Avril Lavigne once lived a quiet life in Ontario, Canada. But with drive and determination, she transformed into an international punk rock star. Known for her baggy jeans, heavy eyeliner, and a tie around her neck, Avril brought a fresh vibe to the music industry. Over a career spanning more than 20 years, she’s had multiple hits and eight Grammy nominations. However, her love life has been a bit rockier. Over the years, she’s left a trail of heartbroken men across North America, which leads us to today’s video.
We know some of you are already saying, “But Tyga is the red flag!” Here at RRG, we often call out men in our red flag series, so we decided to change it up this time. While Tyga is known for his wild ways, Avril’s relationship history is even more dramatic. Things are about to get interesting, but before the red flags start waving
After signing with Arista Records, LA Reid and his team wanted 17-year-old Avril to be a teenage Sheryl Crow, but she forged her own identity. Her debut album, “Let Go,” released in 2002, brought us hits like “Complicated,” “Skater Boy,” and “I’m with You.” At that time, Avril was dating her guitarist, Jesse Colburn. By the release of her second album in May 2004, their relationship had ended, and Jesse left the band abruptly.
MTV.com: “He just wanted to do his own thing. It happens. Band members dating and falling in love isn’t unheard of. Take Gwen Stefani, for example. She dated her No Doubt bassist, Tony Kanal, for several years. Even after their breakup, they continued working together, keeping the band intact.”
Now, it’s unclear who ended things between Avril and Jesse, but it’s a bit strange that he left when her music was at its peak, isn’t it? Anyway, within months, Avril had moved on with Deryck Whibley of the Canadian band Sum 41. They reportedly met when she was 17, but she kept him in the friend zone until things ended with Jesse. In June 2005, 20-year-old Avril and 25-year-old Deryck announced their engagement. They tied the knot in July 2006, and Deryck even changed his name to Deryck Jason Lavigne Whibley.
If you’ve ever watched our red flag videos, you know that matching tattoos are often a bad sign for relationships. Their marriage was no exception. Months after their wedding, they were photographed spitting on photographers outside popular Hollywood night spots. And it wasn’t a one-time thing. The spitting incidents happened two nights in a row. That’s pretty nasty. Unsurprisingly, her fans were disgusted by her behavior, and Avril eventually issued a statement: “I’d like to sincerely apologize for my behavior with the paparazzi. It’s trying at best dealing with their insistent intrusions. I meant no offense to my fans, whose relationship I truly value.”
By the summer of 2009, it seemed clear that Avril and Deryck’s marriage was in trouble. There were reports of public fights, nights spent partying separately, and rumors that Avril was having an affair with Hollywood party boy Brandon Davis. Avril’s rep denied any romance with Brandon, but the rumors of trouble between her and Deryck were true. In September 2009, Avril filed for divorce after three years of marriage. In a breakup announcement on her website, Avril wrote that she had a lot of respect for Deryck, and in his announcement on MySpace, Deryck stated Avril would always hold a special place in his heart.
An insider told People magazine that Avril Lavigne married too young and eventually realized she needed to experience life without Deryck Whibley. Another source revealed to TMZ that Deryck’s heavy drinking played a significant role in their split.
Reflecting on her past, Avril shared, “I don’t regret anything that I did, and yeah, I was young, but I’m glad I did it. It was a really beautiful time in my life.”
Just days after filing for divorce, Avril transferred the deed of their multi-million dollar estate to Deryck, making him the sole owner. Although it seemed like a generous parting gift, Deryck was left with over a million dollars to pay off on the mortgage.
During the divorce proceedings, Avril was rumored to be dating actor Wilmer Valderrama in November 2009. By March 2010, she was seen leaving a Los Angeles tattoo parlor with Deryck. A few weeks later, Avril was spotted in Las Vegas with Brody Jenner, and the two were photographed getting matching lightning bolt tattoos.
Avril and Brody had a close relationship, even getting into a bar brawl together. At Hollywood’s Roosevelt Hotel, Avril was reportedly attacked by five people, and when Brody intervened, he was struck over the head with a bottle. Amidst all this chaos, Avril and Deryck’s divorce was finalized in November 2010. After two years together, Avril and Brody broke up in January 2012. A month later, she was in the studio with Nickelback’s lead singer, Chad Kroeger, and their chemistry was undeniable. Despite Nickelback’s controversial reputation, Avril and Chad got engaged in August 2012, just six months after they first met, drawing intense online criticism.
We get it, we get it, we get it. A short courtship doesn’t always spell disaster, but for Avril and Chad, getting engaged after just six months was clearly a mistake. Avril’s ex-husband, Deryck, wasn’t thrilled about her new relationship. Although they promised to stay friends, Deryck was obviously still in his feelings. First, he finally took the steps to legally drop ‘Lavigne’ from his name—what took him so long? Then, for Halloween 2012, Deryck and his girlfriend, Ari Cooper, dressed up as Avril and Chad. Yes, Deryck dressed as Avril and Ari as Chad. When Chad saw the photo online, he used Nickelback’s official social media to tweet, “Hey Deryck, love the costumes! We were going to dress up as you guys this year, but all the parties had celebrity themes.” Chad, taking shots at his fiancée’s ex-husband via his band’s Twitter account? Classic. Avril and Chad married in July 2013 in the south of France. After the ceremony, Chad told TMZ he planned to stay in the honeymoon phase with Avril forever. Two years later, they announced their separation.
Now, do you see why we questioned their six-month courtship? While Avril was handling another divorce, her first ex-husband Deryck finally got his wish and dropped ‘Lavigne’ from his last name in 2014. Both Avril and Deryck faced serious health issues. Avril was bedridden for five months before being diagnosed with Lyme disease. Deryck’s heavy drinking spiraled out of control, leading to a month-long hospitalization for acute liver and kidney failure. He was placed in a coma for a week to detox and needed extensive physical therapy to walk again. Avril supported her ex-husband during this tough time, even tweeting her support.
Avril and Chad’s whirlwind romance seemed doomed from the start. Engaged after just six months, it quickly became clear that their relationship was a bad idea. Adding to the drama, Avril’s ex-husband, Deryck, wasn’t happy about her new engagement. Despite their vow to remain friends, it was obvious that Deryck still had feelings for Avril. He finally took the step to drop ‘Lavigne’ from his last name—what took him so long? And for Halloween in 2012, Deryck and his girlfriend, Ari Cooper, dressed up as Avril and Chad. Yes, you read that right. Deryck dressed as Avril and Ari as Chad. Chad saw the photo online and used Nickelback’s official social media to tweet, “Hey Deryck, love the costumes! We were going to dress up as you guys this year, but all the parties had celebrity themes.” Chad’s jab at his fiancée’s ex-husband through his band’s Twitter account? Classic. Avril and Chad married in July 2013 in the south of France. After the ceremony, Chad told TMZ he planned to stay in the honeymoon phase with Avril forever. Two years later, they announced their separation.
Now, do you see why we questioned their six-month courtship? While Avril was dealing with another divorce, her first ex-husband Deryck finally got his wish and dropped ‘Lavigne’ from his last name in 2014. Both Avril and Deryck faced serious health issues. Avril was bedridden for five months before being diagnosed with Lyme disease. Deryck’s heavy drinking spiraled out of control, leading to a month-long hospitalization for acute liver and kidney failure. He was placed in a coma for a week to detox and needed extensive physical therapy to walk again. Avril supported her ex-husband during this tough time, even tweeting her support.
Avril dated a few people here and there, but it looked like she finally found true love in 2021 when she started working with musician Mod Sun. A source told ET Online, “Avril has a history of falling for people she works with. She loves them for their musical creativity and expression.” Tyga, you better keep Avril out of those studios and away from those guys. Even Mod Sun admitted to Us Weekly that he was starstruck when Avril showed interest in his music.
By February 2021, Mod Sun was spotted with a huge Avril tattoo on his neck, so you can guess where this story was going. They went Instagram official in September 2021. Avril admitted to Us Weekly that she tried really hard to resist their connection because of her past relationship disasters. She told Nylon magazine, “I can’t believe I’ve been hurt or mistreated by so many people. I need a break from relationships.”
So, was Avril the one getting hurt, or was she the one doing the hurting? Who knows. In the end, she decided to move forward with Mod Sun, and they got engaged in March 2022 right in front of the Eiffel Tower. But behind the scenes, their relationship was a hot mess, with on-again, off-again drama. Still, in an interview with E! News in February 2023, Mod Sun said, “I have found a partner to go through life’s chaos with.” They hadn’t set a wedding date yet, but he was excited about it and even wanted to start a family. He was also celebrating four years of sobriety and thanked Avril for being his armor against self-destruction.
But just eight days after that interview, Avril was photographed hugging Tyga outside Nobu restaurant, and they left together in the same car. And guess what? This little rendezvous happened while Mod Sun was away on tour.
The day after the photos came out, a rep for Mod Sun told People magazine that he and Avril “were together and engaged as of three days ago when Mod left for tour, so if anything has changed, that’s news to him.” But, later that same day, a source told TMZ that Avril had called off their engagement, suggesting she moved on before telling Mod Sun their relationship was over.
Another source told People magazine that Avril and Tyga were just friends and that there wasn’t a third party involved in her breakup with Mod Sun. However, Avril and Tyga were seen together in Paris at Leonardo DiCaprio’s party in March 2023. A few days later, they were photographed kissing at a Paris Fashion Week party. Mod Sun shared on Instagram that he felt heartbroken after Avril unexpectedly ended their engagement. According to a source who spoke to TMZ, the photos of Avril and Tyga in Paris were especially hurtful for Mod Sun since it was the same city where he proposed to her almost a year ago. The website mentioned that he felt Avril’s public display in Paris was a huge slap in the face, or even vengeful. Given Avril’s dating history, we predict her new fling with Tyga will last no more than six months.