Jake Gyllenhaal: The Beginning

Her Age: 20 – 21

Duration of Relationship: October 2010 – January 2011

Similar to her relationship with Mayer, Taylor Swift and Jake Gyllenhaal’s romance was a whirlwind affair that captivated both fans and tabloids alike. Their love story began in the fall of 2010 when they were spotted together at various hotspots in New York City.

Their relationship was marked by outings to coffee shops, walks in Central Park, and cozy dinner dates—typical activities for any couple in the Big Apple. Despite their 10-year age difference, Taylor, then 20, and Jake, 30, seemed to be smitten with each other.