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real housewives of new york citySeason 16 Newcomers Haley Glassman Long before she joined the Bravoverse, she had a shocking connection to the reality show.
Glassman, a public relations professional, is one of three new full time cast Join Ronnie In another pseudo-reboot of the Bravo series, following Brene Whitfield, Change Hassan, Raquel Chevremont and Jenna Lyons. glassman’s companion Ronnie Newcomers include celebrity fitness trainers Erica Hammond and makeup artist Daisy Toyplus returning cast members Said Silva, Erin Leach and Jessel Tankalso Carol Radziwill As a “housewife’s friend.”
Glassman first gained notoriety in 2009 when they started dating Jon and Kate Plus 8 Star Jon Gosselin Shortly after breaking up with his wife, Kate Gosselin. The relationship was controversial at the time because Hailey’s father, Dr. Lawrence Glassmanhad previously performed tummy tuck surgery for Kate free of charge.
Hayley’s relationship with Jon was short-lived, and she later made a series Digging him very publiclyincluding mocking the size of his anatomy.
When it comes to love, former reality star Jon Gosselin has definitely been through his share of ups and downs. Jon was married to his ex-wife Kate Gosselin from 1999 until their divorce in 2009, with whom he had eight children. Although the Gosselins’ marriage ended amid accusations of Jon’s infidelity, he (…)
Keep scrolling for a look back at Haley and Jon’s brief relationship.
Haley Glassman’s dad performs tummy tuck for Kate Gosselin
Haley Glassman’s father, plastic surgeon Dr. Lawrence Glassman, brought her into Jon Gosselin’s orbit before they officially started dating. Jon’s ex-wife Kate Gosselin Confirmed Lawrence reached out to her after seeing her on the TLC show complaining about “dog jaw,” or excess skin on her abdomen, due to a C-section surgery.
“A plastic surgeon’s wife happened to see that moment special and she begged her husband to give me a tummy tuck for free,” Kate revealed in a 2025 Facebook video shared by Glassman Plastic Surgery. “She always said, ‘I didn’t need it, so I asked him to give mine to (Kate).'” That’s how it happened. “
She confirmed, “Dr. Glassman did my tummy tuck. (His wife) contacted me somehow through our production company…I literally screamed out loud. I had never even thought about a tummy tuck. I had never even thought it was possible because I knew we couldn’t afford it. The possibilities of it are amazing.”
Controversy over Jon Gosselin and Haley Glassman’s dating schedule
Jon Gosselin and Kate Gosselin announced the end of their marriage on the June 22, 2009 episode. Jon and Kate Plus 8.
“I tried to think about (our marriage) and think about it,” Jon said in the episode. “It’s not good for us to argue in front of our children.”
Later in the episode, he told the camera, “I’m hurt by all this, but I’m excited and hurt because I’m starting a new chapter in my life. I’m only 32 and I really don’t know what to expect.”
Days later it was reported that Jon had entered into a new relationship with Hailey Glassman. August 2009, PR Master Awkward schedule solved Her new relationship with E! News clarified that Jon and Kate had been separated for “a few months” before they started seeing Jon in May 2009.
“Jon and Kate have moved on with their lives — only the audience hasn’t,” she demanded.
Haley Glassman, February 2026.
Photo courtesy of Instagram/Hailey GlassmanIn October 2009, she told insider “Kate wouldn’t call me a homewrecker.”
“I respect (Kate),” Hailey stressed. “She’s like a lioness protecting her cubs. That’s her territory.”
Haley Glassman calls Jon Gosselin her ‘first love’
On her E! News interview, Hailey Glassman said she considered Jon Gosselin her “first love.”
“I’m not a famous person or a celebrity – I’m just a 22-year-old girl who got caught up in all this,” she said. “Give me 15 minutes and you can get it back.”
Jon Gosselin accused of cheating on Haley Glassman
Jon Gosselin is Discover and Star reporter Kate Major in New York in July 2009, but insisted he was just a friend of Major’s.
“My heart will always be with Hailey,” Jon Exclusive story us weekly Same month.
Major contradicted his remarks in an August 2009 interview cbs newsclaiming she was “sad that (Hailey) didn’t know the truth.”
“I don’t have much respect for (Jon),” Major insisted. “I think he handled the situation very poorly. He didn’t act like an adult, a grown man or a father. It’s really sad. I think he’s gotten too carried away with the fame and he’s going on some bachelor romps.”
Hailey publicly sided with Jon at the time, calling the major a “cuckoo” in an interview with E! News in August 2009.
“I know what Jon told me, and I know him,” she insisted.
Hailey Glassman and Jon Gosselin split in October 2009
us weekly report Hailey Glassman and Jon Gosselin split in October 2009 after a whirlwind five-month romance. A few days ago, Glassman told insider She “should not have to endure emotional abuse.”
She told the TV show on October 28, 2009: “We don’t know why we loved him anymore. He would get frustrated and angry and I would be the first to bear the brunt of it. He would call me and take out his anger on me. He had ‘swearing’.”
Later in the interview, she complained: “I cried and said, why are you so mean to me? He took it out on me. He talked down to me and I couldn’t speak. Sometimes he was confused about the truth and he would dance around his lies. He was like Jekyll and Hyde. But I still loved him.”
Jon responds to Hailey’s accusations, telling insider His ex-girlfriend “paid a huge price to live under such a media microscope.”
“I appreciate her emotional support and I regret any pain my actions have caused her as she selflessly endured the stress I endured in the glare of the media,” he continued. “I am committed to getting along well with Hailey, Kate and especially my children. I ask that you give me the opportunity to prove myself.”
Haley Glassman Teases Jon Gosselin’s Anatomy
In February 2010, Hailey Glassman took a photo of her ex-boyfriend Jon Gosselin’s body measurements.
“He was so young I didn’t think he would cheat on me,” she told quit Magazine. “He was hanging like a 9-year-old boy. I’m serious. This is real.”
Hailey claimed that “anyone who sleeps with him will notice” the size, adding, “It’s very noticeable. It’s very small, very small, very small.”
The PR agent recalled that when she once brought up the subject to Jon, he was frustrated.
“He said, ‘You know how deep my subconscious is down there,'” she recalled. “I would tell him to his face, ‘I don’t think you’re going to cheat on me because you’re too young.'” I would tell him that all the time. “
Jon has never publicly responded to Hailey’s insults about his anatomy. Then he married a second wife, Stephanie Lebo2025.
