Glassman: I Paid Jon Gosselin's Child Support

Hailey Glassman, a new cast member on The Real Housewives of New York City, has revealed new details about her past relationship with Jon Gosselin. Speaking on the 'Virtual Reali-Tea' podcast, Glassman stated that her five-month relationship with Gosselin in 2009 actually lasted much longer. She claimed they lived together in New York City while Gosselin was going through his divorce from Kate Gosselin.

Glassman further alleged that she financially supported Gosselin during this difficult period. She stated she "lent" him money and claimed to have paid his child support for a significant duration, noting she was never repaid. Despite these claims, Glassman expressed enduring affection for Gosselin and his current wife, Stephanie, whom she considers family.

Glassman, 39, was only 22 when she began dating the reality star, having met him through her father. Her father had previously performed a tummy tuck for Kate Gosselin. After her relationship with Jon concluded, Glassman married businessman Rubin, while Jon later married Stephanie Gosselin in 2025.

Her re-emergence in the public eye on RHONY has brought her past connection with Jon Gosselin back into focus. Glassman recounted meeting Jon and Kate Gosselin through her family and noted that Jon allegedly stayed at her family's home after separating from Kate, as they were not yet public with their split.

Glassman described how a friendship with Jon evolved into a romantic relationship in May 2009 when she returned home from college. Their relationship quickly became public, leading to negative headlines portraying her as a "homewrecker." She attributed their eventual breakup to the intense media scrutiny and tabloid coverage.

She mentioned that she and Jon did not speak for a couple of years before he reached out with an apology letter. Since then, they have maintained a familial relationship, with Glassman planning to spend Thanksgiving with the Gosselins and expressing fondness for Stephanie.