The Real Housewives of New York City’s season 16 newbie Hailey Glassman had an outrageous connection to reality TV long before she joined the Bravoverse.
PR pro Glassman is one of three new fulltime cast members joining RHONY in another pseudo-reboot of the Bravo series, following the departures from Brynn Whitfield, Ubah Hassan, Racquel Chevremont and Jenna Lyons. Glassman’s fellow RHONY newcomers include celebrity fitness trainer Erika Hammond and makeup artist Daisy Toye, plus returning cast members Sai De Silva, Erin Lichy and Jessel Taank, as well as Carole Radziwill as a “friend of the Housewives.”
Glassman first gained notoriety in 2009 when she started dating Jon & Kate Plus 8 star Jon Gosselin shortly after his split from wife, Kate Gosselin. The relationship was controversial at the time because Hailey’s father, Dr. Lawrence Glassman, had previously performed Kate’s tummy tuck for free.
Hailey and Jon’s relationship was short-lived and she later made a series of very public digs about him, including mocking the size of his anatomy.
Jon Gosselin’s Dating History: Marriage, Scandal and More
Keep scrolling for a look back at Hailey and Jon’s brief relationship.
Hailey Glassman’s Father Performed Kate Gosselin’s Tummy Tuck
Hailey 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, has confirmed that Lawrence reached out to her after seeing her complain on her TLC show about having the “jowls of a dog,” or excess skin on her midsection, due to her C-section procedures.
“A plastic surgeon’s wife happened to see that hour special and she begged her husband to do my tummy tuck for free,” Kate revealed in a 2025 Facebook video shared by Glassman Plastic Surgery. “She always said, ‘I didn’t need one so I asked him to give mine to [Kate].’ That’s what happened.”
She confirmed, “Dr. Glassman did my tummy tuck. [His wife] contacted me through our production company somehow … I literally screamed at the top of my lungs. I never even thought about a tummy tuck. I never even thought it was possible because I knew we couldn’t afford it. The possibility of it was amazing.”
Controversy Over Jon Gosselin and Hailey Glassman’s Dating Timeline
Jon and Kate Gosselin announced that they were ending their marriage during a June 22, 2009, episode of Jon & Kate Plus 8.
“I tried to contemplate [our marriage] and think about it,” Jon said during the episode. “It’s just not good… for us to be arguing in front of our kids.”
Later in the episode, he told the cameras, “I’m hurt by all of this, but I’m excited and hurt at the same time because I have a new chapter in my life. I’m only 32-years-old and I really don’t know what’s going to happen.”
There were reports days later that Jon had already started a new relationship with Hailey Glassman. In August 2009, the PR guru addressed the awkward timeline of her new relationship with E! News by clarifying that Jon and Kate were separated for “months” before she started seeing him in May 2009.
“Jon and Kate have moved on with their lives — it’s only the viewers who haven’t moved on,” she demanded.
In October 2009, she told The Insider that “Kate wouldn’t say I was a home wrecker.”
“I have respect for [Kate],” Hailey stressed. “She’s like a lioness protecting her cubs. That’s her turf.”
Hailey Glassman Called Jon Gosselin Her ‘First Love’
In her E! News interview, Hailey Glassman said that she considered Jon Gosselin to be her “first love.”
“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 said. “Take my 15 minutes, you can have it back.”
Jon Gosselin Was Accused of Cheating on Hailey Glassman
Jon Gosselin was spotted with Star reporter Kate Major in New York City in July 2009 but he insisted that he was only friends with Major.
“My heart is always with Hailey,” Jon exclusively told Us Weekly that same month.
Major disputed his comments during an August 2009 interview with CBS News, claiming that she felt “badly for [Hailey] that she doesn’t know the truth.”
“I don’t have a lot of respect for [Jon],” Major insisted. “I think he handled the situation very poorly. He did not act like an adult or a grown man or a father. And it’s just sad. I think the fame has just gone to his head and he’s on some bachelor romp.”
Hailey publicly took Jon’s side at the time, calling Major “cuckoo” during an interview with E! News in August 2009.
“I know what Jon tells me and I know him,” she insisted.
Hailey Glassman and Jon Gosselin Split in October 2009
Us Weekly reported in October 2009 that Hailey Glassman and Jon Gosselin had split after a whirlwind five-month romance. Days earlier, Glassman had told The Insider that she “shouldn’t have to put up with being emotionally abused.”
“We’re at a point now where I don’t know why I love him,” she told the TV show on October 28, 2009. “He gets frustrated and angry and I’m the one who gets the brunt. He’ll call me and take his anger out on me. He has ‘mantrums.’”
Later in the interview, she complained, “I cry and say why are you so mean to me? He takes it out on me. He talks over me so I can’t speak. Sometimes he has trouble with the truth and he will dance and dance around his lies. He’s like Jekyll and Hyde. But I still love him.”
Kate and Jon Gosselin’s Rocky History: Alleged Affair, Custody Battles
Jon responded to Hailey’s allegations by telling The Insider that his ex-girlfriend “paid a significant price to live under such a media microscope.”
“I am grateful for her emotional support and I regret any pain that my actions have caused her as she has selflessly born the pressures I have endured under the media glare,” he went on. “I am committed to making things right with Hailey as well as Kate and especially my children. I ask you to please give me the opportunity to prove myself.”
Hailey Glassman Mocked Jon Gosselin’s Anatomy
In February 2010, Hailey Glassman took a shot at the size of her ex-boyfriend Jon Gosselin’s anatomy.
“He was so small I didn’t think he would cheat on me,” she told Steppin Out magazine. “He’s hung like a 9-year-old boy. I’m serious. This is true.”
Hailey alleged that “anybody who sleeps with him will notice” the size, adding, “It’s very noticeable. It’s so tiny, tiny, tiny.”
The PR agent recalled Jon getting upset when she broached the subject matter with him once.
“He said, ‘You know how subconscious [SIC] I am of down there,’” she remembered. “I would tell him to his face, ‘I don’t think you would cheat on me because you’re so small.’ I would tell him that all the time.”
Jon never publicly responded to Hailey’s insults about his anatomy. He subsequently married his second wife, Stephanie Lebo, in 2025.
