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RHONY Newcomer's Shocking Reason for Dating Jon Gosselin
9 Sep
Summary
- Glassman dated Jon Gosselin because her mother wanted her to.
- Her mother's friend Jon Gosselin was introduced to Hailey.
- Hailey's PR career was inspired by her tabloid experience.

Hailey Glassman, a new cast member on The Real Housewives of New York City, has opened up about her controversial 2009 relationship with Jon Gosselin. During the show's season premiere, Glassman disclosed that her mother’s influence was the primary reason she dated Gosselin. She felt a strong sense of responsibility for her mother's happiness and often acted to appease her.
Glassman's father had performed a procedure on Kate Gosselin, leading to Hailey and Jon meeting. Their relationship began after Jon temporarily moved into Glassman's parents' home in May 2009. This highly publicized romance occurred shortly after Jon's separation from Kate. Glassman stated that tabloids wrongly portrayed her as the cause of the Gosselin's marital issues.
She clarified that her relationship with Jon happened months after his separation from Kate. Despite her efforts to manage the public narrative, the aftermath strained her relationship with her mother, who became distant. This period led Glassman to develop a sense of self-reliance. She also noted that this intense media scrutiny inspired her career in public relations, as she sought to help those unable to defend themselves.
Fans will also see Glassman discuss her 15-year marriage to a businessman, whom she met in Martha's Vineyard. She described their relationship as a "lavender marriage." The new season introduces two other Housewives, Erika Hammond and Daisy Toye, alongside returning cast members.