Taylor Swift’s Breakup Songs & Relationships

Author: Julia Zoe

Looks like music sensation Taylor Swift has everything going for her … except when it comes to the men in her life, the poor girl can’t seem to hang onto any. The phenomenal singer might have multiplatinum status, more than a dozen prestigious awards under her belt but when it comes to her love live she hasn’t had much luck.

Swift has had her share of suitors over the years and has dated men older than her, younger than her, actors, musicians and even political offspring’s, you name it. She has proven to her fans that she is not an ageist and has dated everyone from an 18 year old Connor Kennedy to 35 year old rocker John Mayer. Swift doesn’t discriminate as well and her dating past includes men from different nationalities.

Her relationships receive frequent media attention and could be one reason why Taylor Swift Tickets are always in high demand. The talented songwriter has used her relationships to her advantage and has written heartfelt lyrics to some her most popular songs.

Here’s a look at the men who inspired those brilliant singles:

Joe Jonas

Joe Jonas


It all began with The Jonas Brothers frontman Joe Jonas. The romance was age appropriate and occurred when Taylor had just arrived onto the music scene while Joe and his brothers were on top of their game.

Reportedly Jonas left Swift after a couple of months for his “Lovebug” video co-star Camilla Belle.

Breakup song to come out: Forever & Always.






Taylor Lautner

Taylor Lautner


Technically Taylor Swift’s and Taylor Lautner’s 2009 romance was illegal in many states as she was dating a minor at the time. The two met on the sets of chick flick Valentine’s Day and started spending a lot of time together. However, both young stars denied having a relationship.

In a tweet Taylor Swift admitted on having a crush on the other Taylor. She wrote, “Taylor Lautner. It’s always going to be Taylor.

Breakup song to come out: Back to December.




John Mayer

John Mayer



Swift went seriously wrong when she started seeing rocker John Mayer. Mayer who is 11 years older than Swift was a famous playboy left Swift heartbroken as he has done with many young Hollywood starlets.

Breakup song to come out: Dear John.







Jake Gyllenhaal

Jake Gyllenhaal


Taylor Swift went all out when she started dating the Prince of Persia star Jake Gyllenhaal. The usually shy Swift was seen all around town with Gyllenhaal during Thanksgiving and if rumors are to be believed the couple met each other’s families too. However, it did not end well and Gyllenhaal called it quits.

Breakup song to come out: All Too Well.






Connor Kennedy

Connor Kennedy



After suffering heartbreak at the hands of two older men, Swift decided to date someone younger than her for a change. In comes Connor Kennedy. Now everyone knows offspring’s of the fabled political family are practically royalty and that might’ve caught Swift’s eye. The two started dating while Connor was still in high school and ironically it ended when Connor had to return to high school later that fall.

Breakup song to come out: Everything Has Changed.





Harry Styles

Harry Styles



After her breakup from Connor, it was Harry Styles who gave Swift a shoulder to cry on. The friendship quickly turned to romance and the two spent Taylor’s 23rd birthday together in a rural town in Northern England.


As of today Swift’s romance with One Direction frontman is going strong. Here’s hoping the romance lasts and heads for a happily ever after which is a rarity in Hollywood.

Swift’s dating history has had little effect on her phenomenal career. This icon of Country music continues to sell millions of records worldwide. This Country rocker knows how to give her fans a rock show and watching her perform live is highly recommended.


  1. melissa says:

    Harry’s been ever the gentleman throughout this whole fake relationship.

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