As we know from his 2022 memoir, Friends, Lovers and the Big Terrible Thing, Perry’s love life was as tumultuous as it was intriguing. He has made no secret of his unrequited crush on co-star Jennifer Aniston in the early days of Friends, and then there was the string of Hollywood actresses. He clearly had charisma and charm on his side; it seems what was lacking was a basic level of self-worth.
In 2013, he famously said: “I would love to start a family of my own. I think I’d make a great dad, and I think shortly, I would make a great husband.”
It was a dream never realised, as Perry recounted in his memoir: “When I can get someone, I have to leave them before they leave me, because I’m not enough and I’m about to be found out, but when someone I want doesn’t choose me, that just proves I’m not enough and I’ve been found out.”
He went on to write, “I will leave first. I will fabricate in my mind that something went wrong with you, and I’ll believe it. And I’ll leave. But something can’t be wrong with all of them. What’s the common denominator here?”
It’s a way of thinking which, according to experts, often harks back to childhood.
“Fabricating a reason to end a relationship often speaks to a fear that a person holds about themselves, this unspoken fear that they’re not good enough,” explains Ammanda Major, Relate’s head of service quality and clinical practice.
“This lack of self-worth is often rooted in childhood, particularly when people have been raised with the feeling of shame, or where the caregiving wasn’t good enough, or perhaps where they felt they had been abandoned, and as a result, [they] internalise the feeling that something is wrong with them. And of course, with children and young people, this is just not the case. But it can be felt very deeply and can often become a self-fulfilling prophecy.
“Some people can’t trust that a partner would want to care for them, would genuinely love them. They can’t trust that they’re good enough. It can be very profound.”
Perry was believed to have been single at the time of his sudden death, instead choosing to focus on his sobriety, but here we recount the relationships that shaped Perry’s love life across the decades.
Valerie Bertinelli
Valerie Bertinelli was one of Matthew Perry's long-time crushes. Photo / Getty
A few years before he shot to fame as Chandler Bing in Friends, Perry developed a crush on his co-star Valerie Bertinelli in the short-lived 1990 sitcom, Sydney, when Perry played her younger brother.
“I fell madly in love with Valerie Bertinelli, who was clearly in a troubled marriage,” Perry revealed.
“My crush was crushing; not only was she way out of my league, but she was also married to one of the most famous rock stars on the planet, Eddie Van Halen.”
Perry went on to reveal details of one night at Bertinelli and Van Halen’s home: “As the night progressed, it was clear that Eddie had enjoyed the fruits of the vine a little too hard, one more time, and eventually he just passes out, not 10 feet away from us, but still. This was my chance! If you think I didn’t actually have a chance in hell, you’d be wrong, dear reader – Valerie and I had a long, elaborate makeout session.”
The next day, however, with Bertinelli making no reference to the incident, Perry got the hint and moved on, but not before admitting to many a “tearful” night and feeling “devastated inside”, finding relief only once the show was cancelled “and I didn’t have to see Valerie anymore”.
Jennifer Aniston
Jennifer Aniston comforted Matthew Perry as he attempted to describe what his Friends co-stars meant to him. Photo / X
But there was a time, three years before they starred together in the hit sitcom, that Perry admitted to having a huge crush on Aniston, confessing that during the first script reading of Friends in 1994, he’d ask himself: “How long can I look at her? Is three seconds too long?”
“I was immediately taken by her (how could I not be?) and I liked her, and I got the sense she was intrigued too – maybe it was going to be something,” he wrote in his memoir.
Alas, the would-be love story did not blossom, despite Perry summoning the courage to ask Aniston out. “[Jennifer] declined (which made it very difficult to actually go out with her), but said that she’d love to be friends with me.”
Eventually, Perry’s crush dissipated, with him remembering, “At some point, I had to say, ‘Enough’.”
Julia Roberts
Actor Matthew Perry and actress Julia Roberts hug each other on the set of Friends. Photo / Liaison
Perry met Roberts on set when she guest-starred in Friends in 1995. Describing an old-school romance in an era before text messages, Perry wrote: “Thus began a three-month courtship by daily faxes. This was pre-internet, pre-cellphones – all our exchanges were done by fax. And there were many hundreds.”
At the time one of Hollywood’s most bankable stars, Roberts was not immune to Perry’s trademark cold feet, and he later ended the relationship. He wrote: “Dating Julia Roberts had been too much for me. I had been constantly certain she was going to break up with me. Why would she not?”
In the end, his old demons reared their heads again, as he wrote: “I was not enough; I could never be enough; I was broken, bent, unlovable.”
Gwyneth Paltrow
Gwyneth Paltrow.
In a sea of many touching tributes to emerge following Perry’s death, it was the Instagram post by Gwyneth Paltrow that captured hearts, revealing a “magical summer” the two spent together in 1993 at the Williamstown Theater Festival in Massachusetts.
Paltrow wrote: “We were both there for most of the summer doing plays. He was so funny and so sweet and so much fun to be with. We drove out to swim in creeks, had beers in the local college bar, kissed in a field of long grass.”
The summer of love was not to last, however, as Perry was on the precipice of super-stardom. Paltrow explained: “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.”
Yasmine Bleeth
Yasmine Bleeth was name-dropped by Perry’s Friends character Chandler Bing as his ultimate crush. Photo / Getty
In 1996, Yasmine Bleeth had become a byword for desire thanks largely to her role as Caroline Holden on Baywatch. So much so that she was regularly name-dropped by Perry’s Friends character Chandler Bing as his ultimate crush. The pair are said to have dated shortly after his split from Roberts.
Nether actors ever spoke of the rumoured coupling, but Bleeth’s name remained a focal point for Friends’ script-writers, who would drop in references to her in many future episodes.
Lizzy Caplan
Matthew Perry said he almost proposed to Lizzy Caplan. Photo / Getty
Described as Perry’s “almost-marriage”, he first met Mean Girls and Fleishman is in Trouble actor Lizzy Caplan when, aged 36, he crashed her 23rd birthday party. What started as a casual fling went on to become one of Perry’s defining relationships.
Perry later revealed he had planned to propose to Caplan, having had a painting commissioned depicting the couple and the 1780 text messages they had shared during their relationship.
“My plan was to give her the painting and then ask the question… well, I never asked it,” he wrote. “I gave her the present and she was really moved by it, saying, “Matty, my little heart – what you’re doing to my little heart”, and it was time. All I had to do was say, ‘Honey, I love you. Will you…’ But I didn’t say it. All my fears reared up like a snake.”
Admitting both parties had “intimacy issues”, Perry later reflected on what could have been and said he often imagined a marriage to Caplan involving a house and two kids, but that ultimately, he missed the moment.
Molly Hurwitz
Molly Hurwitz began dating Perry in 2018. Photo / Instagram
Perry’s last-known and arguably most successful relationship started in 2018 when he began dating literary manager Molly Hurwitz, and she quickly became the love of his life. In 2020, while at a Switzerland rehab centre, he said, “I decided to get engaged. Luckily, I happened to be dating the greatest woman on the face of the planet at this time.”
What emerged was an endearingly low-key relationship peppered with the odd romantic post on Hurwitz’s Instagram page, most notably on Valentine’s Day 2020, when she wrote: “Second year being my valentine, but his first as an Instagram influencer. HVD to my favourite.”
With very little fanfare or explanation, the two called time on their relationship in June 2021, with Perry declaring, “Sometimes things just don’t work out, and this is one of them. I wish Molly the best.”
