Hailey Glassman claims Martha Stewart skipped out on her bill during a pre-season cast dinner at the Polo Bar.
The “Real Housewives of New York City” newcomer, 39, said’s “Virtual Reali-Tea” podcast that the lifestyle mogul joined the group for food earlier this year before Season 16 filming began. Glassman said the cast ended up covering Stewart’s portion themselves.
“We went to the Polo Bar before filming,” Glassman recalled. “Martha stopped by, and she dined and dashed, actually. She ordered some food and we all, like, covered it.”
The dinner brought together several cast members for what would become a preview of the new season’s dynamics. Erin Lichy, Jessel Taank, Sai De Silva, Daisy Toye and Erika Hammond all joined Glassman and Stewart at the Manhattan restaurant. Glassman noted that despite the shared meal, she never ended up filming any scenes with Stewart for the show itself.
Stewart’s connection to the Bravo series runs through Toye, who joined “RHONY” alongside Glassman and Hammond as a Season 16 rookie. Toye works as Stewart’s personal makeup artist, a professional tie that has pulled the homemaking empire founder into multiple episodes.
That working relationship produced Toye’s very first scene on the show. Stewart traveled to Toye’s rent-controlled apartment for a makeup session that doubled as a gossip session about Ryan Murphy’s “Love Story.” During the visit, Stewart dropped a personal bombshell about her final conversation with John F. Kennedy Jr.
“I was with John-John the Monday before the Friday when they died. He called me,” Stewart said in the scene. She explained that Kennedy had sought her advice about George, the political-lifestyle magazine he published.
Stewart said they met for dinner that same week, and when she asked about his weekend plans, he told her he was flying his wife Carolyn Bessette and her sister Lauren to a wedding in Martha’s Vineyard. Stewart claimed she suggested he bring a co-pilot, but Kennedy allegedly told her he didn’t need one. The three died in a plane crash on July 16, 1999.
The makeup appointment scene has opened the door for Stewart to keep popping up throughout the season. Toye has called her for cooking advice, and the two were shown grabbing a meal together in a recent episode. Glassman did not specify whether Stewart paid her own way at that later outing.
Stewart’s Polo Bar visit came before cameras started rolling on the revamped “RHONY,” which underwent a full cast reboot after the original iteration ended in 2021. The new season features an entirely fresh lineup of New York women, with returning production and a shift back toward the city’s social scene after years of pandemic-era restrictions.
The dinner incident adds an unexpected wrinkle to Stewart’s otherwise cooperative relationship with the franchise. A self-made billionaire who built her brand on impeccable presentation, Stewart has leaned into television appearances across networks in recent years, including a high-profile partnership with Snoop Dogg and competition show judging gigs.
Glassman’s claim arrives as “RHONY” continues rebuilding its audience with the new cast. The series originally premiered in 2008 and became a flagship Bravo property before ratings declines and cast departures led to the complete overhaul. Season 16 represents the first full season with the rebooted ensemble.
Toye’s dual role as cast member and Stewart’s employee has given the show access to a celebrity outside the traditional Housewives orbit. The arrangement echoes past Bravo series that brought famous names into the fold through assistant or employee relationships, though Stewart’s level of fame and established media presence set her apart from typical guest appearances.
Stewart has not publicly responded to Glassman’s characterization of the Polo Bar evening.
“The Real Housewives of New York City” airs Tuesday nights at 8 p.m. ET on Bravo, with episodes streaming on Peacock the following day.