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Maneater: A Closer Look At Taylor Swift’s Many Past Boyfriends

Darren July 5, 2023

It’s no secret that Taylor Swift is one of the most popular pop stars on the planet today. She’s won many Grammy and Emmy Awards as one of the world’s most successful artists. However, music isn’t the only thing that Swift is famous for. She’s also – perhaps infamously – had many boyfriends and writes about her experiences with them in her songs and albums.

It’s one of Swift’s trademarks and also one of the hazards of dating her. Legions of fans, called ‘Swifties,’ have come to expect to learn about her doomed relationships when they listen to her songs. So today we’ll look back at her many boyfriends and see who had the most notable impact on her life. If you’re a Taylor fan, it will be fascinating to see because it’s a very long list. Let’s get started here.

Brandon Borello

Borello has the dubious honor of being the first of Swift’s many boyfriends. The pair dated in high school when Swift’s family lived in Tennessee. But it came to an end after he moved to college and their relationship became unsustainable. Borello probably had no idea that his childhood sweetheart was going to become a superstar (via CBS News).

It isn’t easy to find information about him (or photos of him) because he’s a normal man living a regular life. He inspired the song Tim McGraw but that’s his main claim to fame. According to Swift, Borello bought the album and told her that he loved it but it still didn’t impress his new girlfriend. At least the song didn’t scorch him like the fashion that some of her later boyfriends experienced.

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Jordan Alford

Alford was another of Swift’s childhood conquests where her fans don’t know much about their relationship. He inspired her enough to feature in one of her songs but he doesn’t emerge with much credit. She called him a redneck who didn’t allow her to drive his truck. That’s one of the most Tennessee things we’ve ever read.

These sentiments feature in the track Picture to Burn. This shows that all of Swift’s many boyfriends leave enough of an impression to stimulate her creativity. Maybe that’s not what most men want but it’s a risk they take when they date the Grammy winner. Everybody knows what’s going to happen (via Just Jared).

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Drew Hardwick

Technically, we’re cheating by including Hardwick on this list because Swift didn’t date him. However, she obsessed over her high school classmate enough to write one of her most famous early hits. Teardrops On My Guitar was very popular and has hundreds of millions of views on YouTube.

Hardwick admitted that he never realized that Swift had feelings for him. Later, he served in the military but his story takes a dark turn. Police arrested him for child abuse after he hit a three-year-old girl in 2015. It’s safe to say that Swift won’t be writing any more songs about the convicted felon (via Taste of Country).

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Sam Armstrong

These days, it’s ridiculous to think that anybody would cheat on Swift because she’s one of the most eligible women on the planet. Meanwhile, there’s a massive risk that she would destroy them in her next album. Unfortunately, Armstrong learned this the hard way because he didn’t expect his prom date to become a superstar.

He cheated on her and broke her heart so she tore him apart in Should’ve Said No. These days, Armstrong spends time writing horrible things about his ex on Twitter. He’s a bit of a loser because it’s sad not to move on. In the end, he was an idiot and he paid a massive price for this. Armstrong is one of the most bitter of her many boyfriends (via The Best Social Media).

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Joe Jonas

Jonas was Swift’s first celebrity boyfriend. They had a short relationship but it had an explosive ending. He infamously ended things over the phone in an abrupt call. The ‘Swifties’ turned against him instantly because he treated their adored Taylor like dirt. Meanwhile, she wrote a song about the experience called Forever and Always that sliced him apart.

Swift told Ellen: “When I find that person who 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.” This wasn’t the proudest moment of Jonas’s life but they reconciled when they grew up (via Cosmopolitan).

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Lucas Till

Till and Swift dated for a short while after he appeared in her You Belong With Me music video. They were young and instantly had a connection but they agreed that they didn’t have a meaningful romantic connection. That doesn’t mean that they don’t get along because they still like each other today.

He told MTV: “There was no friction because we were too nice. We just really both liked each other. 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 (via Today)”.

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Taylor Lautner

The Twilight franchise turned Lautner into one of the hottest breakout stars of the late 2000s. He met Swift when they both featured in the movie Valentine’s Day and hormones raged. They dated for almost a year before they called it quits. This was long enough for him to inspire a song; Back to December.

Allegedly, he had stronger feelings for her than she did for him and it didn’t work out. She wrote the track as an apology to her ex-boyfriend because she knew that she hurt him with her coldness. However, the relationship wasn’t going anywhere and she didn’t want to drag out the inevitable (via Us Magazine).

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John Mayer

Mayer was 32 when he began dating the 19-year-old Swift in 2009. This was the biggest age difference that she had experienced as she tested the waters with a mature man. However, it didn’t work out well because they split after a few months. Meanwhile, Swift had to tell her fans to stop cyberbullying her fellow artist (via SheKnows).

This didn’t stop her from writing a batch of songs about Mayer, including I Knew You Were Trouble. This didn’t impress him and he referred to her practice as ‘cheap songwriting.’ But it sent her fans into a frenzy because they lap up the scandal and gossip. Unfortunately, Swift’s reputation precedes her and doesn’t help her relationships with her many boyfriends.

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Cory Monteith

It’s too strong to call Monteith one of Swift’s many official boyfriends. But they did go on a few dates across a month and she always maintained an affection for the Canadian actor. The Glee star’s tragic death rocked her when she heard the news and she has nothing but good things to say about him.

Swift also wrote the song Mine about him and suggested that she wished they had more time together. Tragically, Monteith struggled with drug abuse and died of a heroin overdose in his hotel room in 2013. It was a massive loss because he was a decent human with more to give the world (via Page Six).

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Jake Gyllenhaal

This was one of Swift’s most high-profile relationships because Gyllenhaal is also a superstar. The pair dated briefly but it was long enough to leave an impression on the singer. Their connection and break-up inspired the album Red as she immortalized their time together. He allegedly failed to appear for her 21st birthday and she wrote about this in the song All Too Well.

In the end, they went in different directions but Swift learned a lot. It’s safe to say that her fanbase doesn’t love Gyllenhaal because of the way he allegedly treated her. In 2011, there were rumors that they rekindled their romance but that wasn’t true. Swift has had many boyfriends but this was one of the few times she dated someone more famous than her (via People).

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Zac Efron

Rumors swirled that Swift and Efron were dating in 2011 but both parties furiously denied it. However, Ellen DeGeneres threw gasoline on the flames when she invited them on her show. She insisted that they had a history and even gave them t-shirts alluding to their alleged romance (via Hollywood Life).

Then, when Swift returned in another appearance, Ellen referred to it again. However, Swift shut her down emphatically as she showed that she didn’t have time for this. She also asked Ellen to stop asking her about her many boyfriends because it was ‘depressing.’ Even if she didn’t date Efron, it provided a lot of media fodder for Ellen.

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Patrick Schwarzenegger

There were rumors that Swift was dating Arnold Schwarzenegger’s son Patrick in 2012. The latter was studying at USC and spent time with the pop sensation on Independence Day. It’s unusual for Swift to appear publicly with any of her many boyfriends unless they’re in a serious relationship.

However, it’s possible that they were only friends because he helped introduce her to the Kennedy clan. Very soon after, Swift began dating Conor Kennedy so maybe Patrick found himself in the friend zone. Many people thought that the hunky young man was a better catch than Conor but that’s debatable (via E! News).

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Conor Kennedy

Swift attracted criticism when she dated Robert F. Kennedy’s grandson, Conor. That’s because she was 22 while he was just 18 but their relationship didn’t last for long. They had another whirlwind romance as she added him to her list of many boyfriends. She met the family after she wrote the song Ethel in celebration of Bobby and Ethel Kennedy’s love story.

This connected her to Conor and the young couple had a short tryst. They even gatecrashed a family wedding despite Conor’s aunt forbidding Swift’s attendance. She didn’t want the singer to take attention away from the bride but they went anyway. In the end, their bond dissolved after a few months (via InStyle).

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Harry Styles

True, Swift has had many boyfriends as you can see by now, but Styles was one of the most popular. The former One Direction singer and Swift appeared to be a match made in heaven. But they only dated for four months even if felt like it was forever. Allegedly, they met for the first time backstage at the 2012 Kids Choice Awards and instantly vibed.

The paparazzi snapped them walking together in Central Park amid rumors of a real-life love story. However, friction arose when they went on vacation to the British Virgin Islands. They had differences of opinions about the future of their relationship and they broke up. Swift wrote about Styles in the album 1989 but they remain on good terms (via Hello!).

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Karlie Kloss

Yes, we know we’re cheating by including a woman but this is too juicy to leave off this list. Swift and Kloss were devoted friends but Internet users theorized that their relationship went beyond this. #Kaylor became a popular trend on Reddit as well as other forums where speculation about Swift’s sexuality was rife (via Distractify).

The peak of their connection was in 2014 when they appeared to be inseparable. Meanwhile, they appeared on Victoria’s Secret runways together several times and drove fans into a frenzy. Some Swifties think that several songs from Folklore allude to her alleged romance with Kloss, including Betty. But nobody knows for sure except both of them.

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Calvin Harris

Harris raised eyebrows when it emerged that he became the latest of Swift’s many boyfriends in 2015. The English DJ had a one-year romance with the pop sensation and this inspired a lot of musical material. She wrote at least four songs about their doomed relationship but he didn’t emerge with much credit.

The timing was surprising because they recently posted steamy beach pictures together. But allegedly, Harris instigated the break-up because he had enough of the stresses of dating Swift. Many men can’t handle the demands that come with being with a true superstar. Unfortunately, Harris was one of these despite his high profile (via Elle).

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Tom Hiddleston

Hiddleston is up there with the most famous of Swift’s many boyfriends. The pair had a short-lived romance that involved a lot of PDA. In the picture below, we can see them kissing on a beach in Rhode Island. Meanwhile, Hiddleston also infamously wore an “I Love TS” t-shirt in a cringe-worthy move. Some people thought that their relationship was fake and they wanted to use it to enhance their brands.

Unfortunately, ‘HiddleSwift’ crashed apart after three months of torment. Allegedly, Swift wasn’t happy because Hiddleston wanted to be more public. She refused to attend the Emmys with him too because it made her uncomfortable. Furthermore, their relationship may have damaged his hopes of landing the coveted James Bond role (via The Mirror).

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Joe Alwyn

Everybody thought that Swift had finally found the one whom she was going to settle down with. After trawling through many boyfriends she had her longest relationship with Alwyn. She dated the Normal People star for six years before they finally called it quits in 2023. This rocked Swift’s fanbase because they didn’t see it coming.

Swift and Alwyn kept a relatively low profile unlike many of her previous romantic relationships. However, it drained Alwyn because Swift receives so much attention. It’s difficult for them to do anything normal like go for a hike or pop to the grocery store without paparazzi or fans annoying them (via Teen Vogue).

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Matt Healy

Everybody needs a rebound after they come out of a long-term relationship. It doesn’t matter if it doesn’t make sense because we know it won’t last. Swift fell into the sleazy arms of the 1975’s polarizing singer Matt Healy in 2023. They had a whirlwind romance that even saw Healy fly from the Philippines to see Swift perform in her beloved Nashville.

Witnesses saw them cuddling and kissing at various events before it came to an end. They realized that their schedules weren’t compatible and decided it was best to finish on good terms. It’s also worth noting that in 2016 Healy said that dating Swift would emasculating. But he changed his tune pretty quickly when the opportunity arose (via Glamour)!

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Austin Reaves

Reaves became one of the latest rumored figures on Swift’s hitlist in 2023. After she split from the aforementioned Healy, she went in a different direction by dating the Lakers star. This was the first time that she dated an elite athlete as she broke from her regular type. Fans spotted Swift with the NBA player in an Arkansas bar and rumors instantly began.

Later, Reaves’ brother cleared the air and denied that anything happened. But where there’s smoke, there’s usually fire and fans continued to spread the story. Nobody can blame Reaves for wanting to date one of the most beautiful and talented women on the planet. Meanwhile, he’s no gold digger because the Lakers just signed him to a $58 million contract (via Seventeen). We’ll see if Reaves gets added to the already lengthy list of Swift’s former boy toys.

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