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It\u2019s complicated! Avril Lavigne<\/strong><\/a> has endured her fair share of relationship woes over the years, including two divorces.<\/p>\n \u201cI love love,\u201d the \u201cSk8er Boi\u201d singer told Billboard<\/em><\/a> in October 2018 when reflecting on her marriages<\/a>. \u201cThe way I look at it is, I married my long-terms.\u201d<\/p>\n Lavigne met her first husband, Sum 41 frontman Deryck Whibley<\/strong><\/a>, at a bar when she was 17.<\/p>\n \u201cI made out with him the first day I met him<\/a>,\u201d the pop punk star told Rolling Stone<\/em> <\/a>of Whibley in April 2011. \u201cHe gave me my first shot of J\u00e4ger. I had a tie on. It was back in the days of the tie.\u201d<\/a><\/p>\n The pair didn\u2019t begin dating, however, until two years after their first meeting. In July 2006, they exchanged vows at a private estate in Montecito, California. Although the union didn\u2019t last \u2014 Lavigne filed for divorce in October 2009<\/a> \u2014 the exes remained on good terms.<\/p>\n \u201cWe 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<\/a>,\u201d the Grammy nominee wrote in a statement shared via her website, announcing the separation.<\/p>\n Nearly a decade later, the \u201cComplicated\u201d songwriter told Billboard<\/em> of Whibley in 2018: \u201cHe\u2019s a good Canadian guy.\u201d<\/p>\n Lavigne moved on with Brody Jenner<\/strong><\/a>, dating the Hills<\/em> alum<\/a> from 2010 to 2012. After news of their split made headlines, the reality TV personality took to social media to deny speculation that there was bad blood between him and the \u201cGirlfriend\u201d singer.<\/p>\n \u201cAvril has always been there for me and is the closest person to my heart<\/a>. I love her,\u201d Jenner wrote via Twitter in January 2012. Lavigne responded, \u201cLuv u 2!!! @brodyjenner.\u201d<\/p>\n Shortly after the Canada native parted ways with Jenner, she sparked a whirlwind romance with Nickelback lead singer Chad Kroeger<\/strong><\/a>. The duo met in March 2012 while collaborating on Lavigne\u2019s self-titled album. They began dating that July and Kroeger proposed just one month later<\/a>.<\/p>\n The musicians tied the knot in July 2013<\/a>, on their one-year anniversary. After two years of marriage, Lavigne announced via Instagram that they were going their separate ways.<\/p>\n \u201cThrough not only the marriage, but the music as well, we\u2019ve created many unforgettable moments,\u201d she wrote in September 2015. \u201cWe are still, and forever will be, the best of friends, and will always care deeply for each other.<\/a>\u201d<\/p>\n Despite releasing an album titled Love Sux<\/em> in February 2022, the Fast Food Nation<\/em> actress accepted another marriage proposal that March<\/a>, getting engaged to Mod Sun<\/strong><\/a> after about a year of dating.<\/p>\n \u201cThe day we met I knew you were the one,\u201d Mod Sun (real name Derek Ryan Smith) wrote via Instagram at the time. \u201cTogether forever til our days are done.\u201d<\/p>\n Us Weekly<\/em> confirmed in February 2023 that the twosome had called off their engagement<\/a>.<\/p>\n \u201cAvril and Mod Sun have been on and off for the past two months, but are no longer together as a couple<\/a>,\u201d a source exclusively told Us<\/em> at the time. However, Mod Sun\u2019s rep claimed that the pair had been together days prior.<\/p>\n \u201cThey were together and engaged 3 days ago when Mod left for tour so if anything has changed that\u2019s news to him,\u201d his rep told Us<\/em> in a statement.<\/p>\n