July 2008

The “Romeo and Juliet” singer had a brief romance with the former Disney Channel star, beginning in July 2008.
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October 2008

Jonas dumped Swift over the phone with a 27-second call in October 2008. The Grammy winner confirmed the breakup details while appearing on the Ellen DeGeneres Show the following month, saying, “It’s all right – I’m cool.” She continued: “You know what, it’s like, when I find that person that is right for me, he’ll be wonderful. When I look at that person, I’m not even going to remember the boy who broke up with me over the phone in 25 seconds when I was 18.” Swift said that after she hung up she checked to see how long the call really was, adding, “I looked at the call long — it was like 27 seconds. That’s got to be a record.” The Jonas Brothers member responded to Swift’s remarks via his MySpace page at the time. “Any time you are in a relationship for any length of time, there are going to be issues. Sometimes they resolve; other times they lead to a change of heart. This was the case recently,” the blog read. “Maybe there were reasons for a breakup. Maybe the heart moved on. Perhaps feelings changed. I am truly saddened that anything would potentially cause [the fans] to think less of me.”
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September 2023

Shortly after Jonas filed for divorce from Turner, Swift was seen hanging out with Turner in NYC twice in one week. Photos of the two women hugging and strolling arm in arm went viral, as Swifties couldn’t help but notice a connection to a lyric from the songwriter’s 2022 song “Vigilante S—t”: “Picture me thick as thieves with your ex-wife.”
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July 2008

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The “Romeo and Juliet” singer had a brief romance with the former Disney Channel star, beginning in July 2008.
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The story of  Taylor Swift and Joe Jonas has had some unexpected twists and turns.

The duo’s messy split made headlines in October 2008. Swift later revealed that Jonas broke up with her during a 27 seccond phone call after three months of dating. She went on to pour her feelings about the Jonas Brothers musician into song, including the Fearless track “Forever and Always” and the Speak Now tune “Better Than Revenge.”

While it once seemed like there was too much bad blood between the exes for them to ever bury the hatchet, Swift and Jonas famously went on a double date with their then-partners Calvin Harris and Gigi Hadid — oh, and Karlie Kloss tagging along as a fifth wheel — in 2015.

Keep scrolling for a look at Swift and Jonas’ ups and downs over the years: