Hailey Glassman Talks Lavender Marriage: Who Else Has She Been With?

Hailey Glassman’s casting on The Real Housewives of New York City had everyone talking before she ever said a word. Now that the premiere has dropped, all anyone can talk about is her very personal confession. During the season 16 premiere, Glassman opened up about her “lavender marriage.” Now that everyone knows her marriage is unconventional, they can’t help but compare it to her last high-profile romance.

Hailey Glassman discusses her ‘lavender marriage’

Hailey Glassman is coming into The Real Housewives of New York City with a bang, but she’s keeping an air of mystery around her marriage. Glassman, 39, used the premiere to announce she was in a lavender marriage, explaining that she has intimate relationships with women, despite being married to a man. Glassman did not elaborate on their particular arrangement and has been careful not to reveal the identity of her husband, noting that he doesn’t wish to be filmed, nor have his identity revealed. She did say they grew up together, taking sailing lessons as kids, and that they’ve split most of their 15-year partnership between New York City and Martha’s Vineyard. Glassman did drop one breadcrumb. She said her husband owns a large business on Martha’s Vineyard.

So, what exactly is a lavender marriage? What it means differs from person to person now, but it traditionally refers to a marriage where one or both partners are part of the LGBTQ+ community. It was, at one time, used to conceal a person’s sexual orientation, or advance career or family reputations. Lavender marriages were also entered into to avoid social stigmas around being unwed. The practice was widely adopted during the Golden Age of Hollywood, where strict morality clauses pushed entertainers toward traditional marriage. It’s assumed it existed as a practice long before then.

She previously dated Jon Gosselin

Hailey Glassman’s confession has people looking back at her other romances. One relationship, in particular, thrust her into the spotlight when she was still rather young. In 2009, she connected with Jon Gosselin during his split from Kate Gosselin. The pair met when Hailey’s father, a plastic surgeon, provided Kate free services after she showed off her post-sextuplet stomach on her TLC series.

Following Jon and Kate’s split, Jon temporarily moved in with the Glassmans. That is when he and Hailey, then 22, reconnected. “He was living in my house, the person I joked around with. He was sad and bored; I was home and bored,” Hailey later explained. She’s also said the relationship happened partly at her mother’s encouragement, recalling on RHONY that her mom described Jon as “a great guy” and pushed her to date him.

The romance began just a month before Jon and Kate publicly announced their divorce. While allegations of cheating swirled, she has consistently denied that she had anything to do with the end of his marriage. Despite her repeated rebuttals, she was eviscerated in headlines. The relationship ended by December 2009, and Hailey later made a string of public digs at Jon, indicating the relationship had not ended on a positive note.

While Glassman moved on and out of the tabloid headlines after the end of that romance, she made a career out of public relations. Now, she’s joined the cast of The Real Housewives of New York City. While her husband wants no part of the series, her early confession has fans assuming they’ll learn more about him, whether he wants the world to know him or not.