21. Taylor Swift and Jake Gyllenhaal
This is a very short but sweet romance that was initiated through none other than Gwyneth Paltrow. The “Shakespeare in Love” Oscar winner introduced the two to each other at her London home.
As said, it was a short-lived romance and since Taylor loves to write about her relationships, it is rumored that their break up is the inspiration for her two songs: “All Too Well” and the catchy “We Are Never Ever Getting Back Together.”