Hailey Glassman is not letting old tabloid headlines follow her onto RHONY without a fight. The Real Housewives of New York City newcomer used her premiere episode to set the record straight about her 2009 relationship with Jon Gosselin, and how the fallout from it shaped the rest of her life.
Setting the Record Straight on “Home-wrecking Hailey”
Glassman, 39, met Jon through an unusual connection. Her father, a plastic surgeon, performed Kate Gosselin’s tummy tuck after she had her sextuplets. The families became close. According to Entertainment Now, Glassman said her mother actually pushed her toward dating Jon, calling him a great guy.
Glassman was 22 and had just come home from college in 2009. She and Jon had already been friends. That friendship turned romantic once he separated from Kate. Glassman has maintained the relationship began months after the split, even though it became public before the divorce was officially announced. “Mistress Hailey. Home-wrecking Hailey, The Mistress That Ruined a Family of 8. It wasn’t even true,” she said on the show, describing the nickname the press gave her at the time.
How the Tabloid Attention Actually Affected Her
Photos of Glassman and Jon on her father’s yacht ended up on TMZ. From there, the story spun out of her control. She said reporters even showed up at Indiana University, where she was a student, and tried paying other students for gossip about her.
Glassman described the toll it took on her in blunt terms. “The media was just destroying me, and at 22 you don’t know who you are,” she said. She compared the experience to losing a piece of herself with no way to properly grieve it. She and Jon broke up before the end of 2009, together for less than six months total.
How It Led Her to Her Husband
Dating Jon led Glassman to Martha’s Vineyard. There, she reconnected with Rubin, her now-husband. The two had actually known each other since childhood, meeting at sailing camp when they were 12. She has said that without the Gosselin chapter of her life, she likely never would have married him.
Glassman also opened up about their marriage itself, which some outlets have described as a lavender arrangement built more on safety and trust than a typical relationship. She said Rubin lets her live her life, with one condition: she doesn’t date other men. She was clear that it isn’t a polyamorous setup, just an arrangement that works for both of them.
Notably, Glassman is still close with Jon and his wife, Stephanie Lebo. Lebo showed her support after the premiere. She posted photos from Glassman’s launch party. She said that old exes staying friends is a sign of maturity, not a red flag.
Sarah covers Sister Wives, Teen Mom 2, Real Housewives, and Big Brother. She specializes in cast updates and recaps, with a steady eye for the details longtime fans notice first. Sarah has written about reality TV and entertainment for four years.
