Hailey Glassman has been confirmed as one of the three new cast members set to join the upcoming season 16 of *The Real Housewives of New York City*. Alongside Glassman, the new season will also feature celebrity fitness trainer Erika Hammond and celebrity makeup artist Daisy Toye, while welcome back familiar faces including Erin Lichy, Jessel Taank, and Sai De Silva.
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As a public relations professional, Glassman has established her own agency, aptly named Hailey Glassman PR. With over a decade of experience in the field, she has worked with a diverse array of clients spanning the restaurant, medical, and entertainment industries. Her portfolio includes representation for her father, renowned plastic surgeon Dr. Lawrence Glassman, whose practice, Glassman Plastic Surgery, remains a significant part of her professional life.
Prior to her PR career, Glassman gained public attention due to her relationship with reality TV star Jon Gosselin, famously known for his time on the show *Jon & Kate Plus 8*. Glassman and Gosselin began dating shortly after his divorce from Kate Gosselin in 2009, provoking a media frenzy. At the time, Glassman was just 22 years old and Gosselin was 32. In past interviews, she sought to clarify her role in the public narrative, insisting that their connection began only after his marriage had ended and that she had never aimed to be a “homewrecker.”
The couple’s relationship, which lasted just a few months, ended by the close of 2009. Following their breakup, she appeared on the dating programme *Sweet Home Alabama*, where she expressed her desire to reshape her public image, which she felt had been unfairly tarnished by the media. Glassman asserted that her portrayal as a “fame seeker” was far from reality, stating, “I’ve been constantly judged in rag mags and tabloids. I’m a very kind, sweet, nice girl.”
The announcement of her casting in *The Real Housewives of New York City* has reignited interest in her life and career, coinciding with a heated exchange with influencer Claudia Oshry. Oshry, who operates the popular podcast *The Toast*, accused Glassman of “trolling” her over the years by sending critical private messages about her appearance. In an Instagram video, Oshry revealed screenshots of direct messages sent by Glassman that commented on her weight and voice, describing her as “obsessed” with her physical appearance.
These allegations have drawn considerable media attention, with Glassman being labelled as a “deep internet troll” by Oshry. One particular message, dating back to December 2017, critiqued Oshry’s voice, while others referenced her weight in a way Oshry characterised as intrusive and negative. Glassman’s representative responded to the controversy, asserting that her comments were not intended to “troll” but rather reflect her engagement with Oshry’s content. It was conveyed that Glassman supports body positivity and celebrates women of all shapes and sizes, although she still expressed her opinions about Oshry’s voice.
As production for the new season gets underway, *The Real Housewives of New York City* continues to transform, with the inclusion of new cast members and the return of former ones, signalling a strategic shift in the series’ direction. The show’s original executive producer, Andy Cohen, confirmed that the changes were prompted by a desire to rejuvenate the cast after season 15, which featured several now returning faces alongside newcomers.
Glassman’s addition to the cast not only provides a fresh dynamic for the series, but it also raises curiosity about her past relationships and public image. As the show moves forward, fans and viewers alike are eager to see how her story will unfold within the realm of reality television and the kind of impact she will have on the unfolding drama of New York’s elite social scene.
With filming already commencing, Bravo’s announcement excited fans as they prepare for a new chapter in the *Real Housewives* franchise. With a mix of seasoned stars and fresh perspectives, season 16 promises to deliver the engaging and often dramatic content that viewers have come to expect from this long-running series.