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List of Taylor Swift’s Ex-Boyfriends and the Songs Behind Them

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Taylor Swift is not shy about the fact she writes songs about her ex-boyfriends. You can’t really blame her since most country songs are written about real life experiences and Taylor’s just happen to be dating at this point in her life.

You can’t tell me that some of Kelly Clarkson’s songs or Reba’s songs aren’t about ex-boyfriends/ex-husbands. Now they may not be as public about calling them out like Taylor Swift has been, but they still have meaning.

I guess I didn’t realize how many ex-boyfriends Taylor had but here’s the current list of Ex’s and the rumored songs that came from her different relationships.


1.)Brandon Borello
The song “Tim McGraw” was inspired by Brandon. Their relationship ended because he had to go to college. She wrote the song to remember him, and it was her first single to chart on radio.

2.) Sam Armstrong
Should’ve Said No was about an ex-boyfriend that cheated on her. The boyfriend’s name Sam was in the CD booklet and every S, A, and M was capitalized if it was in the correct order. Ya think he made a bad choice, YEP!

3.) Joe Jonas
He broke up with her over the phone, which is something she has complained about on Ellen Degeneres’ show and elsewhere. She wrote a couple of album cuts about him, one called “Forever & Always.”

4.) Taylor Lautner
Taylor became her boyfriend after they met on set for their film Valentine’s Day. The relationship was popularly known as Taylor Squared. They broke up in early 2010 and her song “Back to December” is about him. Sounds like she may have screwed this relationship up. Oh well, he’s Taylor Lautner.

5.) Jake Gyllenhaal
Jake reportedly spent $160,000 to have her flown over on a private jet for a date. He was seen with his sister Maggie Gyllenhaal quite a bit. He later broke up with her via text message. The songs We Are Never Ever Getting Back Together, State of Grace, All Too Well, Girl at Home and The Moment I Knew are rumored to be about JG.

6.) John Mayer
The songs Dear John and I Knew You Were Trouble are rumored to be about ex-boyfriend John Mayer, whom she had a fling with at one time. He’s now happily living with Katy Perry.

7.) Conner Kennedy
Taylor and Conner dated about 3 months and got considerable press for crashing one his family members wedding. The song “Begin Again” off the a;bum, RED is rumored to be about the Kennedy son.

8.) Harry Styles
The One Direction pop singer had a short lived relationship that ended with Taylor leaving a vaction on a yacht by herself. She took a jab at him when she opened the grammy’s with “We are never ever getting back together.” She used a british accent during the song implying it was a stab at Harry.

9.) ???? Who know’s …at this point Taylor says shes taking a break from dating. We will keep you posted if that changes.

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