What You Don't Know About Taylor Swift's Past Relationships

What don't you know about Taylor Swift's past relationships? The singer-songwriter is often depicted as one of those stars who always has a new boyfriend. As she pointed out on Twitter, she sees this as a "deeply sexist" stereotype. While we don't want to fuel the flames, it can be pretty interesting to look back into the star's love life to see just how far she has come.

Swift has had a few serious relationships as well as several less serious boyfriends in her time. For the most part, she's tried to stay pretty private about her dating life. However, when a man makes an impact on her life, he often ends up featured in her music, so we do get a few clues about the nature of their relationship.

While most Swift fans probably already know the men she's been linked with in the past, some of these secrets about her dating history may come as a surprise.

Sam Amstrong might have been one of Taylor Swift's first (cheating) boyfriends

Before Taylor Swift was — well — Taylor Swift, she was just another high schooler looking for love. And by the sounds of things, it wasn't always easy. According to several reports, one of her first real high school boyfriends was a boy called Sam Armstrong. The internet learned about Armstrong's existence after he tweeted a picture of him and Swift alongside the captions, "What if I told I dated her??" and "True story" (via Babe.net).

Fans soon connected the dots and came to the conclusion that Armstrong was the inspiration for Swift's song "Should've Said No" (via Complex) — which is about a boy who cheated on her. As the lyrics go, "You should've said, 'No,' you should've gone home / You should've thought twice 'fore you let it all go." Sounds like Armstrong let it all go — and was still a little bitter about it on Twitter.

Rumor has it, Brandon Borello was Taylor Swift's first boyfriend — and her first muse

Another boy that Taylor Swift allegedly dated in high school was Brandon Borello. According to Complex, Borello was something of a muse for Swift — she actually wrote three separate songs about their relationship: "Tim McGraw," "Our Song," and "Fifteen." 

Apparently, she sang "Our Song" at a school talent show. The song has lyrics like, "Our song is the slamming screen door / Sneakin' out late, tapping on your window / When we're on the phone, and you talk real slow / 'Cause it's late, and your mama don't know." And as for "Tim McGraw," she wrote it about the fact that Borello, who was slightly older, was about to leave for college. With lyrics like, "When you think happiness / hope you think that little black dress / Think of my head on your chest / And my old faded blue jeans," it seems like Swift wanted Borello to remember her while he was away.  

Taylor Swift's high school boyfriend married her friend

Before Taylor Swift became a record-breaking artist, she was just another American high school student. In fact, in the early days, she kind of made a career out of her high school experiences! Back when she was still a teenager just starting out as a songwriter, Swift reportedly dated a high school classmate named Jordan Alford. As the Daily Mail reported, Alford was in the same year as Swift. The pair dated briefly in freshman year — until he transferred his affections to Chelsea, one of Swift's friends. Chelsea and Alford even ended up getting married.

As Chelsea explained, "We were kind of good friends at school, later not so much. She dated him, that's why." Additionally, according to Chelsea, Swift even wrote one of her earliest hits, "Picture to Burn," about the incident. "We just thought it was funny," Chelsea revealed. "[Jordan] was like, 'I'm not a redneck! She makes me look like some redneck!'" By the sound of things, this was one of Swift's first experiences with heartbreak — and maybe the first time she realized she could harness it for her music.

Joe Jonas broke up with Taylor Swift in a phone call

In 2008, Taylor Swift opened up about her relationship with Joe Jonas, another teen pop star. While fans may know that Swift and Jonas dated, they may not remember how it ended. As Swift said on The Ellen Show, her relationship with Jonas ended badly, or as she put it, "That's ouch." She went on to reveal that she wrote the song "Forever and Always" when the relationship turned sour.

Ellen DeGeneres then apologized for mentioning Jonas, to which Swift replied, "You know what, it's like 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 going to be able to remember the boy who broke up with me over the phone in 25 seconds when I was 18." She added, "I looked at the call log, it was like 27 seconds — that's got to be a record."

Years later in 2019, Swift confessed to DeGeneres that she regretted revealing that detail about their break up on TV. "That was too much," she admitted. But as things shook out, Jonas and Swift eventually made amends. "We laugh about it now," Swift explained (via Elle).

Taylor Swift fell for her You Belong With Me co-star Lucas Till

Most Taylor Swift fans probably remember romantic high school romance that played out in her music video for "You Belong with Me." In the video, Swift plays a dorky, unpopular girl with a crush on her neighbor, one of the popular jocks at her school played by Lucas Till. In the end of the video, the pair finally confess their feelings for each other at the prom. The pair certainly have a lot of chemistry — as it turns out, they actually got together in real life, too. At the time, Swift gushed about Till to MTV News. "[He] plays my love interest in the video, and he does such a great job," she said. "He's absolutely perfect for the part and really fun to be around, too." 

While sparks did fly between the co-stars, it didn't last long. Later that year, Till told MTV News, "We dated for a little bit. But, there was no friction because we were too nice." He added that there was no dramatic breakup, but instead, he liked her more as a friend. "That's the only reason that didn't work out," he said.

Taylor Swift fell in love on set again with Taylor Lautner

Shortly after dating Lucas Till, Taylor Swift met Taylor Lautner, star of the Twilight movies. According to InStyle, the pair probably met while filming the movie Valentine's Day. While the relationship didn't last long — they'd broken up by the time their movie was released — Lautner was around for one very famous moment. 

As it turns out, Lautner was actually on stage with Swift when she accepted the award for Best Video at the VMAs and was interrupted by Kanye West. As Lautner said in his opening monologue when he hosted Saturday Night Live in 2009, he wasn't exactly the best boyfriend in that moment. "I was actually at the VMAs the night she won the award for Best Video and Kanye West interrupted her speech," he revealed. "I was actually up on stage with her when that happened and as you can see, I really stood up for her." In a clip, Lautner can be seen awkwardly looking away. "I guess I could have done a little more," he added. He then proceeded to act out an alternate version showing off some pretty crazy martial arts skills.

Taylor Swift allegedly detailed her romance with John Mayer in Dear John

Taylor Swift didn't date fellow musician John Mayer for long. According to Billboard, the pair were only together for a few months at the beginning of 2010. However, we suspect that Swift's song "Dear John" was inspired by the relationship. The song features lyrics like "I lived in your chess game, but you changed the rules every day," and, "Don't you think I was too young to be messed with? The girl in the dress, cried the whole way home." This may have been a reference to the fact that she was only 18 years old at the time. Yikes, it doesn't sound like a particularly healthy relationship.

While Swift never confirmed if the song was about him, Mayer responded to the song in an interview with Rolling Stone. Apparently, he was "really humiliated" by the song. "It made me feel terrible," he confessed. "Because I didn't deserve it. I'm pretty good at taking accountability now, and I never did anything to deserve that."

Taylor Swift didn't date Cory Monteith for long, but she reportedly did write a song about him

Back in spring of 2010, rumors spread that Taylor Swift had started dating Cory Monteith, who portrayed Finn on Glee. According to Insider, the pair were together for less than a month. Rumor has it, the brief relationship inspired Swift's song "Mine." While Swift never revealed who the song was based on, many fans think it must be Monteith. As Swift told Yahoo! Music, the idea for the song came from one moment. "This is a situation where a guy that I just barely knew put his arm around me by the water, and I saw the entire relationship flash before my eyes, almost like some weird science-fiction movie."

As Swift went on to explain, the relationship "sort of fell apart, as things so often do," which would make sense considering how brief her relationship with Monteith was (via SongFacts). Sounds like this romance wasn't meant to be for Swift — but it definitely led to an iconic song.

Red might be Taylor Swift's only break-up album -- and fans think it's about Jake Gyllenhaal

Taylor Swift reportedly dated Jake Gyllenhaal from October 2010 to March 2011. Years later, in a 2020 interview with Rolling Stone, Swift spoke about her 2012 album Red. "I look back on this like this is my only true breakup album," she revealed. "Every other album has flickers of different things, but this was an album I wrote about a pure, absolute, to the core heartbreak."

As Rolling Stone noted in another article, there are some clues in the album that point to Gyllenhaal. For instance, in "State of Grace," Swift sings, "Just twin fire signs, four blue eyes" — Gyllenhaal and Swift have blue eyes and are Sagittarian. In another song, "All Too Well," Swift mentions a "scarf from that very first week," which many fans thought referenced photos of Gyllenhaal wearing Swift's old scarf (via The Verge).

The breakup may have been tough for Swift, but at least we got an amazing album out of it. As one fan wrote on Twitter, "I'd like to thank Jake Gyllenhaal for breaking Taylor Swift's heart because Red really is her best album."

Taylor Swift may have had one date with this Glee actor

In 2011, Taylor Swift was spotted with Glee's Chord Overstreet. As US Weekly reported at the time, the pair met up to watch an L.A. Kings hockey match before going out for a meal. One person at the game noted that "they looked pretty good together." As a source told the publication, "Chord is into her. He will definitely pursue this." Apparently, they were even thinking about writing a song together.

Later that year, however, Ryan Rollese, who worked with Overstreet's brother in the band Hot Chelle Rae, explained to US Weekly that the two never really got romantic. "They never actually dated!" Rollese said. "No, they were just hanging out... They got along very well because Chord's so outgoing and Taylor's very outgoing." Sounds like their first date (if it was a date) never blossomed into a romantic relationship and they decided to be friends instead.

Taylor Swift once dated the grandson of JFK

We bet you didn't realize that Taylor Swift briefly dated Conor Kennedy, the grandson of John F. Kennedy. In his book The Kennedy Heirs, J. Randy Taraborrelli dished about the pair's 2012 summer romance. Apparently, they bonded when Swift supported Kennedy after his mother's suicide. "Taylor was saddened when she heard the details of how Mary Kennedy had died," Taraborrelli wrote. "She was close to her own mother and couldn't imagine how Conor was able to go on after facing such tragedy."

Six weeks after their first date, Swift reportedly purchased a $5 million house in Massachusetts near the Kennedy home. A friend of Kennedy's told Taraborrelli, "Conor liked Taylor, don't get me wrong, but this business of her buying the house on the Cape made him nervous. It seemed as if she was getting a little too attached, spending five million bucks on a house just to be near the guy" (via US Weekly). The pair broke up after just two months and Swift sold the house a year later.

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Taylor Swift's relationship with Harry Styles is rumored to have inspired a lot of 1989

Harry Styles has gone down in history as one of Taylor Swift's most well-known exes. Even though the pair only dated for five months, they became pretty iconic in their time with many fans still obsessed with the pair. And for Swift, the relationship seems to have led to some serious creativity.

As Bustle noted at the time, "There are at least four songs on her brand new album 1989 that seem to be entirely about, or vaguely inspired by, Styles. In 'Out of the Woods,' Swift sings about an accident that involved 'twenty stitches in a hospital room.'" As Billboard pointed out, Styles had a snowmobiling accident with Styles on a trip to Utah. Additionally, in her aptly named song "Style," Swift gushes about a lover she compares to James Dean.

Even though Swift seems to have penned a few songs about Styles, the pair are clearly on good terms. As Styles shared on The Howard Stern Show, "It's flattering even if the song isn't that flattering." And, in 2021, the pair were seen chatting happily at the Grammy Awards (via Cosmopolitan).

Taylor Swift helped her boyfriend Calvin Harris write music

Taylor Swift reportedly dated Calvin Harris from early 2015 to June 2016, making this her first public relationship to last longer than a year. Shortly after the breakup, it was reported that the relationship fell apart because of a professional feud. Apparently, Swift had helped Harris write his song featuring Rihanna, "This Is What You Came For." As TMZ explained, "The problem in the relationship came the day the song was released." That day, Harris said that he didn't foresee working with Swift again.

Rolling Stone later confirmed that Swift had already collaborated with Harris under the pseudonym "Nils Sjoberg." That's when things got a little messy, with Harris going on a since-deleted Twitter rant about how Swift had revealed the news about the collaboration. "I know you're off [on] tour and you need someone new to try and bury like Katy ETC but I'm not that guy, sorry," he shared (via Vox). Yikes, it's clear this breakup was a pretty sour one.

Swift later referenced the drama with Harris in her music video for "Look What You Made Do" by including a gravestone in one shot that read "Nils Sjoberg."

Taylor Swift had a brief but intense relationship with Tom Hiddleston

After her long relationship with Calvin Harris, Taylor Swift got back into the dating scene pretty quickly. Days after her relationship with Harris was officially over in June 2016, she and British actor Tom Hiddleston were reportedly spotted kissing near her home in Rhode Island (via Cosmopolitan). Swift's relationship with Hiddleston ended two months later in September — but not before things got pretty intense between them.

Hiddleston met Swift's parents at their home in Nashville a few weeks after their relationship was made official, and Swift met his parents in England a week after that. Talk about things moving fast! A source even told E! News that Swift already thought Hiddleston was "the one." 

However, two months later, it was all over; US Weekly reported that the relationship was "too public" for Swift's liking. Sounds like this was a real whirlwind summer romance!

Taylor Swift has found a long-term partner and collaborator in Joe Alwyn

Finally, in 2016, Taylor Swift met a man who seems to be the real deal. Swift probably met Joe Alwyn in May 2016 at the Met Gala. As Elle noted, Swift's song "Dress" references a first meeting with a new crush that could easily be about Alwyn. After a super public relationship with Tom Hiddleston, Swift was careful to keep this burgeoning romance as private as possible. In fact, Alwyn didn't speak about Swift in public until 2018.

Swift and Alwyn lived together throughout the COVID-19 lockdown, and during that time, they learned that they actually made a pretty good professional partnership, too. In the film Folklore: The Long Pond Studio Sessions, Swift revealed that Alwyn had helped her write some songs on her Folklore album. "So, William Bowery is Joe... as we know," she explained. "Joe plays piano beautifully and he's always just playing and making things up and kind of creating things." She added that Alwyn had written the entire piano part of her duet "Exile." Though Swift eventually sang the song with Bon Iver, her original duet partner was Alwyn. So cute!