‘Deadpool’s’ Ryan Reynolds Was Engaged to This Grammy-Winning Singer

Ryan Reynolds is one of today’s most popular actors. With his starring role in the blockbuster Deadpool franchise, strong social media presence that includes mercilessly teasing wife Blake Lively, and recently welcoming his third child with the actress, Reynolds is consistently making Hollywood headlines.

Though he wed Lively in September 2012, he has had other high-profile relationships in the past. He was previously married to Scarlett Johansson and briefly dated actresses Melissa Joan Hart and Rachel Leigh Cook. He also had a long-term relationship with this popular singer, to whom he was engaged.

Actor Ryan .Reynolds
Ryan Reynolds | Samuel de Roman/WireImage

Met at Drew’s

According to People, the Canadian-born Reynolds met singer-songwriter Alanis Morissette at a birthday party for Drew Barrymore in 2002. Morissette was already considered a groundbreaking artist with her landmark 1995 album “Jagged Little Pill,” and Reynolds was well on his way to making a name for himself in acting.

The couple formed a quick bond and were often vocal of their deep feelings for each other. They became engaged in June 2004. Reynolds raved about Morissette’s talent, telling People in 2005, “I love her music… It can be awkward when she walks in and I’m listening to it in my underwear dancing.”

Morissette, also a native Canadian, often commented on their shared personality traits. “We have a similar sense of humor,” she said. “He’s like a soul brother to me, except that I want to jump his bones.” She also praised Reynolds for his devotion, saying in 2005, “He’s just such a supportive creature. I feel so loved by him, in a trampoline kind of way. He’s always very happy for me.”

Ryan Reynolds and Alanis Morissette at the 2003 at the MTV Movie Awards
Ryan Reynolds and Alanis Morissette | Kevin Mazur/WireImage

Difficult breakup

Three years after their engagement, Reynolds and Morissette parted ways, according to Yahoo! Lifestyle. At the time, their representatives released a joint statement to People. “Ryan Reynolds and Alanis Morissette have mutually decided to end their engagement. 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,” the statement read.

The split seemed particularly tough for Morissette, who spoke about it to the Los Angeles Times in 2008. “I think it’s the straw that breaks the camel’s back,” the Ironic singer said. “It’s having had too many of them. And I was a full-blown love addict, so it was like, ‘I can’t keep doing this, my body can’t take it.’ Breakups are a horrible thing for almost everybody I know. For someone who is a love addict, it’s debilitating.”

She saw the breakup with Reynolds as a true turning point in her life. “I’ve been on a constant journey toward finally surrendering and hitting the rock bottom that I’ve been avoiding my whole life,” Morissette said. “So this was a huge, critical juncture for me. Everything broke, and it was an amazing and horrifying time.”

Putting it to music

Morissette took to the studio for healing and created her 2008 album “Flavors of Entanglement.” In her song “Torch,” she lamented the loss of a future with Reynolds. “I miss your warmth and the thought of us bringing up our kids / And the part of you that walks with your stick-tied handkerchief,” she sang.

The singer described her self-designed journey of recovery, revealing that it was a slow process. “I entered into my own version of rehab. I went to therapy five days a week, I journaled, I had a lot of support from this incredible group of friends,” Morissette revealed. “It was just really moment by moment, step by step, snail’s pace . . .”

Now, like Reynolds, Morissette is also married and recently had her third child. While they did not end up together, Reynolds and Morissette have clearly found their own personal happiness.