From Joe Jonas to a Quick Fling With Matty Healy, Everyone Taylor Swift Has Dated Through the Years

When: August 2009 — December 2009

After playing boyfriend and girlfriend in the 2010 rom-com "Valentine's Day," these two Taylors started dating for real. Although their relationship earned one of Hollywood's cutest nicknames, "Taylor Squared," a source close to the then-country singer told People, "They went out on a few dates and realized this was just not going anywhere." The sad song "Back to December" off of Swift's "Speak Now" album is reportedly about the "Twilight" star, which expresses regret for how she ended things with him and has lyrics referencing his "tan skin" and "sweet smile."