Who Had Matthew Perry Dated? Exploring His Relationships

Matthew Perry, the late actor who made us all laugh as Chandler Bing on the hit TV show "Friends," has had his fair share of romantic entanglements in the past. He's not just known for his on-screen chemistry, but also for his off-screen relationships with some of Hollywood's leading ladies. 

Among these, Perry's been linked with the lovely Julia Roberts and the charming Gwyneth Paltrow. These real-life connections added an extra layer of intrigue to his celebrity status, making fans even more curious about the man behind his iconic sarcastic one-liners of Chandler. 

The Last Women To See Perry 

The last woman who was seen spending time with Matthew Perry before his sudden passing was Athenna Crosby, who considered him a close friend. Just a day before his shocking death, they shared a meal. Their friendship had blossomed not too long ago after being introduced by a mutual friend, and they quickly became confidants. 

AthennaMatthew Perry's friend, Athenna Crosby SOURCE: Access Hollywood YouTube Channel

According to Athenna, Perry seemed to be in good spirits during their lunch. He showed no interest in returning to his past struggles with drugs and alcohol. He appeared to be genuinely committed to his newfound passion for fitness and pickleball. She noted that the actor even refused to glance at the drink menu, highlighting his dedication to a healthier lifestyle. 

Matthew Perry's Death

The news of Matthew Perry's passing sent shockwaves across the world on that fateful day, October 28, 2023. At just 54 years old, the beloved actor was discovered lifeless in his Los Angeles home, in a stand-alone jacuzzi. Despite the initial confusion and speculation, investigations revealed no signs of illegal drugs at his residence. Moreover, a thorough autopsy conducted by medical professionals confirmed there was no trace of meth or fentanyl in his system.

The cause of Perry's demise was ultimately attributed to an apparent drowning, leaving everyone puzzled and saddened by the unexpected turn of events. As detectives continued to delve into the circumstances surrounding his death, the world remained on edge, anxiously awaiting answers to the lingering questions about the loss of a talented actor.

Perry's Past Engagement

Perry's past engagement to Molly Hurwitz was a whirlwind of emotions for both the actor and his fans. The couple's love story started back in 2018, but it wasn't until early 2020 that they publicly confirmed their relationship. With smiles and happiness, he announced their engagement in November 2020, marking a significant milestone in their journey together. 

MollyMatthew Perry's ex-fiancée, Molly Hurwitz SOURCE: Molly Hurwitz Instagram @mollyhurwitz

However, their joy was short-lived, as Hurwitz and Perry decided to part ways just seven months later in June 2021. Despite the end of their engagement, their three-year relationship left an indelible mark, reminding everyone that love, though fleeting at times, can still bring moments of genuine happiness and connection.

Hurwitz, a talented literary manager, embarked on a new chapter in her career in April 2023 when she joined Thruline, bringing her expertise and passion for storytelling to the agency. Her journey in the entertainment industry began at ICM, where she honed her skills in comedy, television, and film, as mentioned in an article by People.

Past Relationships

Tricia Fisher

Perry revealed a deeply personal chapter of his life involving Tricia Fisher, in his candid 2022 memoir, "Friends, Lovers, and the Big Terrible Thing." At the tender age of 18, he made a sincere promise to her that he intended to uphold his virginity until his wedding night. However, his resolve lasted merely two months before the intensity of their relationship led to passionate make-out sessions. 

Despite their deep connection, the pressure began to weigh on Perry and Fisher, and the relationship eventually reached a breaking point. The pair decided to part ways, but fate had other plans. They found their way back to each other, rekindling their romance. Yet, as time passed, old fears resurfaced, causing the actor to end the relationship. 

Gwyneth Paltrow

Perry found himself entangled in a brief romance with the talented actress Gwyneth Paltrow, in the summer of 1994, before the world knew him as Chandler Bing from "Friends." They met in the quaint town of Williamstown, Massachusetts, where she was performing in a play, and he was visiting his grandfather. 

GwynethGwyneth Paltrow in a Photoshoot SOURCE: Gwyneth Paltrow Instagram @gwynethpaltrow

At a lively party, amidst the laughter and chatter, Pery and Paltrow discreetly slipped away into a broom cupboard, sharing a passionate kiss. In those carefree days, they were both still unknown enough that their fleeting romance remained a secret, hidden away from the prying eyes of the tabloids. 

Gabrielle Allan

In the tapestry of Perry's love life, there was a chapter written in the subtle hues of uncertainty and self-discovery. Gabrielle Allan, a presence whose exact dates in his life remain a mystery, became an unwitting catalyst for a profound realization. 

One evening, at the tender age of 21, Perry found himself at Gabrielle's home after witnessing a captivating magic show. The absence of alcohol in her house magnified his desire, setting his blood ablaze with an insatiable thirst. For him, it was a moment of profound revelation, a stark realization that marked the beginning of his struggle with alcoholism. 

Julia Roberts

In 1995, Matthew found himself entangled in a high-profile romance with the renowned actress Julia Roberts, who had made a guest appearance on the popular show "Friends." Surprisingly, their connection ran deeper than just on-screen chemistry; it was the actor who had orchestrated Roberts' guest appearance. 

JuliaMatthew Perry and Julia Roberts in Friends SOURCE: Entertainment Tonight YouTube Channel

However, despite their shared history and obvious attraction, Perry's deep-seated insecurities cast a shadow over their relationship. He was plagued by self-doubt, constantly feeling inadequate and unlovable. Consumed by fear and convinced that he would inevitably be abandoned, he made the heartbreaking decision to end his relationship with Roberts. 

Jamie Tarses

It was in 1994 that Perry found companionship in Jamie Tarses, although the specific timeline of their relationship remained a mystery, veiled over time. Their love story unfolded against the backdrop of his battle with alcoholism. 

As Perry embarked on the challenging journey of sobriety, he realized the need for solitude and introspection. The newfound clarity brought by his sobriety demanded space for self-reflection. Thus, with a heavy heart but a resolute spirit, the late actor made the difficult decision to part ways with Tarses.

Rachel Dunn

The years 2003 to 2005 were adorned with the presence of Rachel Dunn, a woman Perry affectionately referred to as "the ex-girlfriend of his dream" in his memoir. Their relationship was painted with the hues of deep affection and genuine connection, sparking dreams of a future together. 

RachelMatthew Perry and his ex-partner, Rachel Dunn SOURCE: Nicki Swift YouTube Channel

Perry envisioned a life with Dunn that went beyond the realm of romance. He contemplated the possibility of building a family with her, a testament to the depth of their bond. But as you can tell things didn't end as he would have hoped.

Lizzy Caplan

In the chronicles of Matthew Perry's love life, a remarkable tale unfolded with actor Lizzy Caplan. Theirs was a love story that stood the test of time, spanning an impressive six years from 2006 to 2012. Their romance, marked by enduring passion and unwavering commitment, painted the canvas of their shared history. 

Together, Perry and Caplan navigated the complexities of life, finding solace in each other's arms. For six years, they shared laughter, dreams, and the warmth of love, creating a chapter in his life that would forever be etched in his heart.

The Time Perry Made Out With Valerie Bertinelli

In the annals of Matthew Perry's life, a captivating yet bittersweet tale unfolded during his time on the sitcom "Sydney" in 1990. The late actor found himself irresistibly drawn to his co-star, the enchanting Valerie Bertinelli. At the time, she was married to the legendary musician Eddie Van Halen, adding a layer of complexity to their burgeoning connection. 

One fateful evening, Perry found himself in the company of the couple, sharing an intimate moment with Valerie after Van Halen had succumbed to the effects of excessive indulgence. That night, their lips met in a passionate embrace, revealing hidden desires that had long been suppressed, as reported in Entertainment Weekly. 

Perry confessed his longstanding feelings, only to be met with mutual reciprocation from Valerie. However, the dawn brought a harsh reality, as he discovered that the enchanting connection they shared was not acknowledged by her the next day, leaving him with a heart heavy with unspoken emotions and unfulfilled longing.


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