It was last year on Aug. 31, 2022 that the Canadian pop star Avril Lavigne was honored with a star on the Hollywood Walk of Fame thanks to her two decade-long career which produced a string of hits, making her one of the most popular artists of all time.

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With fame and stardom defining her career, the 38-year-old songstress is also known for her history of tumultuous affairs, which includes a couple of relationships and two failed marriages. Yes, the “Complicated” singer has been married twice and each ended in divorce.

She married the Sum 41 frontman Deryck Whibley in 2006. Their relationship lasted for four years till they divorced in 2010. Three years later, in 2013, she married the musician Chad Kroeger. The same year, the pair also starred in the music video for “Let me Go,” which was released on Oct. 15.

Unfortunately, their marriage didn’t last long and the couple went on to divorce after two years in 2015. Reflecting on her marriages, Lavigne told Billboard in 2018, “I love love. The way I look at it is, I married my long-term.” But the pop star wasn’t going to give up on love, and in April 2022 she got engaged to singer Mod Sun.

However, a few days back, a source told People that the couple is “no longer together.” The very recent breakup has sparked curiosity in the singer’s past loves. Here’s the lineup.

Deryck Whibley

Lavigne’s very first relationship that attracted popular and tabloid attention was with Deryck Whibley, who she married in 2006. She met him for the first time at a bar at the age of 17 and as per Lavigne’s account, it was quite a memorable experience. “I made out with him the first day I met him. He gave me my first shot of Jäger. I had a tie on—it was back in the days of the tie,” she said to Rolling Stone later in 2011.

The “Girlfriend” singer even displayed her love for Whibley by tattooing a pink heart on her body that surrounded the letter D. The duo married after two years of dating in 2006 but decided to separate in 2009.

The reason is uncertain but a source closer to them mentioned that they had been “growing apart for months” and toward the end acted more like business partners than a married couple. It was also mentioned that Lavigne had “married too young and she finally realized that.”

Speaking on the subject, Lavigne shared a retrospective reflection on her relationship with Deryck. She wrote,

“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. 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.”

After the divorce, they have maintained a cordial relationship and remained friends for many years.

Brody Jenner

Lavigne and The Hills star Brody Jenner officially announced their relationship in early 2010, a few months after she separated from her ex-husband Deryck. They were reportedly spotted kissing in Las Vegas and per a source, were “all over each other at a nightclub.”

Things seemed to getting more serious when in July of the same year, Jenner exhibited a tattoo of Avril on his arm. A month later, she reciprocated by showing off her tattoo containing Brody’s name on her torso.

Throughout their relationship, the couple faced quite a lot of ups and downs, including sustaining severe injuries due to a bar fight, as reported in Nov. 2011. Unfortunately, the couple called it quits in Jan. 2012.

Lavigne’s rising fame was believed to be one of the reasons. Talking to Us Weekly, a source said, “He told her he was tired of always being her plus-one, and always going on tour with her.”

“Brody said, ‘I need to stay in L.A. and get back into TV. Either scripted or reality. But I feel like a loser,’” said a source. The two went their separate ways and were never again seen together. Brody married Kaitlynn Carter in 2018 but got divorced a year later.

Chad Kroeger

Lavigne and Kroeger met in Feb. 2013 and after six months of knowing each other they became engaged in August.

The couple tied the knot on July 1, 2013. Lavigne was proposed to with a 14-carat diamond ring. Talking about her proposal to Ryan Seacrest, the “When You’re Gone” singer said,

“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. Because I had stickers everywhere he put in ‘Will you marry me?’ It was really romantic and kind of made sense.”

Two years later, in Sept. 2015, the couple announced their separation. Lavigne took to Instagram to announce her split from Kroeger where she 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. To all our family, friends and fans, thank you sincerely for the support.”

They remained good friends and even collaborated on various musical projects, including performing together on stage in Sept. 2017.

J.R. Rotem

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Rumors about Lavigne and Rotem started when the duo was spotted holding hands in 2017 after coming out of what seemed to be a romantic dinner. In August of the same year, they shared each other’s pictures on Instagram with Rotem writing “Putting in that work” as the caption. However, their relationship lasted only a month and they were not seen together ever again.

Philip Sarofim

Lavigne met Philip Sarofim, the son of billionaire Fayez Sarofilm at a friend’s party in 2018. Later, the duo was spotted going on dinners and holding hands. They officially announced their relationship in Feb. 2018. However, by Nov. 2019, they broke up and have never been seen together again.

Pete Jonas

In 2020, it was confirmed that the “Let Me Go” singer was dating the Indie musician Pete Jonas. They were seen stepping out of the pre-Grammy party together in Jan. 2020. However, it is unknown how they met or when they broke up as neither party commented on their relationship.

Mod Sun

It seemed like the pop star finally found the one she was looking for. In 2021, she met Mod Sun (whose real name is Derek Smith) while working on solo song “Flames.” Lavigne told People how meeting Sun was a refreshing experience. Speaking on the subject, she said,

“I was getting out of a big relationship, and 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— it. Life’s short.’ I’m a Libra. I love love.”

They officially announced their relationship in Sept. 2021 after appearing together on the red carpet. One thing led to another and on March 27, 2022, Sun proposed to Lavigne with a dazzling designer heart-shaped diamond ring on which she commented,

“It has the words ‘Hi Icon’ engraved in it, which were the first words he ever said to me. And it has Mod + Avril on the inside. He knew from the very beginning I wanted a heart-shaped diamond because on the day we met, we had matching heart-shaped paved rings on. We’ve worn them every day since, so it’s only fitting to have a heart-shaped engagement ring. I love it so much.”

About the proposal, she said,

“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.”

However, almost a year later in Feb. 2023, the couple reportedly called off their engagement. The reason hasn’t been specified yet except that the pair was in an on-again-off-again relationship for the past two months.

The couple seems to be doing their own thing for now. But fans will definitely keep their eyes peeled for any updates about the duo.