From Sk8er Boys to Rock Stars: Unveiling Avril Lavigne's Epic Dating Journey

Avril Lavigne has faced numerous challenges in her romantic life, having gone through two divorces. Reflecting on her marriages, the "Sk8er Boi" singer expressed her fondness for love, stating that she considers her ex-partners as long-term companions.

Lavigne encountered her initial spouse, Deryck Whibley, the lead vocalist of Sum 41, at a bar during her adolescence when she was just 17 years old. Recalling their encounter, the pop punk sensation shared with Rolling Stone in April 2011 that they engaged in their first kiss on the very day they met. Additionally, Lavigne reminisced about Whibley offering her a taste of Jägermeister, marking her introduction to the alcoholic beverage. She also mentioned that she was sporting a tie at the time, reflecting the fashion trends of that era.

They didn't start dating until two years after their initial encounter. In July 2006, they got married at a private estate in Montecito, California. Despite the marriage not lasting, with Lavigne filing for divorce in October 2009, the former couple maintained a good relationship.

"We have been friends since I was 17, started dating when I was 19, and got married when I was 21. I am thankful for the time we spent together and I feel grateful and blessed for our continued friendship," stated the Grammy nominee on her website when announcing their separation.

After their breakup became public, Brody Jenner, a reality TV personality, used social media to dispel rumors of any animosity between him and Avril Lavigne, referring to her as the "Girlfriend" singer.

Avril has always been my rock, my closest confidant. She holds a special place in my heart, and I am deeply in love with her," Jenner expressed on Twitter in January 2012. Lavigne reciprocated the affection by responding, "@brodyjenner Luv u 2!!!"

Not long after ending her relationship with Jenner, the Canadian singer ignited a passionate love affair with Chad Kroeger, the lead singer of Nickelback. Their paths crossed in March 2012 while collaborating on Lavigne's self-titled album. The sparks flew, and they officially started dating in July. Surprisingly, only a month later, Kroeger got down on one knee and proposed to Lavigne.

After celebrating their one-year anniversary in July 2013, the musicians decided to part ways after two years of marriage. Lavigne took to Instagram in September 2015 to announce their separation, expressing gratitude for the memorable moments they had created together both in their marriage and through their music. She emphasized that despite their decision to separate, they would always remain the best of friends and hold deep care for each other.

Mod Sun, whose real name is Derek Ryan Smith, expressed his deep affection for the Fast Food Nation actress by declaring, "The day we met, I knew you were the one." This heartfelt message was shared on Instagram, coinciding with their engagement announcement in March, just a year after they started dating. Mod Sun confidently expressed his commitment to their relationship, stating, "Together forever til our days are done."

Avril and Mod Sun ended their engagement in February 2023, according to a source. The insider revealed that they had been experiencing an on-again, off-again relationship for the past two months but are now officially no longer a couple. On the other hand, Mod Sun's representative countered this claim, stating that the two had still been together just days before.

Below is a revised version of fragment 9:

According to his representative, Mod and Lavigne were in a committed relationship until his recent departure for the tour. If there have been any developments since then, Mod is unaware of them.

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Avril Lavigne's Dating History: Deryck Whibley, Brody Jenner, Chad Kroeger, Mod Sun and More

It's complicated! Avril Lavigne has endured her fair share of relationship woes over the years, including two divorces.

"I have a deep affection for love," expressed the "Sk8er Boi" singer when discussing her marriages with Billboard in October 2018. She further added, "The way I perceive it is that I committed myself to long-lasting relationships."

At the tender age of 17, Lavigne encountered her initial spouse, Deryck Whibley, the lead vocalist of Sum 41, while both were at a bar.

The pop punk star revealed to Rolling Stone in April 2011 that she had shared a memorable encounter with Whibley on the first day they met. She fondly recalled him giving her her first shot of Jäger, and noted that it was during a time when she still wore ties. Despite this initial connection, the couple didn't enter into a romantic relationship until two years later. They eventually tied the knot in July 2006 at a private estate in Montecito, California. Although their marriage didn't stand the test of time, with Lavigne filing for divorce in October 2009, the former couple managed to maintain a positive relationship.

"We have been friends since I was 17, started dating when I was 19, and got married when I turned 21. I am thankful for the time we spent together and I feel grateful and blessed for our enduring friendship," the Grammy nominee expressed in a statement shared through her website, informing about the separation.

Almost ten years later, the "Complicated" songwriter described Whibley as a "decent Canadian man" in an interview with Billboard in 2018.

Lavigne then began a new relationship with Brody Jenner, a former cast member of the reality TV show "The Hills," which lasted from 2010 to 2012. When news of their breakup surfaced, Jenner took to social media to address rumors of any animosity between him and the singer.

In a tweet posted in January 2012, Jenner expressed his affection for Lavigne, stating, "Avril has always been there for me and holds a special place in my heart. I love her." Lavigne responded with equal warmth, tweeting back, "Love you too!!! @brodyjenner."

Shortly after ending her relationship with Jenner, the Canadian artist found herself in a passionate love affair with Chad Kroeger, the lead singer of Nickelback. Their paths crossed in March 2012 during their collaboration on Lavigne's self-titled album, and by July of the same year, they were officially dating. Surprisingly, only one month later, Kroeger popped the question and the couple got engaged.

In a beautiful twist of fate, Lavigne and Kroeger exchanged vows in July 2013, precisely on their one-year anniversary. However, after two years of being married, Lavigne took to Instagram to make the heartbreaking announcement that they had decided to go their separate ways.

"We have crafted countless unforgettable moments, not just through our marriage, but also through our shared love for music," she penned in September 2015. "We remain the closest of friends, bound together by a deep and everlasting care for one another."

In spite of unveiling her album titled Love Sux in February 2022, the actress from Fast Food Nation embraced yet another marriage proposal the following March. After approximately a year of dating, she said yes to Mod Sun and they became engaged.

In February 2023, it was confirmed that the couple had ended their engagement, as Mod Sun (real name Derek Ryan Smith) expressed on Instagram, "The day we met, I knew you were the one. Together forever until our days are done."

Avril and Mod Sun's relationship has experienced its ups and downs over the last two months. However, according to an exclusive source, they are no longer together as a couple. Mod Sun's representative, on the other hand, contradicted this statement, asserting that the pair were still together and engaged just three days ago before Mod Sun left for tour. If there have been any changes in their relationship status, it seems to be news to him.

Scroll down for a look at Lavigne’s dating history over the years:

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Deryck Whibley

Lavigne crossed paths with Whibley at the age of 17 and their romantic relationship blossomed two years later. Despite their divorce in 2010 after a four-year union, the Canadian couple managed to maintain a friendship and even joined forces on Lavigne's 2011 album, Goodbye Lullaby.

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Brody Jenner

The singer known for her hit song "What the Hell" was in a relationship with Jenner from 2010 to 2012. After their breakup, both the singer and the DJ took to Twitter to exchange amicable messages, demonstrating that their split was not filled with animosity.

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Chad Kroeger

Lavigne crossed paths with the "Rockstar" singer during the production of her self-titled album in March 2012.

In a 2018 interview with Billboard, the Under My Skin artist reminisced about her initial considerations and decision to collaborate with Kroeger during that period.

"He has a vast collection of chart-topping songs and is skilled at playing the guitar," she expressed enthusiastically. "This has the potential to be a remarkable partnership." Soon after, I found myself wearing a luxurious 14-carat ring on my finger.

After their wedding in July 2013, the songwriters went on to publicly declare their separation in September 2015. Despite the passage of three years, Lavigne continued to speak highly of her former spouse, acknowledging Chad's band's tremendous success of selling over 50 million albums and consistently filling arenas across the globe, as she mentioned to Billboard magazine.

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Phillip Sarofim

The “Head Above Water” singer began dating the son of Texan billionaire Faye Sarofim in February 2018. Us confirmed in November that the duo had called it quits. 

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Mod Sun

Lavigne announced her engagement to Mod Sun after more than a year of dating via Instagram in March 2022. 

"Yes! I love you forever," she wrote alongside pictures showcasing her heart-shaped diamond ring and the romantic proposal that occurred with the Eiffel Tower as the backdrop in Paris.

In February 2023, it was confirmed by Us that the couple had decided to end their engagement. Rumors of Lavigne and her partner from Minnesota parting ways began circulating when the "I'm With You" singer was seen having dinner with Tyga earlier in the same month.

Avril and Tyga are truly just friends, according to an insider who exclusively confirmed to Us. The source clarified that their outing was purely platonic and there was no involvement of any third party in their breakup.

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Tyga

In February 2023, rumors of a romance between the rapper known as "Juicy" and Lavigne began to circulate after they were seen together at a dinner. Initially, a source assured Us that their relationship was purely platonic. However, it was later confirmed by Us that Lavigne and Mod Sun had quietly ended their engagement.

In the weeks that followed, the Canadian singer was seen in Paris with Tyga, which only intensified the speculation about their romance. Finally, in March 2023, the couple publicly acknowledged their relationship when they were caught kissing at a party during Paris Fashion Week. However, just four months later, it was confirmed in June 2023 that the pair had decided to end their romance.

According to an exclusive source, despite the breakup, they have managed to maintain a cordial relationship. The source revealed that they both realized they are better off as friends rather than romantic partners.