Matthew Perry's Dating History: From Julia Roberts To Lizzy Caplan

Matthew Perry, best known for his role as Chandler Bing on the iconic sitcom "Friends," had a complex and often tumultuous romantic life. He was not just a beloved actor but also a man who navigated the challenges of fame, love, and personal struggles. Despite being linked to several high-profile women, including A-list stars and co-stars, Perry was notoriously private about his love life, often downplaying the rumors that surrounded him.

As we delve into the timeline of Matthew Perry's dating history, it becomes clear that his relationships were as varied and colorful as his on-screen characters. From his first love to his longest relationship, Perry's romantic adventures were filled with both joy and heartache, reflecting the complexities of life in the spotlight. Let's take a closer look at the women who entered and exited his life, each leaving a mark on his journey.

Tricia Fisher
Gabrielle Allan
Valerie Bertinelli
Gwyneth Paltrow
Julia Roberts
Yasmine Bleeth
Neve Campbell
Jamie Tarses
Natasha Wagner
Maeve Quinlan
Heather Graham
Rachel Dunn
Cameron Diaz
Lizzy Caplan
Molly Hurwitz
Rumored Flings

Tricia Fisher

Matthew Perry's first notable relationship was with Tricia Fisher, the half-sister of Carrie Fisher. Their romance blossomed when Perry was just 18. In his memoir, he shared that he initially claimed he would remain a virgin until marriage, a cover for his insecurities related to alcohol and intimacy.

Despite his fears, Tricia helped him realize that he was capable of a physical relationship, leading to a brief but impactful romance. Their relationship lasted a few months before they parted ways, but they later rekindled their romance while Perry was starring in "Friends." Unfortunately, old insecurities resurfaced, and they split again, marking an early lesson in love and vulnerability for the young actor.

Gabrielle Allan

Following Tricia, Perry dated Gabrielle Allan, a writer and producer known for her work on shows like "Scrubs" and "Veep." Their relationship took place around 1990 when Perry was 21, a time when he was starting to recognize the effect of alcohol on his life.

During their time together, Perry experienced a turning point as he acknowledged his struggles with alcohol. He realized that his love for drinking was controlling him, and it was during a night out with Gabrielle that he fully grasped the depth of his addiction. This relationship served as a catalyst for his lifelong battle with substance abuse.

Valerie Bertinelli

In 1990, Perry found himself smitten with co-star Valerie Bertinelli while filming the sitcom "Sydney." Despite her being married to rock star Eddie Van Halen, Perry fantasized about a life together. Their chemistry culminated in a passionate make-out session one night when Van Halen passed out from drinking.

Although it felt like a dream come true for Perry, he was left heartbroken when Bertinelli didn’t acknowledge their encounter the following day. This fleeting romance highlighted the complexity of relationships in Hollywood and the challenges of navigating feelings when fame is involved.

Gwyneth Paltrow

Among the most memorable romances in Perry's life was his brief fling with Gwyneth Paltrow in the summer of 1994. They met in Williamstown, Massachusetts, where Paltrow was performing in a play and Perry was visiting his grandfather. Their playful encounter at a party, where they sneaked off to make out, was a sweet escape before Perry's rise to fame with "Friends."

Years later, Paltrow fondly remembered their time together, stating that it was a magical summer filled with fun adventures. Perry's lighthearted recollections of their romance showcased a more carefree side of his life before the pressures of fame took over.

Julia Roberts

In 1995, Perry's high-profile romance with Julia Roberts made headlines when she guest-starred on "Friends." Perry had orchestrated her appearance on the show, leading to their whirlwind romance. Their connection was strong, but Perry's insecurity led him to end the relationship, fearing that Roberts would leave him.

This relationship provided insight into Perry's struggles with self-worth and anxiety, revealing the emotional turmoil that often accompanied his romantic endeavors.

Yasmine Bleeth

Chandler Bing would have been envious of Perry's romance with Yasmine Bleeth, known for her role on "Baywatch." Their relationship in 1996 lasted a few months, and although they kept things quiet, Perry's admiration for her was clear. Their connection was referenced in "Friends," showcasing how intertwined his real-life experiences were with his character.

While this romance was shorter than others, it demonstrated Perry's ability to attract notable women, further solidifying his celebrity status.

Neve Campbell

Perry's on-screen chemistry with Neve Campbell in the movie "Three to Tango" led to a brief romance in 1999. Their relationship was sparked during filming, but it ended before the movie's release. Despite the short duration, their rapport hinted at a deeper connection, with both enjoying the industry camaraderie.

The film's lackluster reception contrasted with the genuine connection they shared, emphasizing the unpredictability of Hollywood romances.

Jamie Tarses

Jamie Tarses, a powerful TV executive, and Perry had a relationship that intertwined personal and professional realms. Their bond was significant enough that Perry described her as a "sort-of girlfriend" in his memoir. After he fell ill, Tarses rushed to his aid, demonstrating the depth of her care for him.

Ultimately, Perry made the difficult decision to end the relationship to focus on his sobriety, highlighting the sacrifices made in the name of personal growth.

Natasha Wagner

Following his breakup with Jamie, Perry briefly dated Natasha Wagner, daughter of actors Robert Wagner and Natalie Wood. In his memoir, he reflected on the possibility of a future with her but recognized that he wasn't ready for that commitment. Their romance was short-lived but left a lasting impression on Perry.

Years later, learning about Natasha's motherhood stirred feelings of regret in Perry, showcasing his vulnerability and desire for connection.

Maeve Quinlan

Perry's relationship with Maeve Quinlan lasted from 2002 to 2003 and was marked by public appearances that hinted at a serious commitment. They shared a love for tennis and were often seen together at events, showcasing a more playful side of Perry's romantic life.

Despite their bond, the details surrounding their breakup remain private, though they seemed to part on good terms, as they were spotted together years later.

Heather Graham

In 2003, rumors linked Perry to actress Heather Graham, though their relationship was brief. They were seen together at events, suggesting a friendly rapport that may have developed into something more. Despite the timing of their rumored romance, they managed to maintain a level of privacy amidst the media's scrutiny.

Their amicable interactions post-breakup demonstrated Perry's ability to navigate relationships gracefully, even when the romantic aspect faded.