March 22, 2023

"Why'd you have to go and make things so complicated?"
Twenty years ago, Avril Lavigne stormed onto the music scene with her debut single, "Complicated," immediately becoming pop punk's new princess. The then-17-year-old tie-wearing phenom co-wrote the hit song, which sold over 1 million copies in the U.S., and she went on to win Best New Artist in a Video at the 2002 MTV Video Music Awards. But did you know Lavigne's then-boyfriend and bandmate actually appeared in the video before they split up personally and professionally. Yeah, that is definitely complicated. 
It wouldn't be the first time that Lavigne collaborated with one of her romantic partners, the 37-year-old having met her now-fiancée Mod Sun when the pair worked on her latest album, Love Sux. Thought apparently it does not.
Look back on Lavigne's "Complicated" dating history, including her first "Sk8er Boi" and the relationship that resulted in three new tattoos…
Meet the OG "Sk8r Boi."
Avril Lavigne dated the rhythm guitarist in her band from 2002 to 2003, with Colburn leaving the group after their breakup.
"He just wanted to go do his own thing and stuff, and I mean, that happens," the "Complicated" singer told MTV News in 2004.
Talk about pop punk royalty. 
Lavigne met the Sum 41 frontman at a bar when she was just 17 years old. "I made out with him the first day I met him," she told Rolling Stone in 2011. "He gave me my first shot of Jäger. I had a tie on—it was back in the days of the tie."
But the Canadian pair didn't begin dating until two years later, with Lavigne even inking her love for the singer on her body, tattooing a small pink heart surrounding the letter "D." Lavigne and Whibley got married at a private estate in Montecito, Calif., in July 2006, where they shared their first dance to the Goo Goo Dolls' "Iris." 
But so much for their happy ending: Lavigne filed for divorce in October 2009. A source told E! News at the time that the couple had been "growing apart for months. They have become more like business partners rather than husband and wife."
When announcing their separation, Lavigne wrote on her website, "We have been friends since I was 17, started dating when I was 19, and married when I was 21. I am grateful for our time together, and I am grateful and blessed for our remaining friendship."
The duo went on to collaborate on Lavigne's 2011 album, "Goodbye Lullaby," though Whibley did legally remove "Lavigne" from his full name after adding the appellation when they tied the knot.
Lavigne's romance with The Hills alum began in early 2010, the pair showing off their bond with tattoos of each other's names later that year. MTV News reported at the time that they also got matching lightning bolt and f-bomb tats.
The couple dated for two years before breaking up in January 2012, with a source telling E! News at the time that it was "a mutual decision." And Lavigne and Jenner had nothing but love for one another, taking to Twitter refute headlines about a contentious split.
"Avril has always been there for me and is the closest person to my heart," Jenner tweeted. "I love her." Lavigne responded, "luv u 2!!! @BrodyJenner." 
Who can forget when Lavigne was part of Canada's first couple?
Shortly after her breakup with Jenner, Lavigne connected with the Nickelback lead singer in March 2012 when they worked on her self-titled album together. They started dating that July and, just one month later, Kroeger proposed. The couple got married on July 1, 2013, the date both their one-year anniversary and Canada Day. 
But after two years of marriage, Lavigne announced their split in an Instagram post. "Through not only the marriage, but the music as well, we've created many unforgettable moments," she wrote. "We are still, and forever will be, the best of friends, and will always care deeply for each other."
Keeping with her trend of remaining friendly with her exes, Lavigne told People in 2019 that she and Kroeger were still "super close. He's just always been a cheerleader of mine and always been such a huge fan. He's in my corner, he's on my side, and he's always been really great."
Lavigne began dating the son of Texan billionaire Fayez Sarofim in February 2018, with a source telling E! News that the couple met through mutual friends at a dinner party.
Though Lavigne never spoke publicly about her relationship with the businessman, the pair were photographed kissing in Italy before breaking up in May 2019
In 2020, the "I'm With You" singer briefly dated the indie musician, who is a member of Jagwar Twin, an alt-rock band that opened for her on her Head Above Water tour. The couple confirmed their romance with an appearance at Clive Davis' annual pre-Grammy gala, though neither party ever publicly commented on their relationship status. 
Perhaps is hoping the third time will be the charm.
While her latest album is titled Love Sux, Lavigne is set to once again go from "Girlfriend" to wife after getting engaged to the pop-punk singer in March 2022 during a trip to Paris. "Oui! Je t'aime pour toujours," she captioned her Instagram announcement. "Dimanche. 27. Mars. 2022."
Mod Sun (whose real name is Derek Ryan Smith) also shared the happy news on his account, writing, ""The day we met I knew you were the one. Together forever til our days are done."
The couple met met in 2020 while working on music together and began dating that November. Mod Sun co-wrote and co-produced several tracks for Lavigne's latest album, while she's featured on his single "Flames" and co-starred with him in its accompanying music video.
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