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In his memoir, “Friends, Lovers, and the Big Terrible Thing,” Matthew Perry candidly reflects on his romantic journey, which was far from a fairytale. Unlike his “Friends” character, Chandler Bing, who found happiness in marriage and family, Perry’s personal life was marked by painful episodes. One such instance was when he shared a kiss with his co-star Valerie Bertinelli from “Sydney,” who was then married. The aftermath left Perry devastated, as Bertinelli resumed work as if nothing had transpired.
Perry’s unrequited affection for Jennifer Aniston, his co-star on “Friends,” is another poignant chapter in his love story. Despite expressing his feelings and being met with a friendly rejection, Perry recounted in his memoir how he struggled with this dynamic, confessing, “We can’t be friends!”
While Perry did venture into relationships with notable female celebrities like Julia Roberts, Yasmine Bleeth, Neve Campbell, and Lizzy Caplan, he grappled with a recurring pattern of ending these connections. In a candid interview with GQ, Perry revealed his deep-seated fear of not being enough, fearing rejection, and how it could potentially lead him back to addiction.
As time went on, and following his journey to sobriety, Perry found himself ready to open his heart to love once more. He acknowledged that he had been the source of his relationship issues, owing to his insecurities and fear of rejection. Through introspection and growth, Perry started to identify the qualities he sought in an ideal partner — a sense of humor, inner and outer beauty, and someone who could engage in meaningful exchanges. He also became cautious about finding someone who could stand on their own financially.
With newfound confidence and a willingness to embrace love, Perry expressed his eagerness to build a family in the future. He believed he had the potential to be a great father and eagerly anticipated this next chapter in his life.
Throughout his romantic history, Perry confessed to moments of almost-marriages and missed opportunities. Reflecting on one particular ex-partner, believed to be Lizzy Caplan, he regretted not taking the step towards marriage. These contemplations led him to ponder the “what-ifs” of his life. His engagement to Molly Hurwitz in 2020, although short-lived, demonstrated his willingness to commit.
Perry’s past with Julia Roberts, another prominent figure in his life, revealed a turning point where fear overshadowed his emotions, ultimately leading to their separation. The timing of Perry’s passing, coinciding with Roberts’ birthday, added an eerie layer to this chapter of his life.
The loneliness Perry experienced was palpable, particularly when witnessing his former loves move forward with marriages and families. He described these moments as profoundly isolating, emphasizing his aversion to solitude. Even in past encounters, such as the unexpected gesture from Virginia Madsen, Perry grappled with the fear of being alone, a sentiment that took on deeper resonance in retrospect.