Avril Lavigne’s love life has been full of rockers and rappers.

The Canadian musician was engaged to singer Mod Sun for 10 months before the couple called it quits in February 2023. A source told PEOPLE that the pair were “on and off for the past two months, but are no longer together as a couple.”

Lavigne and Mod’s breakup made headlines one day after the singer was spotted hugging rapper Tyga at Nobu in Los Angeles. Lavigne and Tyga dated for three-and-a-half months before splitting in June 2023. They reunited a month later, only to break up again in October 2023.

The “Complicated” singer was previously married to Sum 41 singer Deryck Whibley from 2006 to 2009 and Nickelback singer Chad Kroeger from 2013 to 2015. She’s also been linked to actor Wilmer Valderrama and Brody Jenner.

Here’s a look back at Avril Lavigne’s dating history.

Jesse Colburn

Lavigne dated Jesse Colburn, a guitarist in her band in the early 2000s. The “Girlfriend” singer told MTV News in 2004 that Colburn had also left the band after their breakup. “He just wanted to go do his own thing and stuff, and I mean, that happens,” she shared.

Deryck Whibley

Lavigne and Deryck Whibley dated for about one year before getting engaged in Venice, Italy, in June 2005. 13 months later, the couple wed in a private ceremony in California.

After three years of marriage, the Canadian rockers split in September 2009 and Lavigne filed for divorce one month later. She shared in a statement on her website at the time of their breakup, “Deryck and I have been together for 6-and-a-half years. 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.”

She added: “I admire Deryck and have a great amount of respect for him. He is the most amazing person I know and I love him with all my heart. Deryck and I are separating and moving forward on a positive note.”

Whibley also shared a message on Sum 41’s MySpace page, writing, “The past 6 and a half years have been the most amazing years of my life. It’s sad it has come to an end but Avril and I are still family and moving forward in the most positive way possible. Our decision to part ways is amicable and she holds a special place in my heart and forever will be a great and amazing friend. Thanks to all our family, friends and fans for all the support.”

At the time, a source told PEOPLE that Lavigne “married too young and she finally realized that. Avril realized she needs her own life and needs to explore things without him.”

Despite their divorce, the couple remained friends and continued to work together. Lavigne told Ryan Seacrest on his KIIS radio show in January 2010, “He’s one of my best friends … We’ve been friends for a really long time, and we always will be. We’re family and we have a connection.”

In June 2024, the exes performed together during Lavigne’s Greatest Hits Tour stop at the MGM Grand in Las Vegas. They sang Sum 41’s hit song “In Too Deep” for the roaring crowd.

Brandon Davis

Before news of her divorce from Whibley, Lavigne was rumored to be dating Brandon Davis in September 2009.

“She and Brandon Davis have a good time together,” a source told PEOPLE then.

However, another insider said at the time there was “no romance” between Lavigne and Davis at the time of her separation from Whibley.

Wilmer Valderrama

Lavigne was rumored to be dating actor Wilmer Valderrama in November 2009. The pair were spotted at Los Angeles hotspot Wonderland that month and a source told PEOPLE at the time, “There were others at the table, but you could tell they only had eyes for each other. They were whispering close the entire night, laughing and having a lot of fun.”

A source added, “They’ve been friends for a long time and have worked together before.”

Brody Jenner

The singer and reality star Brody Jenner were first linked in April 2010 after they were seen kissing in Las Vegas. A source told PEOPLE the two were “all over each other at a nightclub.”

The following October, Lavigne and Jenner were spotted partying at a club in Hollywood near Lavigne’s ex-husband Whibley. In November 2011, the couple were involved in a bar fight, where they both sustained injuries.

By January 2012, however, Jenner and Lavigne split but remained friendly. The same month, both the musician and the reality star proved there was no bad blood between them on Twitter.

“It really upsets me to read all the FALSE!! stories,” Jenner tweeted. “Avril has always been there for me and is the closest person to my heart. I love her.” Lavigne then replied, “Luv u 2!!! @brodyjenner.”

Chad Kroeger

Lavigne and Nickelback musician Chad Kroeger had a six-month courtship before they got engaged in August 2012. The couple initially met in February 2012 when they collaborated on a song for Lavigne’s fifth studio album, but officially started dating on July 1.

Kroeger popped the question to Lavigne with a 14-carat diamond ring and the singer later opened up about the proposal to Seacrest. “I had been making this scrapbook of my time in the studio. I walk over and he had taken a photo of himself holding the ring box and put the Polaroid in my scrapbook,” Lavigne explained. “Because I had stickers everywhere he put in ‘Will you marry me?’ It was really romantic and kind of made sense.”

The couple married on July 1, 2013, in the South of France. Kroeger told PEOPLE following the nuptials, “We think it’s very cool that our anniversary will always be on Canada Day. We can’t wait to start our life together.”

About three months into the marriage, the Nickelback bandmate shared that Lavigne was an “amazing cook” with ET Canada, adding that “married life’s good. It’s been 94 days. I could give you, like, to the hour if needed.”

Lavigne and Kroeger ultimately split in September 2015 after two years of marriage. Lavigne shared on Instagram, “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. To all our family, friends and fans, thank you sincerely for the support.”

The former couple remained friends and reunited in the recording studio in March 2016, and performed on stage together in September 2017.

J.R. Rotem

The “My Happy Ending” singer and music producer J.R. Rotem were first linked in August 2017 after Rotem posted a pic of the pair on Instagram working together. The couple were also seen holding hands in October 2017. Though they never officially announced their breakup, the duo were not seen together after their fall 2017 outing.

Phillip Sarofim

Lavigne and Phillip Sarofim, the son of Egyptian-American billionaire Fayez Sarofim, were spotted at dinner together in March 2018 in Los Angeles and were seen holding hands the next month.

E! News reported that the couple met “through friends at a dinner party and hit it off.” Lavigne and Sarofim went on another dinner date in May 2018, but by November 2019, they had broken up.

Pete Jonas

She briefly dated indie musician Pete Jonas in 2020. They made their relationship red carpet official when they attended Clive Davis’ annual pre-Grammy gala together in January 2020. However, it’s unclear when the couple parted ways.

Mod Sun

Lavigne and musician Mod Sun (whose real name is Derek Smith) first met when they worked together on her album Love Sux in January 2021.

“I knew we had a very strong unstoppable connection from the first week of writing and working together in the studio. Immediately,” Lavigne told PEOPLE. “He made every day better. It was like I had known him forever. As time went on, things kept getting better, and it felt incredibly natural.”

The couple went Instagram official in September 2021 and made their red carpet debut the same month.

Sun proposed to Lavigne on March 27, 2022, in Paris after just over a year of dating. “It was the most perfect, romantic proposal I could ever ask for. We were in Paris on a boat in the Seine River. We had a violin player, champagne and roses. It felt like time stood still, and it was just the two of us in the moment,” Lavigne exclusively told PEOPLE.

Following their engagement, the couple threw an engagement party.

Nearly a year after the proposal, Lavigne and Mod Sun called off their engagement. A source close to the couple told PEOPLE in February 2023, “Avril and Mod Sun have been on and off for the past two months, but are no longer together as a couple.”

A few days prior to the breakup announcement, Lavigne was seen dining with rapper Tyga at Nobu. However, the insider said, “Avril and Tyga are genuinely friends and nothing more. There was absolutely no third party involved in the split.”

On Feb. 21, 2023, a rep for Sun told PEOPLE: “They were together and engaged as of three days ago when Mod left for tour so if anything has changed that’s news to him. Mod will be performing tonight in Portland at The Hawthorne Theater.”

Tyga

Lavigne and Tyga were first spotted together on Feb. 19, 2023. The pair had dinner at Nobu in Los Angeles one day before the “Girlfriend” singer called off her engagement to Mod Sun.

Then, on March 1, Lavigne and the rapper were seen arriving together for Leonardo DiCaprio’s party at Kùkù in Paris. A few days later, the couple were photographed kissing outside another Paris Fashion Week party.

“Tyga and Avril are getting to know each other,” a source told PEOPLE at the time. “It’s very new. It’s very casual.”

A few weeks later, a source informed PEOPLE that Lavigne and Tyga were “very into each other” and “spending a lot of time together.”

The insider added: “They’re still not exclusive. They’re taking things very slowly to be on the safe side … really [getting] to know each other before diving into something serious.”

In June 2023, the pair called it quits after just three-and-a-half months of dating. A month later, Lavigne and Tyga reunited in Las Vegas before breaking up again a few months later. A source told PEOPLE in October 2023 that the couple are “totally done.”