A petty little ranking of every Taylor Swift boyfriend

Somehow Matty Healy isn’t actually the worst

I love Taylor Swift for her music – obviously. She is The Beatles of my generation, one of if not THEE best songwriter in the industry and a pop juggernaut who’s defined so much of the culture for my entire lifetime. When you’re that famous, of course there is going to be a vested interest in your love life – especially when that love life ends up heavily influencing the songs that then change all of our lives. With that in mind, and nothing else, here is my petty little ranked rundown of all 15 Taylor Swift boyfriends from unforgivable mistakes to the holy trinity of lovely.

16. Sam Armstrong

Sam cheated on Taylor Swift and she wrote the banger that is Should’ve Said No in response. Everyone deserves forgiving for silly little cheating moments from absolutely years ago, but Sam spends his time slagging Taylor off on Twitter to this day. Pack it in, fella.

15. Jake Gyllenhaal

The man whose behaviour caused Taylor Swift to write the most devastating 10 minute song of all time. You watch the short film for All Too Well and tell me if we deserve to wish the best on this man. Great actor, abysmal boyfriend.

14. Jordan Alford

Aka, the subject of Picture To Burn. A redneck heartbreaker who’s really bad at lying? Enough said.

13. John Mayer

Via Richard Isaac/Shutterstock

Thanks to heartbreak caused by John Mayer, we were blessed with the likes of The Story of Us, I Knew You Were Trouble and, ahem… Dear John. Wow lyrical destruction aside, he’s got the energy of a romcom villain and I must loathe him in a pants-esque way. A Big Brother eviction crowd mass boo sort of way.

12. Joe Jonas

I’m Team Taylor and I’m Team Sophie. I’m Team I Don’t Forget The Lyrics of Mr Perfectly Fine. Boo, tomato, tomato.

11. Matty Healy

Oh, the world was in the trenches. Just as Matty Healy was at his most cancelled, Taylor’s having a post-Alwyn fling with him. Thankfully, it only lasted a month or so and never even got officially confirmed so she mostly emerged unscathed. Praise be.

10. Tom Hiddleston

Taylor Swift boyfriends ranked

Via Broadimage/Shutterstock

An off-duty airport slay from Taylor Swift in the above, but yeah, Tom Hiddleston was one of the few month long, inconsequential boyfriends of all the fellas ranked here. We allegedly got Getaway Car and Midnight Rain out of it and I’ve always been quite partial to him as an actor as long as he’s not titting about in the MCU.

9. Connor Kennedy

A couple of Red bops came from Taylor’s dalliance with Connor Kennedy, of the Kennedys. Yes, JFK and RFK Kennnedys. Namely, Begin Again and Starlight – which was written about Robert and Ethel Kennedy, apparently. Scraping into the top 10 on namedropping merit alone.

8. Cory Monteith

RIP, king. It’s sending me that Taylor Swift and Lea Michele share an ex. Wonder if Lea has ever read the lyrics to Mine, allegedly about him. What am I saying! She can’t read, so of course she hasn’t.

7. Calvin Harris

There’s a deep evil to Calvin Harris in the context of getting Taylor Swift boyfriends ranked, but it did result in This Is What You Came For and those not-so-secret Taylor backing vocals left on the track. A bit of an iconic era. If you search This Is What You Came For on YouTube, the Taylor Swift demo is more searched than the actual version with Rihanna. Mad.

Laughing remembering when it came out with the co-writer “Nils Sjöberg” – later revealed to be Taylor Swift.

6. Drew Dunlap

The first of all the Taylor Swift boyfriends we have on record. We wish Drew Dunlap well. They broke up because Drew was off to college – no bad blood, and she wrote Tim McGraw about him. Taylor told USA Weekly “he bought Taylor Swift [the album] and said he really loved it, which is sweet. His current girlfriend isn’t too pleased with it, though.”

5. Lucas Till

Taylor Swift boyfriends ranked

Taylor met Lucas Till when the two were doing the Hannah Montana movie, and there’s no bad blood (pun intended) at all – we love to hear it. He’s a good egg, Ar Lucas. He said of the split “”There was no friction because we were too nice. We just really both liked each other … most relationships work out ’cause you get along and then you don’t, and then you make up and it’s passionate, and with us, I really just liked her as a friend. That’s the only reason that didn’t work out.”

4. Joe Alwyn

Aw, Joe. This one is actually sad because I really thought they were each other’s soulmate. So many besotted Swift songs are about Joe, and he has writing credits on Folklore and Evermore AND Midnights. I hope he’s doing okay. Must be grim seeing Taylor’s Healy era followed straight by her current loved up era.

3. Harry Styles

Via Startraks/Shutterstock

What an era. A pop culture collapse. Taylor Swift wrote some of her best songs about Harry including Clean, Out of the Woods and OF COURSE Style. All that and they’re on good terms and he’s making bangers in his own right? God tier.

2. Taylor Lautner

Taylor Squared wasn’t the best of relationships, but their friendship makes it all worthwhile. It’s so healthy and nice, so pleased they’ve managed to stay on good terms and I literally cherish him being in the I Can See You video so much.

1. Travis Kelce

How can someone making Taylor Swift so happy be anywhere other than the top spot when it comes to getting her boyfriends ranked? This is what she deserves! And he’s the fittest of all time. Every time I see clips of them I feel like I’m watching a film, I need to get a grip.

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