Culture Rank All of Taylor Swift's Exes  

Jessica Lawshe
34.4k votes 4.3k voters 84.9k 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
1,522 1,347
Harry Styles is listed (or ranked) 1 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.

2
1,591 1,425
Taylor Lautner is listed (or ranked) 2 on the list Rank All of Taylor Swift's Exes
age 26

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

3
1,450 1,297
Jake Gyllenhaal is listed (or ranked) 3 on the list Rank All of Taylor Swift's Exes
age 35

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.

4
1,095 947
Tom Hiddleston is listed (or ranked) 4 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."

5
1,022 909
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
954 1,434
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
646 1,257
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
671 1,317
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
554 1,203
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
635 1,443
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
577 1,328
Cory Monteith is listed (or ranked) 11 on the list Rank All of Taylor Swift's Exes
Dec. at 31 (1982-2013)

Taylor and the late Glee star allegedly dated in 2010.

12
375 1,181
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
336 1,138
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
262 1,118
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
227 1,127
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
222 1,109
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
222 1,127
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
188 1,178
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..