Hailey Glassman is sharing even more details about her past relationship with Jon Gosselin. The Real Housewives of New York City cast member has been so open on RHONY Season 16 about having a relationship with the reality TV personality when she was in her early 20s and is continuing to open up about her time dating her now-ex-boyfriend.
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Hailey appeared on Watch What Happens Live with Andy Cohen on Tuesday, Sept. 29, where she revealed that her mom had set her up with Jon after she said her dad performed a “tummy tuck” on Jon’s ex-wife, Kate Gosselin. “They were friends,” she said. “So then they became family friends, and then during their divorce and separation, he moved into my parents’ house. And then I came home from Indiana and a friendship bloomed into more.”
Hailey further shared more details about her relationship during RHONY Season 16, Episode 4. “At 22 years old, I got accused of ‘Homewrecking Hailey’ everywhere; that wasn’t true,” she said to Erin Lichy in the episode. “And it’s unfortunate that you have never been through something like that, where the whole world is placing a judgment and placing a false narrative on something that never happened because it changes you and it does something to you.”
Did Hailey Glassman ever address her and Jon’s relationship with his ex-wife, Kate Gosselin?
On WWHL, Hailey shared that she and Kate Gosselin didn’t discuss her relationship with Jon at that time. “She knew that wasn’t true,” she said, adding Kate “wasn’t allowed to say anything, so she had to be quiet and not say anything” given her job obligations at the time.
Hailey Glassman says she paid Jon Gosselin’s child support
Hailey spoke with Page Six‘s Virtual Reali-Tea on Sept. 29, where she says that she supported Jon financially after his divorce from Kate. “I paid his child support for a very long time during that divorce,” she told the publication. “Never got paid back, but it’s OK, Jon! I know you’re working through it… I love you forever.”
RELATED: What Does the Cast of RHONY Season 16 Do for a Living? Career & Job Details
Hailey Glassman reveals how dating Jon Gosselin changed her life forever
Although Hailey and Jon are in a good place today (more on that down below), she admitted during RHONY Season 16, Episode 2, that dating Jon led her to her marriage to her husband, Rubin. “The whole Jon Gosselin situation, if that never happened, my life would be completely different today. And when I say that, I would have never married Rubin,” she said. “I would have never chose a life based off safety and survival. I didn’t choose that life I wanted for myself, I chose a life to be safe, and to protect myself and my soul.”
RELATED: RHONY’s Hailey Glassman Explains Her “Lavender Marriage” With Her Husband (EXCLUSIVE)
Where does Hailey Glassman stand with Jon Gosselin today?
Hailey is still in a good place with Jon and his wife, Stephanie Gosselin. “We took about maybe a couple of years of not talking, and then he reached out to me apologizing to me,” she told Page Six on Sept. 29. “He wrote me a letter apologizing and this and that and then we met up, and then we just were family ever since. I’m going over there for Thanksgiving. And I love his wife, Steph, she’s wonderful.”
Hailey reunited with Jon and Stephanie in early September at the RHONY Season 16 premiere party. Stephanie took to Instagram on Sept. 15, where she posted a photo of her and Jon posing with Hailey before sharing details about their relationship in the caption of the post. “Whoever thinks you can’t be friends with people from your past, or thinks keeping those friendships is automatically a red flag, is delusional,” she wrote. “It’s called maturity, growth, and moving the hell on without having to hate each other. Imagine that!!!”
Learn more about Hailey’s career, her relationship, and her background before joining RHONY Season 16.
