It is unknown when Taylor Swift and Joe Jonas met or when they began dating, however Swift was a regular at Jonas Brothers shows by July 2008, and was often spotted hanging out with Jonas Brother's closest friends at the time, including Demi Lovato.
Although dating rumors were heating up, neither Jonas or Swift confirmed their relationship while they were together. Taylor spoke to People magazine about these rumors just by claiming that, "[Joe]'s an amazing guy and anyone would be lucky to be dating him."
After going on a triple date in August with Nick Jonas, Selena Gomez, Kevin Jonas and Danielle Deleasa, Taylor and Joe were spotted together in public for the first time, at the VMAs in September 7, 2008.
However, by early October, they were no longer in a relationship. In a later interview at Ellen DeGeneres' show, Taylor confirmed that she wrote a song titled "Forever & Always" about Jonas, but stated that he "wasn't in [her] life anymore."
"There's one [song] that is about that guy [Joe], but that guy's not in my life anymore unfortunately." and then threw a shade at Jonas for breaking up with her over the phone in a 27-second phone call. "[...] I'm not even gonna be able to remember the boy who broke up with me over the phone in 25 seconds when I was 18. It was like 27 seconds, that's got to be a record."
Less than two months after his split from Taylor, Joe started dating actress Camilla Belle, who co-starred on Jonas Brother's music video for "Lovebug". His new girlfriend was the main topic on Taylor's later song "Better Than Revenge" from her album "Speak Now" in which she calls out Belle for "stealing" Jonas from her; the song also references Jonas Brother's song "Much Better."
In a less petty song, "Last Kiss," Taylor recalls her relationship with Joe, mourning it and telling listeners that she would "go sit on the floor wearing [his] clothes." and that "[she] doesn't know how to be something that [he] miss."
Over time, Taylor and Joe have apparently resolved their issues and talked it out - or at least, time healed it. They were seen backstage at award shows in 2011, speaking to each other friendly. In a less regretful and more positive tone, Taylor apparently recalled their relationship again in "Holy Ground," a song from her album "Red."
They became close friends in 2015, after Joe started dating one of Taylor's closest friends, model Gigi Hadid. They went out on a double date along with Taylor's then boyfriend, DJ Calvin Harris. Taylor also invited Joe and Nick Jonas to her 4th of July party. Even after Joe and Gigi's later breakup, they seemed to still be friends and on good terms, as they were spotted hugging each other at Coachella in 2016.
In a 2019 appearance at Ellen DeGeneres' show, Taylor recognized that shading Joe publicly at Ellen's show back in 2008 was "too much." "We laugh about it now, but that was mouthy, yeah – some teenage stuff there."
In a later song called "invisible string" from her "folklore" album, Taylor mentioned that she gave "baby presents" to Joe Jonas and his wife Sophie Turner, whom first child, Willa, was born in 2020; "Cold was the steel of my axe to grind/For the boys who broke my heart/Now I send their babies presents."