Taylor Swift lyrics used as pick-up lines - video
The 22-year-old spent the day approaching women in Nashville and trying to impress them with lines from Swift's most famous songs - complete with hidden camera.
Wooldridge tried out lines such as, "You're the reason for the teardrops on my guitar", "Marry me, Juliet, you'll never have to be alone", and, "I knew you were trouble when you walked in".
However, while the 'Love Story' singer's tracks may be hits in the charts, they fared less well when used to score a date.
"As soon as I moved here basically, I fell in love with Taylor Swift, because she seems super awesome and funny and sweet," Wooldridge told the Tennessean.
"For this video, I decided I want to meet a girl that's like Taylor Swift - sweet and funny - so I figured that a good way to do that would be trying to pick them up with Taylor Swift lyrics."
Most of the women seemed flattered, some confused, but he failed get anyone's phone number. After one rejection he belted out 'We Are Never Ever Getting Back Together'.