Jon Gosselin's Complete Dating History

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. "If you had told me a few months ago, I wouldn't have believed you," she said.

Glassman denied the engagement rumors that were circulating, but it was clear the couple was in love. "We're always laughing and joking," she said. "We watch movies, play pool, and ping pong. We laugh a lot because I beat him at everything." She praised his cooking skills and added that her family adores Gosselin and thinks of him as part of the family. "They think things happen for a reason," she said.

After the breakup, Glassman told Hollywood Life what went wrong. "Jon was just compulsively lying ... constantly," she said. "He took a lot of money from me. He hurt me, and he hurt my family, which is the worst of it. I think he played the victim for so long and people were shocked when they found out Jon was the villain," she said. She also accused Jon Gosselin of trying to extort up to $100,000 from his ex-wife by threatening to call Child Protective Services, and made fun of his penis size. "He was so small I didn't think he would cheat on me," she told Steppin Out Magazine, adding, "He's hung like a nine-year-old boy" (via Us Weekly).