New 'RHONY' Cast Member Hailey Glassman Faces Backlash Over Past Relationship and Messages

Glassman's connection to Jon Gosselin and alleged messages to influencer Claudia Oshry draw scrutiny ahead of her 'Real Housewives of New York City' debut.

Published on Mar. 5, 2026

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Hailey Glassman, a new cast member on the upcoming 16th season of 'The Real Housewives of New York City', is facing scrutiny over her past relationship with Jon Gosselin and alleged messages she sent to influencer Claudia Oshry. Glassman, a 22-year-old publicist, dated Gosselin in 2009 shortly after his divorce from Kate Gosselin. She has also been accused of sending Oshry a series of critical messages about her appearance and voice since 2017.

Why it matters

Glassman's past relationship with a reality TV star and the allegations of her sending critical messages to another public figure have raised questions about her suitability for the 'Real Housewives' franchise, which is known for its high-profile cast members and dramatic storylines.

The details

Glassman met Gosselin in the mid-2000s when her father, a plastic surgeon, performed a tummy tuck on Gosselin's ex-wife Kate. The two reconnected in 2009 after Gosselin's divorce and began dating, though Glassman claimed there was no crossover with his marriage. Their relationship ended by the end of that year. Separately, influencer Claudia Oshry alleged that Glassman has been sending her critical messages about her appearance and voice since 2017, including comments about her weight and suggestions she undergo cosmetic procedures.

  • Glassman and Gosselin began dating in 2009, shortly after his divorce from Kate Gosselin.
  • Oshry claims Glassman has been sending her critical messages since 2017.

The players

Hailey Glassman

A 22-year-old publicist who is joining the cast of 'The Real Housewives of New York City' for its 16th season.

Jon Gosselin

A reality TV personality who was previously married to Kate Gosselin and dated Hailey Glassman in 2009.

Claudia Oshry

An influencer who has accused Hailey Glassman of sending her critical messages about her appearance and voice since 2017.

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What they’re saying

“I'm not some fame wh**e. 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.”

— Hailey Glassman (E! News)

“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.”

— Hailey Glassman's representative (Daily Mail)

The takeaway

Hailey Glassman's past relationship with Jon Gosselin and the allegations of her sending critical messages to influencer Claudia Oshry have raised concerns about her suitability for the 'Real Housewives' franchise, which is known for its high-profile cast members and dramatic storylines. As she prepares to join the show, Glassman will need to address these issues and demonstrate her commitment to authenticity and respect for all people.