Friends actor and everyone’s favorite, Chandler Bing, aka Matthew Perry, was someone who faced a lot of ups and downs in his life. Even after achieving much fame during the 90s, he dealt with his own demons of addiction and health issues. Before his passing, the actor had written his memoir, mentioning unknown details of his life.
In his 2022 book, Friends, Lovers, and the Big Terrible Thing, he divulged quite a lot of secrets and personal moments. One such experience was related to his relationship with an ex-girlfriend, his almost-engagement, and his biggest heartbreak. This was his ‘Chandler Bing’ moment, as in, he managed to fumble and ruin a good thing because of panic and insecurities.
A relationship marked by turmoil: Lizzy Caplan
Before his failed engagement to Molly Hurwitz, Matthew Perry had almost proposed to another woman way back around 2012. The Friends alum met Lizzy Caplan in 2006, and it was a different sort of ‘meet-cute’ (as per New York Post).
In fact, I knew she was twenty-three because I’d crashed her twenty-third birthday party.
While he never explicitly mentioned Caplan‘s name in his book, various references pointed to the actress. He penned down their first meeting, and his concern about their apparent age-gap: she was 23 whereas Perry was 36.
Our subsequent initial make-out session was in the back of a really messy Toyota. When we were done, I said, ‘I’m gettin out of the car now. Mostly because I’m thirty-six.’
The actor went on to describe the haphazard nature of the relationship; neither of them were ready to commit or to put labels on it. They were passionate, but each had their own insecurities and issues.
We were on the same page. We never went to dinner, we never talked about each other’s families. We never discussed what went on in each other’s lives regarding other people.
Eventually, after two years, the pair made things official. Perry said he was in love, and Caplan didn’t deny that the feelings were mutual. But the following Christmas changed the course of this relationship for the worse.
The proposal that never was: the missed opportunity
That December, Perry recalls in his memoir (as per Showbiz CheatSheet), he wanted to bend the knee and pop the question. The actor mentioned feeling an immense love for his partner, the kind he could no longer deny. He organized an elaborate gift to ask the question.
I loved this woman, and I wanted her to know it.
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.
The Fools Rush In actor hired an artist and commissioned him to create a beautiful painting related to their bond. But unfortunately, his years of insecurities, panicking nature, and habit of overthinking took control.
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. I immediately went into Chandler [expletive] Bing mode. ‘Hey, hey, hey!’ I said to her consternation, ‘Look at this!‘
He couldn’t do it, and although he gave no real cause for the fumble, he just missed the biggest opportunity of his life. Later on, due to various problems and his prolonged difficulty with intimacy (due to alcohol), the pair eventually separated in 2012.
After a while, the Mean Girls actress began dating Tom Riley; Perry had invited her to watch a play he was in. But in return, the actor received an email that broke his heart, and the two never met again.
I replied that I was a little hurt that she couldn’t make it — the play was being performed in her town, for God’s sake — and then a while later I got back an email telling me that she was getting married and that she had no room in her life for friends.
This blunt refusal hurt him, along with the cruel fact that the woman whom he loved for six years was going to marry someone else. Though they never met again, he always wished her the best. To this day, Caplan has not commented on the actor’s unfortunate passing, leaving fans to wonder what could have been if only Perry had the courage to propose.
