The Real Housewives of New York City star Hailey Glassman has admitted she’s “deeply unsatisfied” in her 15-year marriage to Rubin Cronig and is considering whether to leave him.
During the November 10 episode of RHONY, Hailey opened up to Sai De Silva about feeling stuck in a marriage that no longer makes her happy.
Despite loving Rubin and appreciating everything he’s done for her, Hailey admitted, “I need to make a change.”
But walking away isn’t that simple. Hailey is worried about starting over after spending much of her adult life with someone she’s known since childhood.
She also admitted that she’s scared the grass might not be greener on the other side.
Why is RHONY’s Hailey Glassman unhappy with Rubin?
Hailey told Sai that their marriage now feels more like a “mother-son situation” than an equal partnership.
She explained that she’s grown and changed over the years, while Rubin has largely stayed the same. Now, she wants someone who can offer her more emotional support.
Hailey is confiding in Sai about her relationship. #RHONY is all-new TUESDAY. https://t.co/afXiuoNb33
— Bravo (@BravoTV) November 8, 2026
It’s not the first time she’s expressed frustration with their dynamic.
Earlier in the season, Hailey joked to Carole Radziwill, “Rubin is my child,” after admitting she often feels like a mother to him.
She also revealed that she maintains a separate apartment in New York City because she enjoys having her own space.
Speaking to a producer in an earlier episode, Hailey complained about doing household chores at their shared home, admitting, “I feel like a servant.”
Rubin hasn’t appeared on RHONY. Hailey previously told Bravo Insider that he wanted to protect his family’s legacy by staying off-camera.
“He didn’t want to ruin his family’s legacy,” she explained.
However, he isn’t entirely unknown. Rubin runs a watch business on Martha’s Vineyard, and a 2012 profile in The Vineyard Gazette featured his photograph and entrepreneurial background.
The couple first met at sailing camp on Martha’s Vineyard as children.
Hailey has also described their arrangement as a lavender marriage. Under their agreement, she can date women but not other men.
Despite their history together, Hailey admitted to Sai that she loves Rubin but doesn’t believe he’s the right long-term partner for her.
Is Hailey Glassman planning to leave Rubin on RHONY?
Hailey hasn’t made a final decision, but she’s seriously considering what life without Rubin could look like.
“I don’t know if I’m leaving Rubin or staying,” she told Sai.
After her highly publicised relationship with Jon Gosselin ended, Hailey moved on to her relationship with Rubin. She explained that she’s never experienced being independently single and wants to explore dating.
However, she doesn’t want an ugly divorce.
Hailey’s Husband Instagram
by u/LegionnaireHasIt in RHONY
Hailey told Sai that she wouldn’t seek money from Rubin if they separated and hopes they could preserve their friendship.
During the RHONY After Show, Hailey reflected on how Rubin supported her following her difficult relationship with Jon.
She explained that Rubin made her feel safe when she needed stability. However, the relationship that worked for her back then may no longer be what she needs now.
Hailey also acknowledged how frightening it feels to start over at 40. Still, she doesn’t want to reach 60 regretting that she never explored a different life.
The Real Housewives of New York City airs Tuesdays on Bravo.
Love to chat about Reality TV? Join us in our new Facebook group and come chat! Or follow us on Instagram, Facebook and TikTok for more entertainment news.
