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.

Jesse Colburn was a member of Avril Lavigne's band early in the young pop-punkster's career, joining in 2002, per MTV News. Like Lavigne, Colburn is Canadian, and before playing guitar for songs like "Sk8er Boi," he was in a punk band called Closet Monster.

It wasn't long before Colburn and Lavigne made a love connection. It's a little unclear exactly when their relationship took off, but a video allegedly from 2002 shows them kissing, and in 2003, paparazzi photographed them canoodling on the beach. Lavigne was 18 at the time and Colburn was 21. However, the young romance didn't last too long. By 2004, they were broken up, and Colburn had left Lavigne's band. "He just wanted to go do his own thing and stuff, and I mean, that happens," she said in an orange carpet interview at the Nickelodeon Kids' Choice Awards that year, via MTV News.

While not a lot of insight into their relationship is out there, one can't help but wonder which Avril Lavigne songs were inspired by this teenage bandmate romance.

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.

From 2010 to 2012, Avril Lavigne dated Brody Jenner, star of the reality show "The Hills" and son of Caitlyn Jenner and Linda Thompson. Lavigne has apparently made a habit of getting tattoos to commemorate lovers. Much like when she got a "D" tattooed on her wrist for her first husband Deryck Whibley, she reportedly had Jenner's name tattooed on her torso, per MTV News. To match, Jenner got "Avril" tattooed on the inside of his right arm. The inked gesture of love came only four months into their courtship.

Their two-year relationship was well-documented as they shopped together around Los Angeles, went bowling, and hung out with Kim Kardashian and Kris Humphries (could anything be more 2010?). But Lavigne and Jenner just couldn't make it work in the long run. An anonymous insider told Us Weekly, "It was mutual, but Brody really broke up with her. ... He told her he was tired of always being her plus-one, and always going on tour with her." Despite the end of their romance, the pair has seemingly remained on good terms throughout the years. After Lavigne announced her engagement to Mod Sun in 2022, a source told In Touch, "Brody wishes nothing but great things for Avril and Mod Sun and isn't jealous about their engagement at all."

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.

While most of Avril Lavigne's relationships have been serious ones, she's also had a couple of rumored flings. In 2009, People reported that the "Complicated" singer and "That '70s Show" star Wilmer Valderrama were seen together in Los Angeles. An "onlooker" dished to the publication, claiming, "Avril had her hand on his knee at one point. They looked super cozy together. ... They were whispering close the entire night, laughing and having a lot of fun." While they may have had a brief flirtation, it was never confirmed that they were actually dating.

Singer-songwriter Ryan Cabrera was another rumored romantic interest for the pop-punk princess. Cabrera and Lavigne were openly friends, but their obvious closeness sparked dating rumors. E! News reported that after her divorce from Chad Kroeger in 2015, Cabrera moved in with Lavigne when his girlfriend didn't care for his wild lifestyle. A year later, TMZ reported that they shared a romantic dinner where witnesses saw them kiss. However, the pair never came out as anything more than a couple of musician buddies hanging out.

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.

In February 2019, Avril Lavigne revealed she had been dating a new man for a year. In an interview with "The Morning Mash Up," Lavigne explained that friends had set them up on a date and that he wasn't a musician. Media outlets were quick to identify the unnamed beau as Phillip Sarofim, a billionaire heir. According to the Daily Mail, he is also "the CEO of Trousdale Ventures, LLC, a privately held investment firm," in addition to being an active investor and advisory board member.

The pair had started dating in early 2018, but Lavigne kept her relationship with Sarofim as private as possible, telling People in early 2019, "I don't want to talk about my dating life." They were only spotted out and about a few times shopping around West Hollywood or attending select events. The privacy and out-of-the-spotlight romance didn't last for long. By November 2019, Us Weekly had reported that the couple had broken up.

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.

When Avril Lavigne started writing her album "Love Sux," she thought she might be done with love for a while. But two days later, she started working with musician Derek Smith, better known as Mod Sun, and quickly changed her mind again. "For the first time in my life, I thought I should probably be single. I got together with [Mod Sun] to write a song. We just clicked. I was like, 'Should you be doing this?' It was fun and exciting, and I decided, 'F**k it. Life's short.' I'm a Libra. I love love," she explained to People.

Avril Lavigne and Mod Sun's romance progressed over the course of 2021 as they performed together, kissed on red carpets, and posted cutesy photos of each other on Instagram. They seem to be professional and romantic kindred spirits. On Lavigne's birthday, Mod Sun called her "my soulmate, the love of my life, my favorite person in the world.....my angel" amongst a slew of other superlatives and praises in an Instagram post. 

On April 7, 2022, Mod Sun revealed on Instagram that he had proposed to her in Paris with the Eiffel Tower and the Seine as their backdrop. Lavigne announced the engagement on her Instagram as well with the caption, "Oui! Je t'aime pour toujours," which translates to "Yes! I will love you forever." Let's hope the third time's the charm for Avril Lavigne.