Hailey Glassman Says She Paid Jon Gosselin's Child Support Amid Divorce

Hailey Glassman, a new cast member of "The Real Housewives of New York City," has revealed that she financially supported her former partner, Jon Gosselin, by paying his child support during his highly publicized divorce from Kate Gosselin. Glassman stated in an interview with Page Six's "Virtual Reali-Tea" that she provided this financial assistance for an extended period and has not yet been reimbursed.

Glassman shared that she paid his child support "for a very long time during that divorce," adding, "Never got paid back, but it’s OK, Jon! I know you’re working through it. I love you forever."

According to a June 2010 Radar Online report, Glassman allegedly loaned Gosselin $88,000 in October 2009. Glassman met Gosselin through her parents; her father, plastic surgeon Lawrence Glassman, performed Kate Gosselin's tummy tuck procedure in 2006. Glassman, then 22, began dating Gosselin, then 32, in June 2009, the same month he and Kate announced their separation on their TLC show.

Although media reports indicated their split in October 2009, Glassman stated they dated longer and lived together in New York City. She attributed their eventual breakup to the intense media scrutiny surrounding their relationship. Gosselin reportedly reached out years later to apologize, and Glassman stated they have remained close, even attending Thanksgiving together.

Glassman is now in a "lavender marriage" with businessman Rubin Cronig. Jon Gosselin married Stephanie Lebo in 2025.

Following his divorce from Kate, Jon Gosselin left their television show, which was later retitled "Kate Plus 8." Kate Gosselin was initially granted full custody of their eight children. In 2018, Jon Gosselin was awarded sole custody of their son, Collin Gosselin, after Kate failed to appear at a custody hearing. Their daughter, Hannah Gosselin, also resided with him at that time.

Collin Gosselin has since spoken out about his experiences, including his time in a behavioral facility he claims his mother placed him in without Jon's knowledge. He is preparing to release a memoir titled "In the Shadow of Eight."

Kate Gosselin has denied her son's accusations.