55 Vicodin & a quart of vodka: The most shocking tales from Matthew Perry’s tell-all memoir. Read more about Matthew Perry’s life and struggles: The Massachusetts-born actor began dating Caplan in 2006, and the two managed to keep their relationship largely out of the spotlight. Perry dated “Mean Girls” star Lizzy Caplan for six years, making their romance his longest to date. 9 Perry’s longest relationship was with actress Lizzy Caplan.
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