
Credit: Instagram
Hailey Glassman has been outed for her past trolling behavior on Instagram by influencer and podcast host Claudia Oshry, aka Girl With No Job.
Just hours after the 39-year-old ex-girlfriend of Jon Gosselin, 48, was announced as part of the Real Housewives of New York City season 16 cast, Claudia, 31, leaked a series of DMs in which Hailey was seen shaming her in many ways, taking aim at her voice, her weight, and even her husband, Ben Soffer, 33.
“I know Hailey Glassman. She has been a troll of mine, like a deep internet troll since 2017,” Claudia shared in a video posted to her TikTok account on March 2.
She then shared a series of messages she received from Hailey, including one on December 20, 2017, which read, “Omg your voice is so annoying. Like Janice from Friends,” and another sent 10 days later that said, “Damn, you were thin,” following an apparent throwback photo.

Years later, following Claudia’s weight loss, Hailey became friendlier, telling her in a July 1, 2023, message that she was a “skinny Minnie now.”
But her kindness didn’t last.
“Looks great but you gotta own you’re on Wegovy,” she declared in another message, as Claudia clarified that she was on Ozempic. “You’re an influencer and you really should be honest on your platform about it. When you need any skin tightening since you def lost enough to need it, I’ll set you up with great plastic surgeon in NYC.”

Hailey additionally promoted Glassman Plastic Surgery as she encouraged Claudia to get a neck lift.
“Incredible shrinking woman … Once you get to where you want, we’ll take care of you for a 30’s neck lift,” she wrote.

As the messages continued, Claudia’s husband, Ben, caught a stray on November 15, 2024, when Hailey shaded his “dad bod.”
Though Hailey again took a turn for the nice in November 2024, when she congratulated Claudia on her pregnancy, she was back at it in June of last year when she commented on her weight.
“So weird how you were skinnier pregnant than you were [two] years ago not pregnant. You’re a magician! Congrats Momma,” she stated.

In closing, Claudia wondered why Bravo sought Hailey for their show.
“I don’t know what barrel Bravo was scraping the bottom of when they casted this person, but like, it’s giving [Monica Garcia] from [The Real Housewives of Salt Lake City],” she concluded.
@girlwithnojobNot to make everything about me….♬ original sound – Claudia Oshry
The Real Housewives of New York City season 16 is expected to go into production sometime this week.