The song Tim McGraw was inspired by an ex-boyfriend named Brandon Borello. Their relationship ended because he had to go to college. Taylor told USA Today, “He bought the album [Taylor Swift] and said he really loved it, which is sweet. His current girlfriend isn’t too pleased with it, though.” It was named after a musician whose songs she liked. He was going away to college so she wanted to write him something to remember her by.
Picture to Burn was written about an ex-boyfriend named Jordan Alford, whom she calls a redneck, and says he never let her drive his pick-up truck.
Teardrops on My Guitar was written about a boy she liked, whom she never actually dated. “Drew was a real person!” she tells. Drew was surprised when he heard his name in the song. “I never knew she liked me” Drew says. Taylor stated that two years after the song came out Drew showed up at her house and asked her on a date. She declined. “It was the perfect fairytale ending but a little too late.”
Should’ve Said No was about an ex-boyfriend that cheated on her. The boyfriend’s name was Sam Armstrong, and, in the CD booklet, every S, A, and M was capitalized if it was in the correct order.
Joe Jonas broke up with her over the phone, which is something she has complained about on Ellen DeGeneres’ Show and elsewhere. She got her record company to let her record a song about it, to add at the last minute to her album. Forever & Always is the name of that song. She also wrote Last Kiss about him and Better than Revenge is about his ex-girlfriend, Camila Belle.
Taylor Lautner became her boyfriend after they met on set for the film Valentine’s Day. Their relationship was popularly known as Taylor Squared. They broke up in early 2010. She mentioned going to a hockey game with him during her October 29th 2009 appearance on The Ellen Show. According to MTV he was more into her than she was into him, he going everywhere he could to see her, but it was not working out.  They have apparently decided to just be friends.
The song, Back to December is suspected to be about Taylor Lautner. The song is an apology to him. Some of the lyrics go…” Your guard is up and I know why. Because the last time you saw me is still burned in the back of your mind …you gave me roses and I left them there to die. So this is me swallowing my pride, standing in front of you saying I’m sorry for that night.
And I go back to December all the time. You gave me all your love and all I gave you was goodbye.” At the end of the song she asks for his forgiveness and hints to the fact she wants to be with him again. The couple hasn’t reunited and at the recent American Music Awards Swift performed the song and at the end added “and he said..it’s too late to ‘pologize” from popular song “Apologize” by the band One Republic. She is alluding to the parody video Taylor Lautner made for “Apologize”.  Time magazine listed this is one of the top apologies of 2010. 
Jake Gyllenhaal reported spent $160,000 to have her flown over on a private jet for a date.  He later broke up with her through text. 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 him.
The songs Dear John and I Knew You Were Trouble are rumored to be about her ex-boyfriend John Mayer, whom she dated briefly after collaborating with him on a song.
The song Enchanted is about Adam Young of Owl City but she never dated him, although he did state his interest in her. 
Out of the Woods and Style are supposedly about ex-boyfriend Harry Styles. In turn, the One Direction song Perfect is rumoured to be inspired by Styles’ romance with Swift.
Conor Kennedy is rumored to have inspired the song Begin Again.
To learn about Taylor’s current boyfriend, please read Current love interest.