It is a staple of society to speculate about celeb lovelives, but in Taylor Swifts case this has been taken to the extreme. Known for her habitual dating and then tearing down of men Swift has quite the history of exs on her hands. We have decided to create some order in this messiness and rank T-Swifts top 20 boyfriends.
20. Drew Dunlap
Our Taylor’s first ever boyfriend, she and Drew Dunlap dated for a year, and while there is not much to say regarding this young love it is said that she had a necklace with his name on. Now that’s middle school commitment.
19. Jordan Alford
Pre-press, and pre-fame, Swift dated Jordan Alford in freshmen year of college, and while reports read that he left her for another woman, it is more so that things ended and then he ended up getting married and having children. Still high school heart break is high school heart break, and the childish affair resulted one of her most scathing songs ‘Picture To Burn’.
18. Martin Johnson
Swift and lead singer of Boys Like Girls, Martin Johnson met while writing a song together for the Hannah Montana soundtrack. While Swift fell head over heels for this punk rock leading man, the two were torn apart at the hands of her publicists. They did not think Johnson would be good for her image, breaking poor Swifts heart. The relationship is rumoured to have spawned ‘Love Story’.
17. Brandon Borello
Brandon Borello was such a staple in this singers heart that Swift reportedly wrote three songs about him! He was her high school boyfriend, who ending things mutually before moving to college. One such song was played at her school’s talent show titled, “Our Song.” Another was a parting gift called”Tim McGraw.” She wanted him to think of her whenever he heard a Tim McGraw song. How sweet.
16. Sam Armstrong
The first of her many relationships that ended post-success, and perhaps the inception of the broken-hearted girl trend, Armstrong was Swifts original high school sweetheart. While there is not much information on the pairs love life, he inspired the song ‘Should’ve Said No’ after cheating with another girl. Oh, young love!
15. Toby Hemingway
Taylor picks her men quite literally, as in she hand picked British actor Toby Hemingway to star as her love interest in the video for Mine. The pair apparently went on dinner dates in Maine and lunches in LA but nothing much seemed to come from this as 2010 was a busy dating year for the starlet.
14. Adam Young
In what was more of an online relationship, Taylor and Adam spent months exchanging email back and forth after a love at first sight meeting. For once Taylor didn’t come on too strong, in fact it was quite the opposite as Young gushed about his crush on the singer while she got busy with another guy. Sorry Adam, but a one-hit-wonder doesn’t quite cut it for Swift.
13. Chord Overstreet
After dating his Glee co-star previously, and after he also dated a fellow Glee co-star whose ex was also his Glee co-star, this Glee star dated T-Swift. Got it? Those Glee kids sure know how to get around. The pair had a short-lived fling as they were spotted getting cozy at a Hockey game before reportedly spending the night flirting at Harvey Weinstein’s pre-Oscar party, very upscale! Things soon fizzled out and by this point Glee was on the social decline and so Taylor never dated another one of them. Kevin McHale was most likely gutted.
12. Eddie Redmayne
Though Swift and Redmayne’s romance was nothing more than a mumbled rumour, having an oscar winner’s name in your little black book is a healthy notch to have. The pair met after she auditioned for Eponine in Les Mis – side note: could you imagine having to stare at Taylors annoying face in a super Tom Hooper close up, ugh – things didn’t work out as Taylor developed feelings too fast, and Redmayne wasn’t interested in a long-distance romance. For their first date T-Swizzle invited herself to his West End show, what a hun.
11. Zac Efron
Years ago Taylor was fairly vocal about her crush on Zac Efron, and apparently the feeling was mutual as rumours swirled of the pair dating in later 2010 fresh off both of their break ups. To deny the questions of a relationship the pair decided to write a duet and perform it on The Ellen Degeneres Show, because thats a normal way of deny romance of course. Anyway, we don’t know what came of this but the two looked super cute together regardless.
10. Lucas Till
Sometimes art imitates life, and especially so in this case as her on-screen lover became her real-life lover as Swift began dating We Belong Together leading man Lucas Till. While Taylor has never really revealed much about this relationship, Till was more than happy to sell her down the river after they broke up for fifteen more minutes of fame, well five. Apparently their relationship was just “nice”, no passion, no arguments, just nice. We get that feeling for Swifty, but on the plus side he called her a better kisser than his other alleged partner Miley Cyrus!
9. Cory Monteith
On reflection this relationship seems odder than most as we only imagine Monteith belonging with Lea Michele, but for a hot minute in 2010 he shared a sweet relationship with Taylor as the pair went on cute normal dates like bowling, or to the Grammys. Well normal for Taylor we guess. The pair met after her huge record Speak Now blew up and while Glee was still a thing. Apparently Cory was the inspiration behind Mine, a lucky escape for a Swift ex.
8. Connor Kennedy
Honestly, who better to have a summer fling with than a presidents nephew? The snaps of the pair frolicking on the beach and taking long walks on the beach made them look like a real life Hollister commercial. Stepping up the esteem value, Tay Tay showed that she was done dating Disney boys and was ready for something more, AKA a junior politician. Unfortunately for her she made a fatal error; she chose a Kennedy! Did Marilyn teach us nothing? After coming on too strong, too fast (and apparently holding an unhealthy obsession with his family), Connor did what any Kennedy would do – dumped the bitch.
7. Jake Gyllenhaal
Who would make a better coffee date than Jake Gyllenhaal? Is that even possible? We ask because that seems to be the only picture we could rustle up of the two, despite dating for months and even spending Thanksgiving together. After the private jets, weekend get aways, and … coffee dates, the pair eventually broke up when, you guessed it, she came on too strong and scared Jake off. Apparently Gyllenhaal was that big of a jerk she wrote the majority of Red about him, including the time he missed her birthday party. Truly horrific. The actor gets bonus points for allegedly being the one to take Taylors’ flower!
6. Tom Hiddleston
After less than two weeks following her high profile split from Calvin Harris, pictures emerged of Swift canoodling on a beach with British movie star Tom Hiddleston. The pair met prior to her split with Harris, leading to speculation of cheating. The following two months saw the pair arm in arm at every function, supporting one another’s careers with her showing up to film premiers and he attending her concerts in TS merchandise, and even meeting each others parents. Their respective careers is ultimately what tore the two apart, as the lovebirds began to row over their hectic schedules keeping them from seeing one another. Though the break up appeared amicable, Swift has yet to release an album so there may still be a track waiting with Hiddleston’s name on it.
5. Taylor Lautner
In quite possibly her sweetest relationship to date with little fall out during the split, T-Squared was a fan favourite pairing, right at the peak of Lautner’s popularity. Admittedly, the relationship was mostly loved due to the couple name but still, teeny boppers everywhere were losing their mind! Lautner was reportedly way more into Swift than she him which lead to the friend-zone jam Back To December, poor Lautner. The peak of their relationship? Him silently watching Kanye snatch the country singers VMA while standing 10ft away. Iconic.
4. John Mayer
Every good girl needs a bad boy, and in what was quite the surprising affair between 31-year-old lothario Mayer and ‘sweet’ 19-year-old Swift, she got just that. As if by clockwork a messy break-up was inevitable, spawning a war of songs between the two with taylor penning Dear John and Mayer retaliating with Paper Doll. Years later, things got even more interesting when Swift got into a highly publicised fued with Katy Perry, another of Mayer’s lovers. God bless that man.
3. Joe Jonas
Who could forget the 27-second phone call that ended it all? Jonas was the first high profile relationship T-Swizzle exploited for her own gain as she took to bashing him in almost every media outlet, and penned a supposed FOUR songs about the relationship. Swift even went so far as to tear down her ex’s new partner in Better Than Revenge; a stunning fued that still stands today according to Camilla Belle’s Instagram. She clearly got over thinks with Joe though, as the pair began double dating after he started seeing her BFF Gigi Hadid. Yeah, that’s kinda weird.
2. Harry Styles
Who can forget Taylor Swift and Harry Styles torrid love affair? For him she penned ‘Style’, and in return he wrote ‘Perfect’. Both the singers teeny bopper fandoms freaked out when photographs emerged of these two on a date. Several more images, and articles were printed in the months preceding but little news came directly from the two, until the break up bashing began. What is most notable from this A-list pairing was the bitter fued between the two fandoms following the pairs split.
1. Calvin Harris
By the point Swift and Harris dated they were both respectively at the top of their game. Each scoring number ones and winning awards they were a fully fledged power couple in the industry and their sickly sweet bae goals relationship was headline news the entire 15-months the two were together. Following the relationship the media focused on the two even more, as Harris dragged Swift on Twitter the same day Kim Kardashian, Kanye West, and Katy Perry each exposed the country bumpkin.