From Julia Roberts to Selma Blair: Matthew Perry's famous girlfriends

"My oldest boy friend. All of us loved Matthew Perry, and I did especially. Every day. I loved him unconditionally. And he me. And I’m broken. Broken hearted. Sweet dreams Matty. Sweet dreams."

Selma Blair's farewell to Matthew Perry on Instagram left many stunned, revealing a hidden romance few knew about.

Photo: Instagram - @selmablair

Perry, renowned for playing Chandler Bing and sharing the stage with Joey (Matt LeBlanc), was famously pegged as the funny friend and not the romantic interest. However, in real life, his love life was full of interesting and famous women, and that's despite his substance abuse. He

But what many don't know is that Matthew Perry started ‘Friends’ as one of Hollywood's dashing young heartthrobs. His charm was not confined to the screen; his off-screen romantic escapades are also noteworthy and filled with love and heartbreak. Here are some of his many high-profile relationships.

In his memoir, ‘Friends, Lovers, and the Big Terrible Thing,’ Perry candidly discusses his renowned exes, paying significant attention to one in particular: 'Mean Girls' actress Lizzy Caplan.

"I often think if I'd asked [her to marry me], now we'd have two kids and a house," he wrote. "Instead, I'm some schmuck who's alone in his house at 53."

A six-year romance flourished between the pair, but Caplan, being 13 years younger, decided to end their relationship in 2012, a heartbreak Perry never truly recovered from. He said his fear of marriage ultimately led to their separation.

Tracing back to the late 80s, Perry’s first known girlfriend was Tricia Leigh Fisher, Carrie Fisher’s stepsister. At 19, Perry found solace and support in her amidst his struggles with alcohol-induced im-potence.

His memoir reflects on their intimate moments, describing his first time as "sheer glory, for two whole minutes!" Despite this, he admits to ending things with Fisher due to his desire to explore relationships with other women.

Fast forward to 1990, Perry found himself enchanted by Valerie Bertinelli on the set of ‘Sidney.’ However, a complicated triangle unfolded as she was married to rock legend Eddie Van Halen.

Matthew Perry shared a memorable make-out session (right next to Van Halen while he was passed out!) that left him wondering if the feelings were mutual. The aftermath was a day on set filled with unmet expectations and internal devastation as nothing changed between him and Valerie, leaving Perry heartbroken.

Fast forwarding five years to 1995, Perry recounts a three-month romance with Julia Roberts, the reigning "America's Sweetheart" of time time. This label weighed heavily on Perry, already a Hollywood star but seemingly eclipsed by Roberts’ radiant presence.

Navigating a relationship with her proved overwhelming, as Perry perpetually feared an imminent breakup. His memoir reveals deep-seated feelings of inadequacy and internal turmoil during this period and how he feared Roberts was "slumming it" by dating him.

A distinctive episode involved Gwyneth Paltrow, as revealed in his memoir. A spontaneous encounter between the two, before they were enveloped in the glow of stardom, marked a brief but memorable chapter in Perry’s romantic history.

After Perry died, Paltrow also opened up about what the two of them had back in 1993. “We drove out to swim in creeks, had beers in the local college bar, kissed in a field of long grass. It was a magical summer,” she said on Instagram. “He had shot the pilot of Friends but it had not aired yet. He was nervous, hoping his big break was just around the corner. It was.”

Following his time with Roberts, Perry engaged in a discreet yet passionate several-month romance with Yasmine Bleeth, famously known for her role in ‘Baywatch.’ This relationship unfolded in the embrace of privacy despite Bleeth’s global allure in the 90s.

A fleeting romance blossomed with Neve Campbell on the set of ‘Three to Tango,’ where reel life affection spilled into real-life passion. However, the curtains closed on their romance with the conclusion of filming.

A more tempered recollection is shared about a date with Cameron Diaz. Perry nostalgically remembered an evening marked by a lack of mutual romantic interest, despite maintaining a positive memory of the encounter.

Destiny intertwined Perry’s path with Jennifer Aniston, initially marked by unreciprocated interest before ‘Friends.’ Fate, however, cultivated a lasting friendship through their shared journey on the series.

Molly Hurwitz, a literary agent, marks the final chapter of Perry’s publicly known romantic journey, sharing a relationship from 2018 to June 2021.

Post-breakup, the couple preserved their friendship, marking a period of solitude in Perry’s romantic life, with no subsequent public relationships unveiled after Hurwitz and until his tragic death.