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[Gather.com] Jon Gosselin Talks Hailey Glassman, Engagement - According to In Touch Weekly Magazine, Jon Gosselin is engaged to his 22-year old girlfriend Hailey Glassman. He gave her a $180000 engagement ring during their trip to St. Tropez. (Way to save up money for your eight kids, buddy.) The ring was designed by Edouard Nahum and includes a skull ...