Taylor Swift has had her fair share of romances.

While critics like to point out the number of people Swift has dated

it really is no different from most other people if their dating timeline was revisited from high school age through their thirties.

The only difference is that Swift’s relationships play out publicly rather than privately.

While Swift does not speak about her romances with any frequency, she does put them in her songs.

Be it for being in love, heartbreak, and everything in between, Swift’s music is how she processes the emotions she has for the men she loves or loved, as seen by the songs Swift sings that leave her in tears on stage.

Swift puts her all into her relationships and allows herself to fall in love unapologetically. This is something that has led to great love and great heartbreak, as well as some unforgettable songs along the way.

While Swifties know how many boyfriends Taylor Swift has really had, the media has linked Swift to men she was never involved with. This is clear by the fact that they are not referenced in any songs, as those who have been linked to Swift know all too well that they likely will be on an album down the road, which is not only cathartic for Swift but allows fans a glimpse into what made some relationships work and what caused them to end.

From her teenage years through her thirties, Taylor Swift has had 12 high-profile boyfriends

The world started paying attention to who Swift was dating when she was 18 years old. While the media likes to make a big deal out of how many people Swift has been in a relationship with, when broken down between her teens and thirties, the number is not large at all.

It is the fact that the people whom Swift has dated are public figures themselves; the interest in the relationship is multiplied several times or more, depending on the level of fame Swift’s boyfriend has achieved.

Despite the fact that dating high-profile people means more media attention, this has never deterred Swift from following her heart. Instead, she prefers to “fall hard” and make her relationships a priority.

“The way I look at love is you have to follow it, and fall hard, if you fall hard. You have to forget about what everyone else thinks. It has to be an us-against-the-world mentality. You have to make it work by prioritizing it, and by falling in love really fast, without thinking too hard. If I think too hard about a relationship I’ll talk myself out of it,” Swift explained.

“I have rules for a lot of areas of my life. Love is not going to be one of them.”

Because of this mentality, Swift has dated some of entertainment’s who’s who. While the romances may not have all ended well, they have helped Swift learn about herself and what she wants from a partner along the way.

While there were a few relationships that lasted and looked promising for Swift, the majority can be chalked up to young love. But except for one ex, all have been forever memorialized in Swift’s music — some for the better, but most for the worse.

Taylor Swift’s Very First Publicly Known Boyfriend Made Headlines

Taylor Swift and Joe Jonas dated from July 2008 to October 2008

The first relationship to make headlines for Swift was when she was 18 years old. At that time, she was dating Joe Jonas, who she met while she performed with The Jonas Brothers on their Burnin’s Up Tour.

Swift was quickly rising up the charts as a pop country star and The Jonas Brothers, one of the most popular bands of the year. The media attention on the two was constant.

The relationship with Jonas lasted from July 2008 to October 2008.

According to Swift, the relationship ended because Jonas became interested in someone else. That someone else was Camilla Belle, who would ultimately not be in a relationship with Jonas longer than Swift was.

In a rare moment, Swift spoke publicly about how the breakup occurred when she was on The Ellen DeGeneres Show. It was not done face to face or even by having a conversation over the phone. Instead, it was done via a voicemail that Jonas left for Swift, which is how Jonas became fodder for some of Swift’s songs.

“Someday, I’m gonna find somebody really, really, really great, who’s right for me,” Swift explained.”When I find that person that is right for me, he’ll be wonderful and when I look at that person, I’m not even gonna be able to remember the boy who broke up with me over the phone in 25 seconds when I was 18.”

The two were eventually able to have a friendship in the years after their breakup thanks to Swift being friends with Sophie Turner first. Swift even admitted in 2019 that calling out Jonas on The Ellen DeGeneres Show was “too much.”

But when Jonas and Turner announced they were divorcing in 2023, Swift loaned Turner an apartment she owned in New York City. Whether this was taking sides or just helping out a friend was not clear. However, Swift has been seen hanging out with Turner rather than Jonas, which says a lot about where things stand.

Last Kiss; Forever & Always; Mr. Perfectly Fine; You All Over Me; Holy Ground

Taylor Swift Dated Three People Besides Joe Jonas In Her Teens

Taylor Swift dated Lucas Till, Taylor Lautner, and John Mayer in her teens

Swift took some time after her breakup from Jonas to get back on the dating scene. When she did, there were three men that Swift dated while still in her teens. Two inspired songs. One did not.

Lucas Till: March 2009 to April 2009

Lucas Till and Swift met while filming the music video for Swift’s song “You Belong With Me.” While the two thought that there might be something there, as it turns out, the relationship fizzled quickly. But the two were able to remain friendly after things ended.

“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,” Till explained. “That’s the only reason that didn’t work out.”

Taylor Lautner: October 2009 to December 2009

Taylor Lautner and Swift met while they were filming Valentine’s Day. The on-screen romance quickly turned to an off-screen one. However, Lautner and Swift did not ultimately work out. A lot of this had to do with “the relationship as not developing into anything.”

“He liked her more than she liked him,” a source revealed. “He went everywhere he could to see her, but she didn’t travel much to see him.”

This was one relationship that Swift looked back on and wished that she had done things differently. Lautner is one of the few exes that have had a song written about them that is kind to the ex and, more or less, points out what Swift did wrong.

John Mayer: December 2009 to February 2010

Swift and John Mayer met in 2009 after Mayer tweeted that he wanted to collaborate with Swift on a song. Swift later agreed, and the two eventually wrote, “Half of My Heart.”

“There’s no better way to put it out into the universe than to tweet it,” Mayer explained, “but then it’s not like she reads the tweet and goes, ‘I’m in,’ although she may have. I don’t remember.”

The collaboration and time spent together led the two to begin a whirlwind romance that began shortly after Swift and Lautner were no longer together. The two were spotted several times together. However, after just a few months, the two split up.

There were some bad feelings from the split and the relationship in general on Swift’s end, which is what led her to write about Mayer in a few songs — one of which was “Dear John.”

“A lot of times when people’s relationships end, they write an email to that person and say everything that they wish they would have said,” Swift explained. “A lot of times they don’t push send.”

While it was hard to do, Swift not only wrote about her relationship with Mayer but said that “putting it on the album was pushing send.”

In response, Mayer has said that the song made him “feel bad.”

“Because I didn’t deserve it. I’m pretty good at taking accountability now, and I never did anything to deserve that,” Mayer said. “It was a really lousy thing for her to do.”

Mayer went on to say, “I never got an email. I never got a phone call. I was really caught off-guard, and it really humiliated me at a time when I’d already been dressed down. I mean, how would you feel if, at the lowest you’ve ever been, someone kicked you even lower?”

Mayer later released “Paper Doll,” which fans speculated was about Swift, given all the references to her songs and lyrics in the lyrics Mayer wrote.

Swift and Mayer have since “called for peace” among fans. However, this does not mean they are friendly with one another, suggesting John has never truly been able to move on.

Taylor Swift Dated Five People Before Joe Alwyn In Her Twenties

Taylor Swift dated Jake Gyllenhall, Conor Kennedy, Harry Styles, Calvin Harris, and Tom Hiddleston in her twenties

Joe Alwyn was the one that Swifites thought that Swift was going to end up with. But before she dated him, there were a few other people Swift got into a relationship with. Most of which did not last long at all.

Jake Gyllenhaal: October 2010 to December 2010

Jake Gyllenhaal and Swift were set up by Gwyneth Paltrow and Chris Martin when the couple was still married. Swift and Gyllenhaal apparently hit it off, as they started dating and had a relationship that lasted for three months.

While Swift and Gyllenhaal were spotted together several times and Gyllenhaal took Swift to his sister, Maggie Gyllenhaal’s house for Thanksgiving, the amount of attention that the couple had made Gyllenhaal uncomfortable. It was also divulged that Gyllenhall said the age difference played a part in the breakup as well.

Conor Kennedy: July 2012 to October 2012

Conor Kennedy and Swift dated for a short time in 2012. However, things began to fizzle when Swift’s career became too demanding, and she was unable to make the relationship a priority. There were no hard feelings. It was simply a matter of the wrong time for the relationship.

Harry Styles: November 2012 to January 2013

When Harry Styles started dating Swift, he was in One Direction and Swift had solidified herself as a bonafide pop star. They appeared to be a pop royalty match made in heaven.

The two met at the 2012 Kid’s Choice Awards. They spent both Swift’s birthday and the holidays together. After New Year’s, Styles and Swift went to the Caribbean together. It was there that an argument of some sort was had and Swift left the island alone.

In the years since, Swift and Styles are in a great place with one another. There is apparently no bad blood between the two.

Calvin Harris: March 2015 to May 2016

In another friend set up, Calvin Harris and Swift met backstage at the Elle Style Awards in 2015 when their mutual friend, Ellie Goulding, introduced them. The two hit it off immediately. Harris and Swift both attended the Brit Awards the following night and went to the after party together.

It was just a few months later that the two were spotted attending the Billboard Music Awards together, officially as a couple.

Swift and Harris were ultimately together for 15 months before breaking up. Harris took the break-up hard and lashed out at Swift on Twitter (now X), a move years later he said that he regretted.

“For both of us, it was the wrong situation,” Harris said. “It clearly wasn’t right, so it ended.”

Tom Hiddleston: May 2016 to September 2016

Tom Hiddleton and Swift surprised fans when they started dating in May 2016. The two met at the 2016 Met Gala and had a great time during the summer. Hiddleston was seen wearing a shirt that read, “I Heart T.S.” at a Fourth of July party and the two were photographed with Hiddleston’s mom.

Given how short the relationship was, some thought the relationship was a PR stunt, but Hiddleston himself confirmed that his relationship with Swift was very real.

“Taylor is an amazing woman,” Hiddleston said. “She’s generous and kind and lovely, and we had the best time. Of course it was real.”

Joe Alwyn Looked To Be Taylor Swift’s Forever Love
Taylor Swift and Joe Alwyn were together from January 2017 to February 2023

Joe Alwyn and Swift met at the same time that Swift met Hiddleston at the 2016 Met Gala. The difference is, Hiddleston and Swift started a romance, while it took Alwyn and Swift a bit longer before they got together.

It was first reported that Alwyn and Swift were a couple in May 2017. However, a diary entry from Swift’s deluxe edition which was dated January 2017, stated that they had “been together for three months.” The two were together for quite a bit longer than originally reported.

 

Taylor Swift And Matt Healy Rekindled A Romance That Burned Out Quickly

Taylor Swift dated Matt Healy from May 2023 to June 2023

Fans were very surprised to see Swift and Matt Healy together as their romance made headlines in May 2023. However, the two had known one another for years and even sparked romance rumors in 2014, rumors that Healy shut down for years.

“I didn’t even date Taylor, but the media’s incessant and brutal obsession with her has meant that even a guy who DIDN’T DATE HER has been so battered by their never-ending questions that he’s inevitably said something that can be lifted and molded into something that resembles ‘shade’,” Healy said. “It’s really sad.”

That appeared to change in May 2023 when Healy and Swift were spotted out together in New York.

Healy went on tour in the Philippines shortly after that and was caught mouthing to the camera on stage, “This is about you. You know who you are. I love you.”

Healy appeared at the Eras Tour a few days later. During that concert date, Swift turned to the camera on stage and said, “This is about you. You know who you are. I love you.” The two appeared to be mouthing secret messages to one another.

Fans did not like the match because of the racist comments Healy had made about Ice Spice, a contributor on Swift’s remix of “Karma.”

But Swifties did not have to worry about the relationship for long, as Swift and Healy had broken up by June 2023.

Travis Kelce Publicly Let The World Know He Was Interested In Taylor Swift

Taylor Swift and Travis Kelce have been together since September 2023

Just when it looked like Swift might be taking a break from the dating scene, an unexpected love interest popped onto the scene.

Travis Kelce attended the Eras Tour in July 2023 in Kansas City. At that time, it was his intention to give Swift a friendship bracelet with his phone number on it. However, Swift did not allow him backstage so that she could save her voice and get some rest before her next performance.

“I was disappointed that she doesn’t talk before or after her shows because she has to save her voice for the 44 songs that she sings,” Kelce explained, “so I was a little butt-hurt I didn’t get to hand her one of the bracelets I made for her. She doesn’t meet anybody, or at least she didn’t want to meet me, so I took it personal.”

After Kelce had made the comment on his New Heights podcast, he started getting questions about whether Swift had responded to him. All of which he refused to comment on.

However, Kelce’s shot worked as fans were ecstatic to see Swift in attendance at the September 2023 game versus the Bears.

While many thought this was the couple’s first date, it was actually the hard launch of their relationship. The two had been together for weeks before Swift attended the Chiefs’ football game.

Since that time, Kelce and Swift have been going strong. “I love you’s” have been exchanged, Kelce has attended multiple Eras Tour dates, and a few songs were written about Kelce on The Tortured Poets Department. ​​​​​​​