From 1999 to 2007, Laura Prepon dated Danny Masterson’s brother, “Malcolm in the Middle” star Christopher Masterson. In an interview with Phase9 Entertainment, Prepon revealed that Christopher was the first guy she ever dated. In addition to getting to know him through Danny, she said that their paths crossed often because “Malcolm in the Middle” and “That ’70s Show” were filmed at the same studio. “I liked him for the longest time and finally I just picked him up one night in a bar and we just started from there,” she said.
Per a 2005 ESPN article, Prepon and the Mastersons are avid poker players, and Danny often participated in the poker nights that his co-star and his brother hosted at their home. “No matter if he wins or loses, he’s always pissed off at the table, and thinks everyone plays poorly,” Prepon said of Danny’s disposition during games. When Prepon produced the E! Series “Hollywood Hold’em,” the Masterson brothers both appeared on the show.
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Despite the longevity of Prepon and Christopher’s relationship, she and Danny never officially became in-laws. But even after she and Christopher called it quits, she considered her former co-star family. “I dated his brother for nine years. I’m like best friends with his mom, so Danny really is like my brother,” she said in a 2013 AP interview. Four years later, Danny told the Daily News that he was still in regular contact with Prepon.
