Canadian actor Matthew Perry gained fame and recognition through his role as Chandler Bing on the hit show Friends. Throughout his three-decade career, Perry was romantically linked with several big names in Hollywood, including Julia Roberts and Cameron Diaz.

Perry's rise to stardom was accompanied by personal struggles, particularly his battle with alcohol addiction. In his 2022 memoir, Friends, Lovers and the Big Terrible Thing, Perry acknowledges the relationships he lost due to his addiction. He expresses gratitude to his first girlfriend Gabrielle Bober, who recognized the problem and sent him to rehab.

Tragically, in October 2023, Perry was found dead at a Los Angeles-area home. Law enforcement sources confirmed his death, reporting that Perry was discovered in a jacuzzi, with no drugs found at the scene.

Looking back at Perry's relationships, it's revealed that he had a secret make-out session with Valerie Bertinelli while she was still married to Eddie Van Halen. He also dated Tricia Fisher, the half-sister of the late Carrie Fisher, and had a brief fling with Gwyneth Paltrow. Perry's most high-profile relationship was with Julia Roberts, which ended after a few months.

He also had significant connections with Gabrielle Allan, Jamie Tarses, Rachel Dunn, Natasha Wagner, Lizzy Caplan, and Cameron Diaz.

His longest relationship was with Lizzy Caplan, lasting for six years, though they ultimately separated. Perry later dated Molly Hurwitz, whom he proposed to in 2020 but called off the engagement in 2021. Hurwitz shared her fond memories of Perry following his death and expressed her gratitude for the impact he had on her life.

Matthew Perry's journey in Hollywood was marked by both success and personal struggles, but his talent and impact on those around him will not be forgotten.