Jon Gosselin Has A Scandalous Age Gap Relationship Under His Belt

Jon Gosselin is famous thanks to the very big family he built with his first wife. But Jon's marriage to his now-ex Kate Gosselin isn't the only relationship that put him in the news. In 2009, right when the former "Jon & Kate Plus 8" stars were going through their messy divorce, Jon began a relationship with Hailey Glassman, who joined "The Real Housewives of New York City" in 2026. At the time, Glassman was just 22 and back home from Indiana University, whereas Jon was 32 and, you know, a father of eight.

Because of the timeline of their romance, there was widespread speculation that Jon cheated on Kate. But Glassman denied the rumors, arguing Jon was separated from Kate when the relationship blossomed. The homewrecking narrative was very difficult for her to navigate, especially given her age and naivety. "I want people to know the truth. Right now I'm speaking from my heart, myself. I'm not some celebrity, I'm not some famous person — I'm just a 22-year-old girl who got caught in the middle of all this," she told E! News in August 2009, less than three months after the Gosselins announced their split.

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The relationship didn't last. In December 2009, Glassman broke up with Jon after becoming aware that he had cheated on her with a reporter, news she learned from a deposition amid his contentious divorce. "He became a monster. He's [a] master manipulator and a compulsive liar," she told Radar that month. Nearly two decades later, Glassman still harbors nothing but resentment over her relationship with the former reality TV star. 

Hailey Glassman joined Season 16 of "RHONY" at age 39 in September 2026, 17 years after her relationship with Jon Gosselin. But the time did little to change how she feels about the whole thing. During the season's premiere episode, she revealed details of her relationship that made the age gap even more scandalous. Hailey met Jon because he and Kate Gosselin were friends with her parents. "The reason I dated Jon is because he was my mom's friend, and she was like, 'Oh, he's a great guy!'" she told Erin Lichy (via Bravo).

Jon and Kate became acquainted with the Glassmans thanks to her father, Dr. Lawrence Glassman, a plastic surgeon. "[Kate Gosselin] had six kids at once and wanted a tummy tuck, so my dad did the tummy tuck," Hailey revealed. "And my mom recovered her at the house and stuff, and from there, they became family friends." (Kate has opened up about her procedure with Dr. Glassman before.)

In fact, Jon was living with the Glassmans when he began dating Hailey, something she alluded to back in 2009. "He was living in my house, the person I joked around with. He was sad and bored, I was home and bored," she said in the E! News interview. As brief as the romance was, it left a permanent — and negative — mark on her, largely because she became tabloid fodder. "The media was just destroying me, and at 22 you don't know who you are. That whole ordeal ruined my life," she said in the "RHONY" episode. If it makes her feel any better, Jon's post-reality-TV life hasn't been all sunshine and roses.