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Despite knowing each other since they were 11 years old, the pair went off to embark on their respective careers before reconnecting in 2015. Their first date? Taylor Swift's Fourth of July party in Rhode Island. "I went on tour again, and then I went to Taylor's 4th of July party," he told People. "I was texting [Seaborn], and she was like, 'I'm in Rhode Island at a 4th of July party,' and I was like, 'So am I.' I kinda said to Taylor, 'Can I invite one of my old schoolmates?' The rest is history." He also sang about the moment in Taylor Swift's "End Game," too.