Say What? 'RHONY' Newbie Hailey Glassman Dated Jon Gosselin for a Short Time

As anticipation for Season 16 of The Real Housewives of New York City grows, fans are trying to learn everything they can about the cast. While we already know that former franchise stars are returning, fans have been intrigued by the new faces. With a former WWE wrestler and celebrity makeup artists in the mix, it’s sure to stage the stage for a new dynamic. However, folks have also been busy diving into the life of newbie Hailey Glassman.

Hailey, a public relations professional, is the third newbie rounding out the cast. While some folks may know her as the daughter of plastic surgeon Dr. Lawrence Glassman, she’s ready to show the world and Bravo fans who she is as a person. However, one of the most intriguing things about Hailey is who she was once connected to. Word on the street is that she used to date Jon Gosselin. Is it true? Here’s everything that we know.

Hailey apparently dated Jon when she was in her twenties.

Per People, Hailey met Jon and the Gosselin bunch while her dad performed a tummy tuck on Kate Gosselin in the mid-2000s. Jon and Kate announced their split in 2009. That May, Hailey and Jon became a thing.

It’s typically a dating faux pas to entertain or enter a relationship with a man fresh out of a divorce. However, Hailey was smitten with Jon at the time. In an interview with E! News, per TV Guide, she explained that their friends-to-romance transition began when Jon stayed at her parents' house after his separation. Keep in mind, Hailey was 10 years Jon’s junior at the time.

"I'm not some fame w---e," she says. "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."

That said, when you enter an already messy situation, it’s only a matter of time before the other shoe drops. Many folks never banked on Hailey and Jon’s relationship to go the distance, and by the end of 2009, both parties went their separate ways.

RHONY is nowhere close to airing Season 16, but the drama has already started. Influencer Claudia Oshry, aka @girlwithnojob on TikTok, has called out Hailey for being a troll.

In a March 3, 2026, TikTok video, Claudia starts off by showing a Deux Moi post about the Season 16 RHONY cast. While she says she is familiar with a few of the names, once she saw Hailey’s name, she knew that she was familiar with her as well.

Claudia goes on to share that after looking at her Instagram in hopes of recollecting the connection, she went to her DMs and realized that Hailey was a “deep internet troll of [hers] in 2017.”

In the first screenshot, you see a message from Hailey to Claudia that reads: “OMG, your voice is so annoying like Janice from Friends.”

In another, Hailey says, “Damn, you were thin,” and “Skinny minnie,” in another DM. Claudia claims that she must have posted an old photo of herself and says that Hailey is “obsessed with [her] weight.”

She then posts another receipt of Hailey sending her a message about being on weight loss drugs.

“Looks great, but you gotta own you’re on Wegovy,” the message reads. “You’re an influencer, and you really should be honest on your platform about it. When you need any skin tightening since you definitely lost enough to need it, I’ll set you up with a great plastic surgeon in NYC."

She then messaged her again, offering her the opportunity to “take care of [her] skin” from the weight loss. The DMs continued, with Hailey commenting on Claudia’s partner and congratulating her on her pregnancy.

Once the news made its rounds, it didn’t take long for Hailey’s team to respond.

“Hailey’s responses were in no way trolling, she was simply engaging with Claudia’s provocative content,' Hailey’s rep told The Daily Mail. “Ms. Glassman is the daughter of a very respected and prominent plastic surgeon who offered her plastic surgery advice to an outspoken influencer who posts nonstop about her weight.”

The rep continued by accusing Claudia of playing the victim and said that Hailey respects everyone.

"Let’s face it, bullying Ms. Glassman all while playing the victim, after openly having to apologize for her own past bullying, is a bad look. She should be embarrassed," the rep said.

"Ms. Glassman is in support of all people. She has expressed that women are beautiful, in every shape, every size. They’re all sexy, but she says the sexiest of all is authenticity and respect to all groups of people."

The rep also took a moment to be petty and say that Hailey "stands by her statements about Claudia’s voice."

Will this issue be shown in the forthcoming Season 16? Only time will tell.