The one person whose dating history has been universally questioned, examined and scrutinized is Taylor Swift. Swift has been constantly at the center of rumors and discussions. ‘Does she date too much?’ ‘Is she crazy?’ Swift has even addressed these questions and the narrative of her as a crazy ex-girlfriend and serial dater in several songs, the two most notable being “Shake It Off” and “Blank Space.” “I go on too many dates, but I can’t make ’em stay. At least, that’s what people say,” she sings on the aforementioned “Shake It Off,” addressing the haters and the rumors. There is a lot of slut-shaming surrounding the relationships of Taylor Swift, but for true Swifties there is a different kind of fascination
How did Taylor Swift get here? Sure, there were plenty of men stealing her heart and plenty of relationships and dates. But, the truth seems to be more so that her songwriting and lyrics led us here more than any scandal or fairytale romance. Swift is known for her songwriting ability, her skill in being candid, addictive and relatable. It’s pretty hard to relate to an A-list celebrity about love and heartbreak but somehow Taylor Swift does it. Not only do fans relate, but they’re left wondering who exactly caused the heartbreak or the joy behind the music.
Who inspired the Taylor Swift songs that millions of people bought, sang along to, cried to and listened to on Apple Music (never Spotify)? Though it’s a daunting task to get them all in one place, someone has to do it. This is investigative journalism, after all. Here’s Taylor Swift’s dating history, including who Swift is dating now.
Joe Jonas 2008 – 2009
It all began in the summer of 2008. Swift and Joe Jonas were allegedly spotted hanging out, with the pair sparking a teen-dream romance, perfect for Swift fans and Jonas Brothers fans alike. Swift did not at first confirm she was dating Jonas, but eventually the truth came out… when things went awry.
Jonas broke up with Swift in what she said was a 27-second phone call, telling Ellen Degeneres that Joe Jonas’ action figure should include a phone which he could use to break up with the players.
Jonas went on to date Camilla Belle relatively quickly after his breakup with Swift. Swift allegedly wrote several songs about him, many of which are chronicled on her album Speak Now. The track “Forever & Always” from Fearless was also alleged to have been added to the album last minute as a kiss-off to the relationship.
Jonas seems to have a fairly amicable relationship with Swift now, despite the ugly breakup. Belle, on the other hand, is still not a fan of the singer after “Better Than Revenge,” supposedly alludes to “the things that she does on the mattress.” Belle is known to take to social media for subtle jabs at the singer.
Lucas Till 2009
Swift’s “You Belong With Me” music video costar admitted to a brief fling with the star. It doesn’t seem as though Till inspired any songs, so the relationship doesn’t sound like it was too serious. He did tell MTV that Swift was a better kisser than his fellow music video costar Miley Cyrus.
Taylor Lautner 2009 – 2010
Swift dated the actor Taylor Lautner after meeting on the set of Valentine’s Day, a movie in which they were both featured. Their relationship lasted only a few months, sparking debate on whether Swift and Lautner only dated for the sake of the movie’s publicity.
Swift seemed to strike back at these rumors with the eventual release of “Back To December,” a song which many believe is an apology to Lautner for taking his love for granted. Swift sings about missing her former boyfriend and says he was “so good to me, so right.” The song’s title references a possible December breakup, though it’s said they tried to make it work until the very beginning of 2010.
John Mayer 2010
The two celebrity spokespeople for high-profile dating originally teamed up to work on music together. Their similarities in terms of relationship-inspired lyrics might have made them a perfect match. John Mayer and Swift penned “Half Of My Heart” together, amongst others. It does not seem the relationship was long or stable, as Swift wrote the song searingly emotional “Dear John” for her album Speak Now, asking Mayer, “Didn’t you think I was too young to be played by your dark, twisted games when I loved you so?” Ouch.
Mayer eventually shot back, publicly expressing his disappointment in the song’s transparency to Rolling Stone. Mayer eventually wrote the song “Paper Doll,” which was alleged to have been about Swift and contains some obvious references to “Dear John.” One of these clues is his reply to Swift’s “Dear John” lyric, “You paint me a blue sky then go back and turn it to rain.” Mayer’s response? “If those angel wings don’t fly, someone’s gonna paint you another sky.” Also included are references to Swift’s “22” and “Red.”
Cory Monteith 2010
Swift and Glee actor Cory Monteith never confirmed their relationship, but they were seen together frequently. Swift, as usual, danced around the question, though Swift’s silence on The Ellen Show did seem to confirm a relationship when she was asked about a possible romance by Ellen Degeneres. Monteith was a bit more coy on the show with a giddy denial. The relationship ended for unknown reasons, but Taylor Swift did speak later on Twitter about Monteith’s tragic death in 2013, posting that she was “speechless.”
Toby Hemingway 2010
Toby Hemingway met Taylor Swift on the set of the music video for her song “Mine.” The two dated very briefly, if at all, and this pairing seems to be a hot debate among dedicated Swifties. They were seen out and about on a few occasions, but some say it was for the purpose of the aforementioned music video. The breakup, if there was one, was kept very quiet. It sounds unlikely, but controversial enough that it’s worth mentioning.
Jake Gyllenhaal 2010 – 2011
Jake Gyllenhaal was Swift’s next major romance, with the pair spotted out and about in New York holding hands. They dated for a few months from the end of 2010 to the very beginning of 2011, but rumors say the relationship was a little bit rocky, albeit serious enough that Swift met Gyllenhaal’s family. They may have broken up because Gyllenhaal supposedly did not attend Swift’s birthday party which led to unrest. He ended the relationship via text message.
The courtship and its end inspired several songs. Many tracks on Red are supposedly about Gyllenhaal, including “We Are Never Getting Back Together” and “All Too Well.” Hardcore fans will remember Gyllenhaal’s scarf as the pièce de résistance of Red. One of the (my) most beloved and emotional lyrics about the breakup? “You call me up again just to break me like a promise, so casually cruel in the name of being honest.”
Harry Styles 2011
There were several men speculated to be in Swift’s life between Gyllenhaal and the first coming of Harry Styles, but no photographic or even spoken proof of their relationships with which to substantiate. It seems that this period was mainly made up of casual dating for Swift. Though this alleged initial courtship between Swift and Styles was almost too brief to even include, there have been some telling statements and even a song about the singers’ first fling. Some say “I Knew You Were Trouble” is about Styles and their first meeting, and some Taylor Swift-sourced comments from a Vanity Fair article seem to almost confirm that point. The two may have flirted and casually dated, breaking it off after Styles didn’t consider the couple exclusive. Don’t worry, more of Styles to come.
Conor Kennedy 2012
Conor Kennedy and Taylor Swift’s relationship was a bit scandalous, providing tabloid fodder that led to some Swift backlash. The more hopeful and romantic songs on Red are said to be about Kennedy, including “Begin Again.” Kennedy and Swift, by all accounts, were a very harmonious couple, to the point that Swift majorly bonded with the Kennedy family and they even inspired their own song “Starlight” on Red. Conor Kennedy was a bit younger than Swift, and still a student, and gossip reported that she even was considering buying a house near his. Swift replied that the Massachusetts property was for investment purposes, having nothing to do with her personal life. The two broke up after several months of dating, reportedly due to distance.
Harry Styles 2012 – 2013
He’s back. The One Direction singer and Swift rekindled their brief fling, with confirmation in the form of photos of them holding hands in Central Park. Swift and Styles only publicly dated for a month, but the couple traveled together often and seemed perfect together. They may have broken up on vacation together, which sounds like a really great trip.
Styles inspired several songs on 1989 including “Out Of The Woods.” One telltale sign of the song’s inspiration? The mention of their shared paper airplane necklaces. Styles eventually fired back at Swift’s lyrics on the One Direction song “Perfect.” Styles sang, “If you’re looking for someone to write your breakup songs about, baby, I’m perfect.”
Calvin Harris 2015 – 2016
For a bit, Taylor Swift took a conscious step away from public dating. Eventually, hugely successful DJ Calvin Harris and Taylor Swift began dating in March 2015. Their relationship would be Swift’s longest to-date, with the pair being together for a bit over a year, from March of 2015 to June of 2016. They shared adorable photos on Instagram, bought each other gifts and even wrote songs together. Unfortunately, the songwriting may have been what caused the end of the relationship, with the ghostwriting drama around “This Is What You Came For” sparking a now-deleted Calvin Harris Twitter rant… approved by alleged Swift enemies Katy Perry and Camilla Belle.
It’s not yet known which songs Harris will inspire, but if Swift is consistent, there will be an album in the fall of 2016. Hopefully, her newest work will include some candid songs about their breakup.
Tom Hiddleston 2016
Swift’s most recent relationship was with British actor Tom Hiddleston. They met at the Met Ball and video evidence shows that they even shared a dance. Their romance was confirmed by photos of them kissing on beachside rocks in June and they haven’t been out of the paparazzi’s lens since. They’ve been seen traveling, meeting each other’s families and even with Hiddleston wearing an “I [heart] T.S.” tank top. Subtle.
If you ask me, something about this latest love seems fishy and there are several conspiracy theories about the actual status of their relationship. My favorite? Hiddleston and Swift are just working together for the release of her latest single and music video, which might chronicle dating while in the limelight. If there’s anyone who knows a lot about that subject, it’s Taylor Swift.
After only three months of dating, Hiddleston and Swift called it quits. So far, no music video has premiered and there has been no proof to the conspiracy theories, so if anything it seems that this relationship was genuine… and will provide some fuel to Swift’s songwriting.