was never the story.”
When it comes to love, former reality star Jon Gosselin has certainly experienced his share of ups and downs. Jon was married to ex-wife Kate Gosselin, with whom he shares eight children, from 1999 until the pair’s divorce in 2009. Though the Gosselins’ marriage came to an end amid accusations Jon had ben unfaithful, he […]
Hailey called the headlines “salacious lies” that prompted their split.
“We broke up because when you’re in the media and you’re in tabloids, it’s awful. And I was just so beaten down,” she confessed.
Hailey explained on Tuesday that she and Jon didn’t speak for a couple of years before he reached out “apologizing” for everything.
“He wrote me a letter apologizing. Then we met up. We just were family ever since,” she told podcast listeners. “I’m going to them for Thanksgiving. I love Steph, his wife, is wonderful.”
