Singers Rank All of Taylor Swift's Exes  

Jessica Lawshe
33.6k votes 4.2k voters 83.7k views 18 items

List Rules Vote up the exes who you think Taylor was the best with.

Taylor Swift is known for her amazing songs, her great voice, and her awesome girl squad. But she may be even more famous for her ever-growing list of song-inspiring exes. Seriously, Taylor Swift's ex-boyfriends could be fuel for many albums to come. We'll just have to wait and see, but in the meantime, we're leaving it up to you to rank all of Taylor Swift's exes! 

It seems our T. Swift is just drawn to heartbreak. And while we love the songs she wrote about her exes, we still want the best for her! We knew that John Mayer was never going to be a good fit for her - hello, he's like "Mr. Heartache." We had hope for Joe Jonas, but shame on him for that 27-second phone call breakup. Then we thought maybe Harry Styles would be a good match. He wasn't, but we're pretty grateful for the songs "Out of the Woods" and "Style" that the One Direction singer inspired.

While Taylor has been romantically linked to a bunch of heartthrobs, including Zac Efron, this list is focused on the guys she actually dated - not just guys she was rumored to be dating. Although, it is pretty hard to keep it all straight! 

It's hard to pick which one of Taylor's exes is the best and which one is the worst, which is why we're tossing this list of Taylor Swift's ex-boyfriends to you. Upvote the Taylor Swift exes that you think she should have stayed with!

list ordered by

1
1,561 1,393
Taylor Lautner is listed (or ranked) 1 on the list Rank All of Taylor Swift's Exes
age 23

Taylor Swift and Taylor Lautner dated from August 2009 to November 2009 after meeting on the set of Valentine’s Day.

2
1,467 1,316
Harry Styles is listed (or ranked) 2 on the list Rank All of Taylor Swift's Exes
age 24

Harry Styles and Taylor Swift were only together from December 2012 to January 2013, but apparently it was enough time to fuel lots of angst-y break-up songs.

3
1,068 920
Tom Hiddleston is listed (or ranked) 3 on the list Rank All of Taylor Swift's Exes
age 37

Swift and Hiddleston - collectively known as Hiddleswift - dated during the summer of 2016. Only "official" for a few short months, E! News reported on their demise in early 2016, quoting a source close to the couple: "Taylor felt he wanted to take the relationship to be too public."

4
1,417 1,269
Jake Gyllenhaal is listed (or ranked) 4 on the list Rank All of Taylor Swift's Exes
age 37

Though the two only dated from October 2010 to January 2011, the songs "We Are Never Getting Back Together" and "The Moment I Knew" are rumored to be about Jake.

5
991 887
Calvin Harris is listed (or ranked) 5 on the list Rank All of Taylor Swift's Exes
age 34 Taylor dated the DJ and producer from March 2015 to June 2016

6
937 1,404
Joe Jonas is listed (or ranked) 6 on the list Rank All of Taylor Swift's Exes
age 28

Joe Jonas allegedly dumped Taylor via a 27-second phone call in October 2008 after the two started dating in July of that same year.

7
638 1,224
Eddie Redmayne is listed (or ranked) 7 on the list Rank All of Taylor Swift's Exes
age 36

Eddie Redmayne and Taylor Swift were rumored to have had a secret relationship for a few months from 2011 to 2012.

8
655 1,294
Lucas Till is listed (or ranked) 8 on the list Rank All of Taylor Swift's Exes
age 27

Taylor dated her "You Belong With Me" music video co-star Lucas Till from March 2009 to April 2009.

9
545 1,174
Chord Overstreet is listed (or ranked) 9 on the list Rank All of Taylor Swift's Exes
age 29

Taylor was linked to Glee star Chord Overstreet for a few months in 2011.

10
618 1,415
John Mayer is listed (or ranked) 10 on the list Rank All of Taylor Swift's Exes
age 40

Taylor was only 19 when she dated John Mayer from November 2009 to February 2010.  He was 32.

11
569 1,300
Cory Monteith is listed (or ranked) 11 on the list Rank All of Taylor Swift's Exes
Died at 31 (1982-2013)

Taylor and the late Glee star allegedly dated in 2010.

12
364 1,154
Conor Kennedy is listed (or ranked) 12 on the list Rank All of Taylor Swift's Exes

Taylor Swift had a summer fling with Conor Kennedy (Robert Kennedy's grandson) from July 2012 to September 2012.

13
332 1,116
Brenton Thwaites is listed (or ranked) 13 on the list Rank All of Taylor Swift's Exes
age 28

Allegedly, Brenton Thwaites and Taylor briefly dated in 2013.

14
259 1,096
Brandon Borello is listed (or ranked) 14 on the list Rank All of Taylor Swift's Exes
Brandon Borello

Brandon Borello was one of Taylor Swift's first exes. "Fifteen" and "Tim McGraw" were both inspired by the couple's 2005 relationship.

15
224 1,101
Jordan Alford is listed (or ranked) 15 on the list Rank All of Taylor Swift's Exes
Jordan Alford

Jordan Alford was Taylor's high school boyfriend. Apparently "Picture to Burn" is about him.

16
220 1,084
Evan Spiegel is listed (or ranked) 16 on the list Rank All of Taylor Swift's Exes

Taylor and Snapchat CEO Evan Spiegel dated briefly from December 2013 to 2014 after they met at a holiday party.

17
221 1,103
Toby Hemingway is listed (or ranked) 17 on the list Rank All of Taylor Swift's Exes
age 34

Apparently the two dated from July 2010 to October 2010.

18
185 1,150
Matt Healy is listed (or ranked) 18 on the list Rank All of Taylor Swift's Exes
age 28

Taylor was spotted hanging out with musician Matthew Healy in late 2014..