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Love is in the Stars: Taylor Swift Relationship Timeline

Jul 17, 2018

Country cutie Taylor Swift has had her share of suitors over the years, and the 22-year-old singer has never had a problem channeling her heartbreak into her music, but sometimes it's a challenge to keep up with her busy love life, find out more in our Taylor Swift Relationship Timeline!

Taylor Swift Relationship TimelineLike her music videos, Taylor is looking for fairytale ending
 

Drew Who?

When Taylor first burst onto the music scene she called out a friend named Drew in the song "Teardrops on My Guitar," asking why he he was interested in another girl when she was right before her eyes, after that though Taylor quickly moved into the celebrity dating circle and was careful to not names names anymore.

Jonesin' for a Jonas

Taylor Swift and Joe JonasTaylor Swift and Joe Jonas met in 2008
 

In 2008 it was rumored that the blonde beauty was dating none other than Joe Jonas, and while both he and Taylor danced around the topic, she told MTV News that summer that, "he's an amazing guy, and anyone would be lucky to be dating him."

We're not so sure she felt that way after he left her to hook up with his "Lovebug" video co-star Camilla Bell, and Taylor admitted to penning the song 'Forever and Always" about the relationship, confessing "I addressed it, and, you know, that's a chapter in my life that's closed now."

Love for Lautner

Taylor Swift and Taylor LautnerThe two Taylors called it quits in 2009
 

From Joe Taylor she moved on to quietly having a fling with her "You Belong With Me" co-star Lucas Till, but it wasn't found out until it had ended and she had started seeing Hollywood heartthrob Taylor Lautner. Lucas said of his time with Taylor  "We just really both liked each other, [but] most relationships work out 'cause you get along and then you don't, and then you make up and it's passionate. And with us I really just liked her as a friend. That's the only reason that didn't work out." 

Taylor met her "Valentine's Day" co-star Taylor Lautner in the summer of 2009, and I think it's safe to say that it was probably more passionate, although the two never admitted to being together they were often spotted that year out holding hands. Things had ended by December 2009, but in the fall of the next the lovestuck singer admitted that she still had a crush on him. "Taylor Lautner. It's always going to be Taylor." 

Mayer Madness

John Mayer and Taylor SwiftRumor has it her song "Dear John" is about Mayer
 

As always Taylor never admitted officially to dating fellow musician John Mayer in 2010, but it didn't seem to be much of a secret either and the story goes that song "Dear John" is all about him (not exactly a stretch.) That same year gossip hounds also speculated that she dated Glee star Cory Monteith and her "Mine" co-star Toby Hemingway. We'll never know for sure though! When asked about her bounty of beaus she said "I write in great detail about my personal life, but I don't talk about it."

Jake the Mistake

Jake Gyllenhaal and Taylor SwiftJake Gyllenhaal and Taylor dated in late 2010
 

Perhaps her biggest heartbreak to date, Taylor's romance with leading man Jake Gyllenhaal in 2010 caused the most buzz in the press because they were so gosh-darned cute together (despite the age difference), the romance was short-lived and neither one spoke to the press about it, although they were publicly very affectionate. Although they broke up at the end of that year, they were still spotted together a few times in early 2011.

Kennedy Crush

Taylor Swift and Conor KennedyTaylor is currently with Conor Kennedy
 

Taylor's newest conquest is practically American royalty, and in a drastic change for Taylor she's dating a younger man! At just 18-years-old Conor Kennedy seems to have won Taylor's heart over the course of the summer, and she apparently gets full approval from the rest of the Kennedy clan.

There are currently rumors that Conor isn't the only family member to take an interest in Taylor, rumors are circulating that Conor's cousin Patrick Schwarzenegger may have locked lips with long-locked singer earlier in the summer as well.

Taylor has just one thing to say to all the guys who've ditched her over the years...We are never ever,ever getting back together! Check out the song below.

 

Have Your Say

Who do you think was the best match for Taylor? Let us know in the comments section below!