Jake Gyllenhaal: October 2010 - January 2011

Taylor and Jake Gyllenhaal dated in late 2010, with their age gap and intense media attention reportedly putting pressure on the relationship.

They were together for around three months, though the split left a lasting impact on Taylor.

Her Red album, especially the extended version of All Too Well, is widely believed to be inspired by their breakup, including the now-iconic lyric about “a scarf”.