Hailey Glassman, the former girlfriend of Jon Gosselin, has returned to television as a cast member of The Real Housewives of New York City Season 16. The public relations professional has attracted attention for discussing her unconventional marriage, her relationship history, and the media controversy that followed her romance with Gosselin in 2009. Her appearance on the Bravo reality series has also renewed interest in Hailey Glassman’s age, career, husband, and personal background.
At 39 years old, Glassman is introducing herself to a new generation of reality television viewers. Although she first became recognizable through celebrity headlines nearly two decades ago, she has since established a public relations business and built a life with her husband, Rubin Cronig.
How Old Is Hailey Glassman?
Hailey Glassman was born in February 1987, making her 39 years old as of November 2026. She was approximately 22 when her relationship with Jon Gosselin became public in 2009.
Her age attracted considerable attention during that relationship because Gosselin, who was born on April 1, 1977, was 32 at the time. Their roughly ten-year age difference became a frequent subject of entertainment coverage.
Now, Glassman is returning to television with a different perspective. Her appearance on RHONY allows viewers to learn about her professional accomplishments, marriage, and experiences beyond the relationship that originally made her famous.
Who Is Hailey Glassman?
Hailey Glassman is an American publicist, entrepreneur, and reality television personality. She grew up in a family connected to the medical profession and later attended Indiana University.
Her father, Dr. Lawrence Glassman, is a plastic surgeon who performed an abdominal procedure for Kate Gosselin. This professional connection brought the Glassman and Gosselin families together before Hailey began dating Jon.
Glassman eventually pursued a career in public relations, establishing her company, Hailey Glassman PR. Her business has worked across industries including entertainment, hospitality, and healthcare.
She has explained that her early experiences with tabloid attention influenced her decision to enter publicity. Having experienced intense media coverage herself, she developed an interest in helping others manage their public image.
Hailey Glassman Joins The Real Housewives of New York City
Hailey Glassman joined the cast of The Real Housewives of New York City for its sixteenth season, which premiered on September 8, 2026.
She entered the series alongside Erika Hammond and Daisy Toye, joining returning personalities including Erin Lichy, Jessel Taank, Sai De Silva, and Carole Radziwill.
Her arrival introduced viewers to a woman with an unusual personal history and an established career outside television.
During the season, Glassman discussed her marriage, financial independence, and the difficulties of being judged for events from her twenties.
She also revealed that she maintains a separate apartment in Manhattan’s Hell’s Kitchen neighborhood while sharing another residence with her husband. The arrangement became a topic of conversation among her fellow cast members.
Who Is Hailey Glassman’s Husband?
Hailey Glassman is married to businessman Rubin Cronig. The couple have been married for approximately 15 years and have known each other since childhood.
They first met at a sailing camp on Martha’s Vineyard when they were around 12 years old. Their families lived near each other, and their early friendship eventually developed into a lasting relationship.
Cronig has business interests on Martha’s Vineyard, including Vineyard Time, a store associated with vintage watches and luxury timepieces.
Glassman has described their relationship as a lavender marriage, explaining that she also dates women while remaining married to Rubin. She has clarified that their arrangement does not involve her dating other men.
Her husband has chosen not to participate in RHONY, preferring to protect his family’s privacy and business reputation.
The couple divide their time between New York City and Martha’s Vineyard. Glassman has also confirmed that she does not have children.
Hailey Glassman’s Past Relationship With Jon Gosselin
Before becoming a Bravo personality, Hailey Glassman attracted national attention through her relationship with Jon Gosselin, who starred alongside his then-wife Kate in Jon & Kate Plus 8.
Their romance became public in 2009 during Jon and Kate’s highly publicized separation. Glassman faced criticism and speculation about the timing of the relationship.
However, she has maintained that Jon and Kate were already separated before their romance began. She has also rejected suggestions that she was responsible for the breakdown of their marriage.
The relationship ended later that year, but the publicity continued to affect Glassman’s reputation.
During her appearance on RHONY, she revisited the experience and discussed how difficult it was to be publicly judged at such a young age.
Where Is Hailey Glassman Now?
Hailey Glassman currently balances her public relations career with her growing presence on reality television. Her participation in RHONY has introduced viewers to her marriage, business interests, and lifestyle between Manhattan and Martha’s Vineyard.
She has also discussed developing a beauty-related product focused on wrinkle prevention, expanding her professional interests beyond traditional publicity.
Although Glassman became famous through her relationship with Jon Gosselin, her television return has given her an opportunity to establish a separate public identity.
At 39, Hailey Glassman is no longer simply a name associated with an old celebrity controversy. Her role on The Real Housewives of New York City has brought attention to her career, personal choices, and life with Rubin Cronig, offering a fuller picture of the woman behind the headlines.