Romance Rewind: Ryan Reynolds and Alanis Morissette’s Unlikely Relationship, Engagement

It’s hard to believe that there was ever a time when Ryan Reynolds and Blake Lively weren’t joined at the hip, but way back in the early ‘00s, Reynolds had another high-profile partner: Alanis Morissette, one of the most successful female musicians of the '90s. In fact, they were even engaged. And the couple weren’t shy about their love, PDA-ing all over every red carpet that would have them.

How it Began

This is cuter than any Marvel origin story — they met at Drew Barrymore’s 27th birthday party! The year was 2002 and while "You Oughta Know" singer Morissette, 28 at the time, was five albums into her music career, Reynolds, then 25, was a little less established. He had starred in Two Guys and A Girl and was about to find success through Van Wilder, but wasn’t quite the household name and big box office draw he is today.

After being introduced at the birthday bash, the pair bonded over being single, cute — and Canadian! “We already started off with the shorthand, so I think it’s a really great base,” said Morrissette, who began her showbiz career as a teen actress. “I attempted dating many American men. I tried!” Within a few months of first meeting, they were a certified celebrity couple.

How Long it Lasted

It’s hard to believe now, but this relationship was serious — and seemed like it was for keeps. In 2003 the couple were everywhere, clearly secure enough in their union to go as public as it comes at events like the MTV Movie & TV Awards and Tribeca Film Festival. Then, in June 2004, they got engaged, with Reynolds even flying to Ottawa to ask Morissette’s parents for permission! But the couple never got around to setting a date because, according to Reynolds, “we feel like we’re already married.” But sadly they never were, confirming their split in February 2007.

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How it Ended

After rumors of rockiness a few months previously, the couple’s official break-up came exactly five years after that first intro chez Barrymore. And they were a big enough deal at the time that their reps issued a joint statement to the press. “Ryan Reynolds and Alanis Morissette have mutually decided to end their engagement,” it read. “They remain close friends and continue to have the utmost love and admiration for each other. They ask that their privacy be respected surrounding this personal matter.” It was a sad end to what seemed like a steady, mutually adoring love affair.

And if you thought Taylor Swift invented painfully honest breakup albums, think again — Morissette poured her heartache into her music and confirmed that her 2008 album Flavors of Entanglement was inspired by the split, particularly the song "Torch," which featured lyrics like “I miss your smell, and your style, and your pure abiding way” and “I miss your warmth and the thought of us bringing up our kids."

“It was cathartic,” Morissette told Access Hollywood. “It’s really about my grief. I think the most painful, sort of suffering oriented moments in my life [are] when I’m resisting something. If I just say, ‘It’s true. I’m unbelievably insecure, really broken, devastated,’ then I can move through it, toward the next place. But if I keep resisting it, I’ll stay there forever.”

In a brutal twist — perhaps not unlike finding a black fly in your Chardonnay — the heartbreak album dropped the same month that Reynolds announced his engagement to Scarlett Johansson (they quickly married in September 2008, but separated just over two years later.)

Despite her pain, Morissette was dignified about it, telling the AP at the time, “I wish anyone whom I love, whether I hang out with them or not, great success and love in their life.”

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What They Said About Each Other

During their relationship, Reynolds and Morissette were pretty open about their feelings — and very funny with it. “He’s just such a supportive creature,” Alanis told People in 2005. “I feel so loved by him, in a trampoline kind of way. He’s always very happy for me. We have a similar sense of humor. He’s like a soul brother to me, except that I want to jump his bones.”

She added: "We have the perfect combination of compatibility and incompatibility that makes the relationship very passionate. It's perfect. I think it's about stretching each other."

Reynolds was openly in awe of his partner too, saying “Oh yeah, I love her music. It can be awkward when she walks in and I’m listening to it in my underwear dancing.”

What They Say Now

Both parties have been through several relationships since the split, with Reynolds ultimately marrying Lively in 2012 — two years after his divorce from Johansson — and Morissette heading down the aisle with hip hop artist Mario John Treadway (known as Souleye) in 2010. But still, they have referenced each other in interviews from time to time.

In 2008, Morissette told Entertainment Weekly that the breakup had put her off high-profile relationships. “Public romance? I’m going to be avoiding that in the future,” she said. “I think the only time I’ll talk about any guy I’m with will be when I’m married with six kids.” Now 50, she has three with Souleye: son Ever, born in 2010, daughter Onyx, born in 2016, and son Winter, born in 2019.

On brand as ever, Reynolds, now 47, is more lighthearted, singing along to Morissette’s best-known song, "Ironic," while promoting Deadpool in 2016, and later telling Entertainment Weekly that his favorite holiday was Alanis Morissette Day (March 8th, in case you’re curious. Yes, it’s a real day!)

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Key Relationship Takeaways

These two were obviously so in love but, while Morissette was clearly hit hard by the breakup (she told the Los Angeles Times that she hit “rock bottom” and that “it was an amazing and horrifying time”), Reynolds moved on quickly. Many of Morissette’s fans took it personally, too, bemoaning the fact that an archetypal high school hottie had moved on from a kooky, creative type to classic Hollywood beauties like Johansson and, later, Lively. It was a slap in the face, how quickly she was replaced, for sure!

Still, Morissette got some great songs out of the split, and both have clearly found long-lasting happiness with their spouses — and, admirably, they have both only ever been kind about each other, at least on the record. Plus the thought of them still being together now just feels really weird … don’t you think?