A Complete Timeline Of Avril Lavigne's Relationships

When Avril Lavigne emerged as a teenage Canadian mall punk with a skateboard, wearing the iconic tie-with-a-tank-top look in her 2002 debut music video "Complicated," it was a defining moment in millennial culture. And while the world has changed a lot since her "Sk8er Boi" days, she's pretty much the same pop-punk poster girl she's always been. Her love life, on the other hand, has seen its fair share of ups and downs over the years. The singer has consistently been in relationships for as long as she's been in the spotlight, admitting in an interview with Kelly Clarkson, "I'm literally never single."

Even though her 2022 album is called "Love Sux," Lavigne is actually a die-hard romantic who believes in long-term partnerships. "Relationships are not easy, but at the same time, I do love love, and I want to be in a relationship and happy and long-term, and I'm in a really good place right now," she told Extra. Though she's been through two marriages and divorces and several other long-lasting relationships, she hasn't given up her belief in matrimony. In April 2022, news broke of Lavigne's engagement to Mod Sun. In honor of her engagement, let's take a look back on her past love interests and heartbreaks throughout the years.

Avril Lavigne started dating Sum 41 frontman Deryck Whibley when she was 19 years old, in the days when she was still sporting Converse and studded belts and claiming her "rock chick" status. The couple got engaged in 2005 and exchanged vows in 2006 in a surprisingly traditional wedding with chandeliers, white flowers, and a Vera Wang dress (via MTV News). Lavigne was 21 when she said "I do" for the first time. Whibley was 26.

The pop-punk couple gushed about their happiness for years to come, and Lavigne got a heart-shaped tattoo with a "D" in the middle. Flaunting the ink in an interview with Craig Ferguson, she told the talk show host, "I'm very happy. Things are good." But as is often the case with young love, their marriage ran its course and by 2009, the couple had split. A source told People magazine (via Hello!), "She married too young," adding, "Avril realized she needs her own life and needs to explore things without him."

The divorce, however, wasn't a dramatic one, and it appears they parted with understanding and empathy for one another. In 2019, the "Sk8er Boi" singer told USA Today that she was still close with Whibley.

By 2013, Avril Lavigne was ready to try marriage again. When she walked down the aisle this time, it was to commit to Nickelback singer and fellow Canadian Chad Kroeger. Their wedding was an incredibly romantic gothic affair in a medieval castle in the South of France. Lavigne wore a black wedding dress designed by Monique Lhuillier and carried a bouquet of black roses, per Hello!.

A little over a year into their marriage, People reported that Lavigne was spotted without her wedding ring while drinking in L.A. with girlfriends, breaking the couple's pact they had previously shared with the publication — to not drink separately. After that, it became apparent that the initial romance of the relationship was wearing off. In 2015, the split was official, and in a now-deleted Instagram post (via Bustle), Lavigne wrote, "It is with [a] heavy heart that Chad and I announce our separation today. Through not only the marriage, but the music as well, we've created many unforgettable moments. We are still, and forever will be, the best of friends, and will always care deeply for each other."

Lavigne stayed true to her word and remained friends with Kroeger. In 2019, she told USA Today, "He was with me through a lot and is a really protective person in my life. He's still like family." Lavigne seriously needs to share her secret to staying on good terms with exes.

J.R. Rotem is a music producer who has worked with a lot of big names, including Rihanna, Gwen Stefani, Nicki Minaj, Snoop Dogg, and Britney Spears, per TIME. In 2017, he became both professionally and romantically linked with Avril Lavigne. A source explained to E! News, "J.R. is a producer she's been working with. ... He's respected in the industry. Lately, they've started hanging out socially and there's definitely chemistry there. They're both so passionate about music."

That chemistry developed into more than just a working relationship. Rotem posted a photo to his Instagram (pictured above) with the caption, "Bae putting in that work," per People (the caption is now edited to remove the word "Bae"). A couple months after the initial speculation about their relationship, an E! News insider said of Rotem, "He's very supportive personally and professionally." Rotem was reportedly cheering his girlfriend on as she worked hard in the studio. It's unclear when the couple officially called it quits, but Lavigne was single and dating again by 2018.

Avril Lavigne bounced back quickly from her breakup with Philip Sarofim and showed up with a new date on her arm at a pre-Grammy party in early 2020 (pictured above). Her companion's name: Pete Jonas. People promptly confirmed they were indeed dating. The pair met on Lavigne's 2019 tour; Jonas was performing with artist Jagwar Twin, who served as Lavigne's opening act for the stretch of shows. Pete Jonas posted a photo of himself on stage with Lavigne on Instagram in October 2019, saying in his caption, "A special thank u to @avrillavigne and her crew for a month of hospitality, good company, and dank poutine."

During their gala date, E! News reported, they were "holding hands and cuddling" inside the event, and Lavigne introduced Jonas to Scooter Braun, Justin Bieber and Ariana Grande's manager. But not much more information about the development of their romance ever came out, and perhaps their flirtation didn't survive the lockdowns and dramas of 2020. Considering Lavigne began dating her now-fiance Mod Sun in early 2021, it can only be assumed that she and Jonas didn't date too seriously or for too long.