Who Is ‘RHONY’ Newbie Hailey Glassman? Her History With Jon Gosselin & More

The Real Housewives of New York City is returning for a 16th season and will feature a handful of new cast members. One of the new ladies is Hailey Glassman, who will join returning members Erin Lichy, Jessel Taank, and Sai De Silva, as well as fellow newbies Erika Hammond and Daisy Toye.

It’s been more than a year since Season 15 of RHONY concluded in February 2025, and while there were initially rumors that the show was being canceled, Andy Cohen confirmed that the casting process was underway in May 2025. Bravo announced the official cast on March 2.

Glassman previously made headlines for her relationship with Jon Gosselin. Scroll down for a refresh on that and to learn more about her.

What happened between Hailey Glassman and Jon Gosselin?

Glassman dated Gosselin in 2009 after his split from Kate Gosselin. She was introduced to the former couple in the mid-2000s when her father, a plastic surgeon, performed Kate’s tummy tuck.

Glassman and Gosselin reconnected when he moved to New York City after the divorce and temporarily stayed with her parents. At the time, he was 32 and she was 10 years his junior. “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 an interview with E!, per TV Guide.

The pair’s relationship began a month before Gosselin and his ex-wife announced their divorce, but Glassman insisted there was no crossover and claimed Jon and Kate were separated for “months” before she started dating him.

“I’m not some fame wh**e,” Glassman said. “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.” The two split by the end of 2009.

What does Hailey Glassman do for a living?

Glassman, who splits her time between New York and Martha’s Vineyard, is a publicist who owns the company Hailey Glassman PR.

“As a public relations professional with over 10 years of experience in the industry, I’ve had the pleasure of working with leading clients in the restaurant, medical and entertainment industries,” her website says. “We go above and beyond to help your brand most effectively portray your unique identity and build compelling relationships with your audiences.”

Is Hailey Glassman in a relationship now?

While Glassman’s current relationship status is not confirmed, she appears to be single.

What happened with Hailey Glassman and Claudia Oshry?

After Glassman’s casting on RHONY was announced, she was called out by influencer Claudia Oshry on social media. Oshry posted a TikTok with screenshots of messages that Glassman had been sending her since 2017.

The first alleged message was sent on December 20, 2017, and said, “Omg your voice is so annoying. Like Janice from Friends.” In 2020, another message was sent that said, “Damn, you were thin,” and Oshry claimed, “She’s obsessed with my weight.”

@girlwithnojobNot to make everything about me….♬ original sound – Claudia Oshry

She then pointed to another DM that read, “Looks great but you gotta own you’re on Wegovy. You’re an influencer and you really should be honest on your platform about it. When you need any skin tightening since you def lost enough to need it, I’ll set you up with great plastic surgeon in NYC.”

There was another message that said, “Incredible shrinking woman. Once you get to where you want, we’ll take care of you for a 30s neck lift.” As recently as June 11, there was a message that said, “So weird how you were skinnier pregnant than you were 2 years ago not pregnant. You’re a magician!”

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After the video went viral, Glassman’s rep told Daily Mail, “Hailey’s responses were in no way ‘trolling,’ she was simply engaging with Claudia’s provocative content. Ms. Glassman is in support of all people. She has expressed women are beautiful, every shape, every size. They’re all sexy but she says the sexiest of all is authenticity and respect to all groups of people. With that said Hailey stands by her comment regarding her distaste for Claudia’s voice.”

The Real Housewives of New York City, Season 16, TBA, Bravo