Matthew Perry didn't just play a guy who was "hopeless and awkward and desperate for love" on TV. He lived it. Honestly, if you look at his history, the "Matthew Perry girlfriend" search term isn't just about celebrity gossip. It’s a roadmap of a man trying to find a stable anchor while his own life was frequently drifting out to sea.
He was the king of the "Friends" era, sure. But behind the scenes, his romantic life was a tangled mess of deep insecurity, high-profile flings, and one very serious attempt at marriage that happened right before the end.
Most people think of Julia Roberts when they think of his exes. Or maybe Lizzy Caplan. But the real story of the women who stood by him—and the reasons he often pushed them away—is a lot more complicated than a tabloid headline.
The Engagement That Almost Was: Molly Hurwitz
When news broke in 2023 that Matthew had passed away, a lot of eyes turned to Molly Hurwitz. She was the last woman he was publicly serious with. They started dating around 2018. Molly isn't an actress; she's a literary manager. That distinction mattered. She wasn't in the "biz" in the same way, which seemingly gave them a bit of a grounded foundation for a while.
In November 2020, Perry did something he’d never done before. He popped the question.
He told People magazine at the time that he was dating "the greatest woman on the face of the planet." It felt like the "happily ever after" fans had been waiting for. They were frequently spotted around Los Angeles, looking relatively low-key. Molly even posted a sweet Valentine’s Day tribute to him in 2020, joking about his new status as an "Instagram influencer."
But by June 2021, it was over.
"Sometimes things just don't work out," was the official line. Later, in his memoir Friends, Lovers, and the Big Terrible Thing, Matthew admitted to a much darker reality. He confessed that he actually proposed to Molly while he was in a rehab facility in Switzerland, high on 1,800 milligrams of hydrocodone. He didn't even remember doing it. When he got back to LA and realized he was engaged and living with her, the weight of that reality—and his sobriety journey—made the relationship unsustainable.
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After his death, Molly posted a tribute that was incredibly raw. She acknowledged his brilliance but didn't sugarcoat the struggle. She mentioned Al-Anon, which tells you everything you need to know about what it was like to be the "Matthew Perry girlfriend" during his final years. It wasn't just red carpets; it was a lot of heavy lifting.
The Secret Six-Year Romance with Lizzy Caplan
If Molly was the one who almost married him, Lizzy Caplan was the one who stayed the longest.
They started dating in 2006. It’s wild to think they were together for six years and managed to keep it almost entirely out of the press. No big red carpet debuts. No "insider" leaks every week. They were just two people living a life.
Lizzy was 23 when they met; Matthew was 36. Despite the age gap, they shared a very specific, sharp sense of humor. Perry wrote about a woman in his book (who is widely understood to be Lizzy) and how he almost proposed to her, too. He had a whole plan involving a painting with 1,780 hearts—one for every text they’d ever sent.
But he blinked.
He got scared. He described it as "Chandler Bing mode." He was so terrified that she would eventually realize he wasn't enough for her that he sabotaged the moment. They split in 2012. Matthew later revealed that the last time they spoke was an email where she told him she was getting married to someone else. It clearly haunted him.
Julia Roberts and the "Broken" Self-Image
Then there’s the Julia Roberts era. This is the one everyone remembers because it happened right at the peak of Friends mania in 1995.
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The story is legendary: Julia would only guest star on the show if Matthew wrote her a paper on quantum physics. He did it. They started a flirtation via fax machine (very mid-90s). Eventually, they were a full-blown couple.
But it only lasted two months.
Why? Because Matthew couldn't handle it. He wrote that dating the most famous woman in the world was too much for his ego. He was "constantly certain" she was going to dump him. So, he dumped her first. It was a classic case of "you can't fire me, I quit" applied to a relationship. He felt "broken, bent, and unlovable," and he couldn't believe a woman like Julia Roberts actually wanted to be with him.
The "Normal" Years: Rachel Dunn
Between 2003 and 2005, Perry dated Rachel Dunn, a professional volleyball player.
This relationship is often overlooked, but it was one of the few times Matthew sounded truly settled. He told reporters that Rachel had changed his outlook on life. He stopped wanting to just "hang out with friends" and started wanting to explore what a real, committed relationship looked like.
She was with him when Friends finally ended, which was an incredibly emotional and volatile time for him. While they eventually went their separate ways, it remains one of the few chapters in his life that didn't seem defined by a "big terrible thing" or a sudden, fear-based breakup.
Why He Never Married
It’s the question everyone asks: Why did he never walk down the aisle?
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Matthew was incredibly honest about this toward the end of his life. He had a pattern. He would meet a great woman, fall in love, and then the "fear" would kick in. He was terrified of being "found out." He thought that if anyone got too close, they would see the addiction, the depression, and the parts of himself he hated.
He chose to leave before he could be left.
Basically, he spent decades trying to protect himself from a heartbreak that he ended up causing anyway by being alone. By the time he was writing his book in 2022, he seemed to have a lot of regret about the women he let slip through his fingers. He wanted a family. He wanted to be a father. But his relationship with himself—and his sobriety—always had to come first, often at the expense of his romantic life.
Understanding the Pattern
If you're looking into the history of Matthew Perry's girlfriends, you have to look at it through the lens of his health. His relationships were often mirrors of his sobriety.
- The Early 90s: High-profile, fast-paced, and fueled by the sudden rush of fame (Julia Roberts, Yasmine Bleeth).
- The Mid-2000s: Seeking stability and long-term connection (Rachel Dunn, Lizzy Caplan).
- The Final Years: A desperate search for peace and a "normal" life (Molly Hurwitz).
Key Takeaways from Matthew's Journey
If we can learn anything from the way Matthew loved, it's these three things:
- Insecurity is a Relationship Killer: Even being one of the most famous men on Earth didn't protect him from the feeling that he wasn't "enough."
- Timing is Everything: You can't be a great partner if you aren't in a healthy place with yourself. His engagement to Molly is the perfect, tragic example of that.
- Humor is a Bridge: Almost every woman he was serious with shared his specific, quick-witted sense of humor. It was his primary way of connecting with the world.
Matthew Perry’s search for a partner was really a search for a version of himself he could live with. He was a man who loved deeply but feared loss even more.
For more context on his life and the "big terrible thing" he fought against, his memoir remains the most authoritative source. It’s a tough read, but it’s the only place where you get the story in his own voice, without the tabloid filter. Reading it helps you see that he wasn't just a "celeb with a dating history"—he was a guy trying his best to find a hand to hold while navigating a storm.
Check out his book Friends, Lovers, and the Big Terrible Thing if you want the full, unvarnished truth about his final years and his hopes for the future. It provides the nuance that a simple list of names can't capture.