Taylor Swift has been in the spotlight since she was 16, and, as she grew up in the spotlight, she has also experienced dating in the public eye. And over the years, Taylor Swift has experienced countless misogynistic remarks from strangers over her dating history. From people complaining about how many people she dated (which weren’t that many), to jokes about using her personal life to write her songs, people are still stuck with the 2013 mentality when it comes to Swift’s boyfriends. So let’s take a look at all her boyfriends, ranked from our least, to our most favorite!
11. Matty Healy
Cue to “The Smallest Man Who Ever Lived.”
Matty Healy and Taylor Swift’s relationship might’ve been short, as it lasted just a bit over a fortnight, but their romance had been a long time coming. There were rumors about the two of them going on for almost a decade, and they got together in the Spring of 2023. Due to the public pressure and other details we might never know, Healy allegedly ghosted Swift after promises of forever. Healy is believed to be the target of her vitriol on her latest album, The Tortured Poets Department.
10. John Mayer
Taylor Swift and John Mayer were briefly linked in 2009 as they collaborated on the song “Half of My Heart.” Although Mayer initially praised Swift’s writing skills, he belittled her after their breakup, which resulted in the famous breakup song “Dear John” from 2010’s Speak Now. He responded with “Paper Doll.” The worst detail about their short-lived romance is that Taylor was barely 19, and Mayer was 32.
9. Jake Gyllenhaal
Since Jake Gyllenhall never gave back Taylor’s scarf, he is pretty high on the “worst boyfriend” list. The actor and Swift dated briefly in 2012, and he’s believed to be the inspiration behind Swift’s masterpiece “All Too Well,” and its longer version, “All Too Well (10 Minute Version).” The brief affair had a huge emotional impact on Swift, who was 20 at the time, meanwhile, Gyllenhaal was almost 30.
8. Calvin Harris
Taylor Swift’s romance with DJ Calvin Harris was the most public she’s ever had. The singer posted many pictures of the two of them during their relationship between 2015 and 2016, which at the time was her longest relationship to date. As it turns out, they co-wrote Harris’ hit single with Rihanna, “This Is What You Came For,” though he had tried to discredit her skills beforehand by claiming he wouldn’t collaborate with her, and jumped on the hate train as soon as her reputation took a hit. They’re no longer on speaking terms, but Calvin’s wife admitted to listening to Taylor when he’s not around.
7. Joe Alwyn
Joe Alwyn was Taylor Swift’s longest relationship, and things between them seemed fairly fine, until they weren’t. Alwyn, a largely unknown actor at the time, started dating Swift in 2016 amid her drama with Kanye West and Kim Kardashian, when her reputation was at her lowest. They kept a low profile throughout their over-six-year relationship.
While neither publicly spoke about why their relationship ended, some fans believe Alwyn didn’t enjoy Taylor’s larger-than-life persona, and would’ve preferred she kept a low-key profile. Alas, she wanted to be “Bejeweled,” and fans speculate several songs off 2022’s Midnights are about him. The Tortured Poets Department seems to have spared the gory details and focused on Matty Healy. Joe is speculated to have inspired the gut-wrenching track five, “So Long, London,” though, and that’s pretty damning.
6. Joe Jonas
Joe Jonas and Taylor Swift briefly dated in 2009, a relationship which ended with him breaking up with her on a 30-second call. Swift embarked on a smear campaign that she regretted later. They eventually got over it and became friends and started hanging out, with Swift even alluding to her sending him baby gifts in “Invisible String.” Now she’s closer to his ex-wife Sophie Turner, so they might not be on good terms.
5. Harry Styles
The pairing that got us bops like “Out of the Woods,” “Is It Over Now,” and “Style” was none other than Taylor Swift and Harry Styles. The romance was brief but intense, as revealed in the vault tracks from 1989 (Taylor’s Version). The two of them reportedly broke up on vacation after a short romance, but they were seen speaking at the 2021 Grammy Awards and catching up, so they look like they got over whatever drama there was.
4. Conor Kennedy
Taylor dated Conor Kennedy briefly in the summer of 2012, in between her romances with Jake Gyllenhaal and Harry Styles. The breakup wasn’t dramatic and seemed to have run its course, but Swift reportedly wrote “Begin Again” about their short-lived romance.
3. Tom Hiddleston
Taylor and Tom Hiddleston dated briefly in 2016, and it seemed to be the wrong person, at the wrong time. They gave us the iconic Rome vacation, the I heart TS T-shirt, and the adorable MET Gala dance, but for Taylor, he was just the “Getaway Car,” and it didn’t last. He is still one of her best exes and was always respectful to her.
2. Taylor Lautner
The absolute best Taylor Swift ex is Taylor Lautner. They dated briefly in 2010, and he was the muse for “Back to December.” Taylor was always there for her and they reunited in 2023 to film “I Can See You Now,” to the delight of Lautner’s wife, Tay Lautner.
1. Travis Kelce
Taylor and Travis started dating in July 2023, and it seems to be the best relationship she’s ever had. The two have been publicly supporting each other since the beginning. With many insiders claiming this is “The One” for both of them, Travis doesn’t seem to be the least affected by her megastar status and cherishes her the way he should. We stan this, and believe in the rom-com that is Tayvis.
