Hailey Glassman has made a surprising admission about how her relationship with Jon Gosselin affected her future. The RHONY newcomer said the fallout from that romance ultimately influenced her decision to enter her current marriage with Rubin. The revelation adds another layer to Hailey Glassman’s unconventional personal life, which has already become a major storyline on RHONY Season 16.
Hailey Glassman says the fallout from dating Jon Gosselin shaped her decision to marry Rubin
In a Bravo preview, Hailey Glassman reflected on the intense tabloid attention surrounding her past relationship with Jon Gosselin. She said the public scrutiny left her feeling beaten down and ultimately changed the direction of her life.
Glassman then made a striking admission about Rubin. She said that without the Jon Gosselin situation, she “would have never married” him. Instead, she described choosing a life centered on “safety and survival” after the media storm.
The RHONY star explained that Rubin came back into her life at a vulnerable time. The two had known each other since childhood and reconnected in Martha’s Vineyard. They have now been married for 15 years.
Glassman has previously described their relationship as an “unconventional marriage”. She said Rubin allows her personal freedom within agreed boundaries, although she does not date other men.
Her history with Gosselin dates back to 2009. Glassman has said they became romantically involved after he separated from Kate Gosselin. She has also rejected the old tabloid narrative that blamed her for breaking up his family.
That media attention, however, clearly left a lasting mark. Hailey Glassman said she did not choose the life she originally imagined for herself. Instead, she sought security at a time when she felt overwhelmed by public scrutiny.
Despite that history, Glassman and Gosselin are no longer openly hostile. She has recently spoken warmly about him and his wife, Stephanie.
For Hailey Glassman, the new admission reframes her marriage as a decision shaped partly by survival rather than romance alone. That complicated history now forms part of her story on RHONY Season 16.
