Perhaps the breakup that has followed Taylor Swift and Katy Perry longer than any of their exes is the end of their friendship in the 2010s. After becoming industry pals more than a decade ago, a rift over some backup dancers led to a handful of perceived diss tracks, thinly-veiled interview comments, and one common ex-boyfriend.

But 2018 brought a literal olive branch and 2019, an appearance from Perry in Swift’s “You Need to Calm Down” music video. Could 2020 be the year we finally get the long-rumored musical collaboration between them? Ahead, relive Swift and Perry’s longstanding relationship through all of its ups and downs.

September 2008: Swift and Perry were photographed together for the first time, alongside Miley Cyrus, on the 2008 MTV Video Music Awards red carpet. Both singers were on the rise at the time, following the release of Perry’s sophomore album, One of the Boys and two months before Swift’s second album, Fearless.

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February 2009: A few months later, the pair posed together again at a Grammy event honoring Clive Davis in Beverly Hills.

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They sat at the same table as Cyrus during the event on February 7. At the Grammy Awards that year, Perry was nominated for Best Pop Vocal Performance for “I Kissed a Girl.”

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