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Reynolds began dating the "You Oughta Know" singer in 2002, and they became a match made in Canada. They got engaged in 2004 but parted ways three years later. About their split, their reps told People, "They remain close friends and continue to have the utmost love and admiration for each other. They ask that their privacy be respected surrounding this personal matter."
Alanis used their split as inspiration for her "Flavors of Entanglement" album in 2008. The (very touching) song "Torch" was written about Reynolds.
In a 2017 interview with POPSUGAR, Reynolds gave a not-so-subtle callback to his ex-fiancée's hit song by quoting her "Ironic" lyrics, and it was gold.
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