Taylor Swift is an award-winning singer-songwriter who is famous for her song lyrics based on her real-life experiences. Swift first entered the music scene as a teen country singer and captured the attention of many through her debut single, Teardrops on My Guitar. Through the years, Swift has garnered numerous awards and recognitions. Among are her multiple wins of Album of the Year in Grammy Awards and 32 wins in American Music Awards.

Swift has achieved a fine credit score ever since she became the recipient of 28 Guinness World Records and became a part of the 100 Greatest Songwriters of All Time. However, her dating life became as famous as her songs as Taylor got involved with several high-profile relationships over the past decade. In 2020, Taylor Swift appeared to have patched things up and amend her rifts against music giants. It also seems like the wide-eyed girl from Pennsylvania has finally found the man worth writing love songs about. However, let us revisit her infamous dating list and the song she dedicated to each of her past lovers.

Joe Jonas (July – October 2008) – Last Kiss & Forever and Always

Taylor’s first-ever high-profile romance was with the Jonas Brothers singer, Joe Jonas. The two were spotted together on several occasions, but their relationship did not last.

Sometime in October, Joe made his infamous 27-seconds break-up call to Taylor. In return, Taylor wrote the songs Last Kiss and Forever and Always dedicated to her relationship with Joe. The song, Better Than Revenge, was also rumored to be about Joe Jonas’s new girlfriend, Camilla Belle. Dropping clues on the songs such as “she’s an actress,” positioning Camille on the credits.

Lucas Till (March – April 2009) – You Belong With Me


Lucas Till and Taylor Swift met at the set of the You Belong With Me music video. The young actor and Taylor seem to have a good time together and started dating. The two went separate ways after just a month of dating. According to Till, they both decided to part ways as they seem to have no spark together. Although Lucas did not take credit for any Taylor songs, You Belong With Me probably reminds her about Lucas.

Taylor Lautner (August – December 2009) – Back to December


Taylor Lautner and Taylor Swift met on Valentine’s Day, where they starred as a young couple. The two turned their relationship into reality and started dating in August of 2009. Unfortunately, the Taylor duo confirmed their split in December 2009. When the single, Back to December, was released, many believed that it was about her relationship with Taylor Lautner. Lines that go, “I miss your tan skin, your sweet smile,” hinted that it is Lautner who Taylor is referring to. To this day, fans give Lautner credit for inspiring the pop ballad.

John Mayer (December 2009 – February 2010) – Dear John


By the end of 2009, just when Taylor broke up with Taylor Lautner, she began dating John Mayer. The two got to know each other after collaborating on the song Half of My Heart. Because of their age difference and John’s notorious dating background, the couple’s relationship received a considerable degree of backlash. As such, their relationship did not last as it ended in February 2010. Taylor released the Speak Now album in October of 2010. A track titled Dear John was in it, obviously pointing to her relationship with the singer.

Jake Gyllenhaal (October 2010 – January 2011) – The Last Time and All Too Well 


In 2012, Taylor Swift released her Red album. It was no surprise that it is mostly about relationships and heartbreaks, starting with The Last Time and All Too Well. These songs are said about her three-month romance with Jake Gyllenhaal.

The two started dating in October despite their ten-year age gap. When Jake broke up with Taylor in January 2011, Taylor was left devastated and inspired to make songs that tell her story with Jake. So the song All Too Well was born, giving credit to the brief romance the two shared.

Connor Kennedy (July – October 2012) – Begin Again

Connor and Taylor began dating in July of 2012 until October of the same year. The song Begin Again – the last track of the Red album, was intended for Connor. Fans based it on their relationship timeline that overlaps with the conclusion of Red. As Taylor was no stranger to dating older men, here comes Connor Kennedy breaking Taylor’s streak. Notably, the grandson of Robert F. Kennedy was four years younger than Taylor, who was 22 at that time. Again, Taylor received a certain degree of judgment for her relationship with the young Kennedy.

Harry Styles (2012 – January 2013) – Style, I Knew You Were Trouble, and Out of the Woods 

Taylor’s time with Harry Styles was one of the most intense relationships she ever had. The two sporadically dated in 2012 and announced their first break up in April 2012. Taylor later tweeted, “til you put me down” – a line from her song I Knew You Were Trouble. However, the two got back together in December of 2012 and broke up again in January 2013. Within that short period, the two share a degree of intimate moments. On her 1989 album, Style was obviously about Harry Styles, and the song Out of The Woods seems to be the break-up song of Taylor with Harry.

Calvin Harris (February 2015 – June 2016) – Look What You Made Me Do


Ellie Goulding takes credit for introducing Taylor to her next lover, Calvin Harris. Interestingly, Calvin was the longest relationship Taylor had. Still, as they say, all things must come to an end, and the two went their separate ways after 15 months together. At first, it seems like a mutual decision, but in two weeks, all hell broke loose for Calvin when Taylor was spotted getting cozy with another man. Taylor fought back, and out came the song Look What You Made Me Do. 

Tom Hiddleston (June – September 2016) – Look What You Made Me Do


Tom Hiddleston was the man Taylor Swift was with two weeks after her break up with Calvin Harris. Although Taylor claims no cheating ever happened, Calvin thought otherwise. When Tom and Taylor went public, they gathered mixed reactions among their fans. Tom’s fans shout “Loki, NO!” mimicking Thor’s infamous voice, and Taylor’s fans thought he is too good to be true. But like her previous relationships, Taylor got off their love wagon after three months together. In the music video of Look What You Made Me Do, some dancers wore the same shirt that Tom had worn in the past, implying that the song is also for Tom. Well, at least Tom can take credit for some Taylor Swift masterpieces.


Taylor Swift went stealth mode after her infamous feud with Kanye West in 2016. Because of this, her dating life was hidden from the public. However, in 2017, a photo of Taylor and Joe Alwyn spread across the media. Apparently, the two have been dating since late 2016. As of today, Taylor and Joe are still together. During the 2020 Grammy Awards, Taylor mentioned and gave Joe credit for helping her write the songs in her Folklore album and keeping her company during quarantine. As such, Taylor must have written the song Lover from her Lover album in 2019. The clues are in the lines, “I’ve loved you three summers now, honey, but I want ‘em all.” Well, we really do wish Taylor Swift all the best in her relationship!