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Hailey glassman, a family friend who is 10 years jon’s junior, and the former reality star dated sometime after his split with kate until their breakup in december 2009. 2 minutes kate gosselin is reportedly threatening to subpoena hailey glassman, jon gosselin’s former girlfriend, in her lawsuit against jon and author … While reeling from his divorce from kate gosselin, jon gosselin began dating longtime family friend hailey glassman

Glassman, who is 10 years jon's junior, told people she never expected their friendship to turn into anything more. “we remained in bed, and jon called kate on speaker phone. Hailey glassman, a household good friend who is ten years jon’s junior, and the previous truth star dated at some point after his split with kate till their separation in december 2009

In march 2011, glassman told radaronline that jon when tried to blackmail kate

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