Matthew Perry met Lizzy Caplan while he was filming Aaron Sorkin's "Studio 60 on the Sunset Strip" in 2006, which was being shot near where the "Mean Girls" star was filming the CBS' sitcom "The Class" at the time, TMZ reported. The two were formally introduced by Andrea Anders, who had recently started dating Perry's friend and former "Friends" co-star Matt LeBlanc and was starring alongside Caplan in "The Class." With initial introductions out of the way, Perry and Caplan began to spend their free time on-set together, the outlet detailed.

Perry and Caplan were notoriously private about their relationship — an arrangement that seemed to work them. The two were together for six years, quietly calling it off in 2012. And by quietly, we mean exactly that. The media only caught wind of the news the following year. "It happened a year and a half ago," an insider told Us Weekly in October 2013. "They haven't been together for a long time."

Perry and Caplan decided to part ways when the "Masters of Sex" star shared her desire to settle down. "He wasn't ready to make the full commitment so they split ... It was hard for them to let go but ultimately Lizzy decided she wanted more," a source told the Daily Mail that month. The source was unsure if Perry didn't think Caplan was the one or if he simply wasn't the marrying type. One of his former girlfriends has a theory.

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