Ryan Reynolds and Alanis Morissette's Relationship Timeline: A Look Back

Few unions are purer than two Canadians in love. Case in point: Ryan Reynolds (not to be confused with Ben Affleck, by the way) and singer-songwriter Alanis Morissette. Not only did these two lovebirds date, but they were also engaged (despite never having made it down the aisle). Before their breakup in 2007, the Van Wilder star and the Jagged Little Pill artist were one of our favorite couples in the mid-2000s (besides Kirsten Dunst and Jake Gyllenhaal, of course).

At the peak of their relationship, the pair were often seen supporting each other at industry events — with a nice helping of PDA thrown in. The musician had a lot of wonderfully weird things to say about her movie star beau. She once told People she felt "so loved by him, in a trampoline kind of way." She also said that Reynolds was "like a soul brother" to her, with an important distinction, "except that I want to jump his bones." You said it, sister.

Here's a look back at Ryan Reynolds and Alanis Morissette's relationship.

February 2002: Ryan Reynolds and Alanis Morissette first meet

Apart from being Canadian, the pair had something else in common: Drew Barrymore as a friend — at least enough to get an invite to her parties. They reportedly met at the Charlie's Angels star's 27th birthday bash, according to People.

February 2003: Ryan Reynolds and Alanis Morissette are first spotted together

It was a big year out for the couple in 2003. Reynolds and Morissette made a number of appearances at award shows, festivals, and other events — Juno Awards, MTV Movie & TV Awards, and Tribeca Film Festival, to name a few — as each other's plus one.

June 2004: Ryan Reynolds and Alanis Morissette get engaged

In June 2004, Morissette and Reynolds took their relationship to the next level when they got engaged. 

"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," Morissette told People.

June 2006: Ryan Reynolds and Alanis Morissette break up

After getting engaged, Reynolds and Morissette reportedly broke up — temporarily. By July, they were spotted doing couple activities like going for strolls, holding hands, kissing — from Vancouver to New York City.

February 2007: Ryan Reynolds and Alanis Morissette break up after reuniting

Although their initial split appeared to be a false alarm, their second breakup — which came less than a year later — was official. After a nearly three-year engagement, Reynolds and Morissette announced their separation. 

"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," their reps shared in a statement to People.

It's unclear precisely what caused the split, but in true singer-songwriter fashion, Morissette channeled her post-breakup angst into music. Her 2008 album, Flavors of Entanglement, addresses the fallout, with her track "Torch" acting as the most direct link. 

She told Access of the song, "It’s really about my grief." The record boasts lyrics like, "I miss your smell, and your style, and your pure abiding way."

She admitted to Women's Health during this time that she got "angry" at herself "for staying in relationships way too long," though she never specified her romance with Reynolds.

However, it's safe to say that the high-profile aspect of her relationship contributed to its end. During an interview with Entertainment Weekly, she said she'd be "avoiding [public romance] in the future." 

"I think it's the straw that breaks the camel's back," Morissette told the Los Angeles Times of her split from Reynolds. "I was a full-blown love addict, so it was like, 'I can't keep doing this, my body can't take it.' For someone who is a love addict, [breakups are] debilitating."

He added, "I've been on a constant journey toward finally surrendering and hitting the rock bottom that I've been avoiding my whole life. So this was a huge, critical juncture for me. Everything broke, and it was an amazing and horrifying time."

Reynolds kept his emotional journey closer to the chest and began dating actress Scarlett Johansson soon after he and Morissette called it quits. News of their engagement broke around the same time that Morissette's breakup album was released, which also coincided with the release of ScarJo's debut album Anywhere I Rest My Head. Isn't it ironic? (She told Newsweek she was "really happy for him," by the way.)

Speaking of "Ironic," the only times Reynolds has spoken on the record about his ex have been really, really weird. In 2016, while promoting Deadpool on the TODAY show, he began singing along to Morissette's 1995 hit, uttering the line "Isn't it ironic?" in falsetto before asking then-host Matt Lauer, "Don't you think?"

That same year, in an interview he did as Deadpool with Entertainment Weekly, he told the publication that his favorite holiday was Alanis Morissette Day (which is a real thing, FYI). Apparently, he pulled his "Ironic" shtick during an interview in 2017, too.