What Taylor Swift's Exes Have Said About Her Songs
Tom Hiddleston
After meeting on May 3, 2016, at the Met Gala, things between Taylor Swift and Tom Hiddleston escalated quickly. Some marveled over the "Hiddleswift" pairing, wondering if the affair was legit or simply a well-staged distraction from Swift's recent breakup with Calvin Harris and her issues with Kim Kardashian and Kanye West. Regardless of the reason, the pop star and the movie star were suddenly out everywhere, including Nashville, Tennessee, Swift's hometown, where Swift took Hiddleston to meet her parents.
However, things might have moved too swiftly because the pair called the jet-setting, PDA-filled romance off after only three months. Us Magazine quoted a source close to the couple who said Swift pulled the plug. "Tom wanted the relationship to be more public than she was comfortable with," they explained, adding that Hiddleston was "embarrassed that the relationship fizzled out."
He may have been embarrassed, but Hiddleston held his head high and proved that he is a perfect gentleman, although he plays Loki, a Marvel franchise villain. In a 2017 interview with GQ, he confirmed that the relationship was the real deal and sang the singer's praises, using words like "amazing" and "incredible." "She's generous and kind and lovely, and we had the best time." For her part, Swift did what she does best. She wrote a hit. Fans spotted Easter eggs hidden in the lyrics of "Getaway Car," which led to speculation that Swift penned the song about the affair.
Lucas Till
With their blonde-haired, blue-eyed, girl- and boy-next-door good looks, it's no wonder that sparks ignited between Lucas Till and Taylor Swift on the set of her 2009 video for "You Belong With Me." The song may not have been written about Till, but he was cast to star in the video as the object of Swift's affection. The singer told MTV that she and Till met nearly a year earlier, around the time he was filming "Hannah Montana: The Movie" with Miley Cyrus. He made quite the impression. "[He] plays my love interest in the video, and he does such a great job," Swift said about working with the up-and-coming actor. "He's absolutely perfect for the part and really fun to be around, too."
According to Till, the fun continued once the director yelled "Cut." In a case of life imitating art, he became Swift's off-camera love interest. In late 2009, Till admitted to MTV that he and the pop superstar briefly dated, but it never really went anywhere, saying that he thought of her more as a "friend." "That's the only reason that didn't work out," he said.
Ouch! Guess he didn't belong with her after all. But while that comment may have stung a little, Swift could lick her wounds knowing that her hunky co-star also told MTV that he preferred Swift's on-screen kisses to his co-star Cyrus. "I chose Taylor Swift and I'm gonna stick with that answer," he said. Nice save.
Jordan Alford
High-school heartaches are hard, and Taylor Swift had her fair share. Before she became Time's 2023 Person of the Year, Swift was just another student at Hendersonville High School in Tennessee, and, like most high schoolers, she had crushes and got her heart broken once or twice. But unlike most of her peers, Swift turned her disappointments into a staggering fortune by drawing on her experiences to write the songs that would turn her into the voice of a generation.
The track, "Picture To Burn," which appeared on Swift's first album in 2006 and was released as a single in 2008, is thought to be about a boy she dated during her freshman year at Henderson High, Jordan Alford. Alford dumped the future Grammy-award-winning artist for her friend Chelsea, the woman he would eventually marry. In an interview with Daily Mirror, Chelsea recalls how she and 14-year-old Swift got into a verbal altercation at their lockers over the situation. "We were 14, we were just being girly, snarky," she said.
Swift took the snark to new heights in the lyrics of "Picture to Burn," and although she doesn't call out Alford by name, her high-school honey and his wife got the message. "[Jordan] was like, 'I'm not a redneck! She makes me look like some redneck!' but other than that we just thought it was kind of funny," Chelsea said. It was Swift, however, who laughed all the way to the bank.
Stephen Barker Liles
When you're out on tour, all the traveling, long nights, and hotel stays can create an atmosphere that's ripe for romance. That may be why Taylor Swift crushed hard on vocalist Stephen Barker Liles of the country trio Love and Theft when the band opened for her on her 2008 "Fearless" tour. Supposedly, Liles was as enamored with Swift as she was with him, but the two deny ever mixing business with pleasure. Instead, they poured their hearts out in song.
Swift, who is notorious for keeping fans guessing when it comes to the men who inspire her hits, boldly titled her ode, "Hey Stephen." Liles admitted to being a little apprehensive when she told him because, let's face it, Swift's reputation preceded her. He needn't have worried, however, because Swift sang his praises. Liles told The Boot that he was "relieved" that she said good things about him in the song and called it "one of the nicest things anybody's ever done for me."
Around the same time that Swift was writing "Hey Stephen," Liles was writing a song inspired by the beautiful blonde called "Try to Make it Anyway." He told Taste of Country that it's "one of my favorite songs that I've ever written." Liles added, "I really dig Taylor," and said he hoped the megastar was "flattered" by his efforts. "As far as I know, none of the other dudes she's been hanging out with have written a song about her!"
Sam Armstrong
Most everyone has high-school tales of love and loss, but Taylor Swift can't seem to shake hers off. Instead, she mines them for hit songs, raking her exes over the coals for their bad behavior. In "Should've Said No," Swift blasts a boy who allegedly two-timed her. In an intro to the song at a concert shared on TikTok, Swift says, "This is a song I wrote about a guy who made the choice to cheat on me and probably shouldn't have because I write songs." Truer words were never spoken.
Where other men might hang their heads in shame over such a public revelation, Sam Armstrong took to his since-deleted Twitter — now known as X — account to proudly declare he dated Taylor Swift in high school and had photos to prove it. In doing so, he unwittingly started a firestorm of enraged Swifties who called him out as the cheater who took a beat-down in her song.
What's worse than being the target of a Swift song is being the target of a group of rabid Swifties who will support and defend the superstar at all costs? Armstrong learned that lesson the hard way when he got into a Twitter war with the Swift army. He defended himself against the cheating allegations in a now-deleted post saying, "The crazies are certainly out," and stating, "I get being a fan of someone ... but gat damn, you don't know her. Or me. Hush" (via Yahoo Entertainment). Should've kept quiet.