You’d be hard pressed to find a celebrity more entrenched in the zeitgeist right now than the almighty Taylor Swift. With her approachable ease that doesn’t come off haughty or disconnected, and her easy- to-remember melodies and songs, it’s understandable on pretty much every level why she’s so famous.
It’s a fame that seems to inspire a dedication seemingly reserved for The Beatles or Eminem in his prime, but it also has what seems like its own identity. Swift is a once-in-a-generation talent and performer, and within that sphere it’s easy to forget she’s also just a person like you and me.
I mean, a very, very talented and wealthy person who can’t even go to a grocery store without being mobbed by teens, but a person nonetheless. Just like any of us, she dates and falls in and out of love.
The difference is, of course, the fame means that people are interested. Her fans are invested in her life and they want to know who she’s dating, when and for how long. The other side of that coin is she’s so famous she can pretty much date whoever the heck she wants.
Honestly, who wouldn’t want to date one of the world’s most famous women? I bet even my mom would at least give it a thought. Because of this, TaylorvSwift has quite the rolodex of famous beaus, from the crooning John Mayer to the brooding Taylor Lautner to the presidential Conor Kennedy.
It can be hard to keep track, right? No worries, I got you. Here’s an exhaustive list of America’s favorite musician’s boyfriend history. Disclaimer: Swift has had a lot of boyfriends, and I am a journalist and not a Swiftie. We will update this exhaustive piece if we miss something, but there is a lot of information out there about this and not all of it is the same. Cut me some slack please, (aka don’t DM me).
Brandon Borello
Borello is an early piece of Swift legend. The two apparently dated in high school and he was reportedly the one who inspired the classic Swift tune “Tim McGraw.” Say what you will, Swift knows how to put words together. Check out these lyrics:
“Just a boy in a Chevy truck
That had a tendency of gettin’ stuck
On backroads at night
And I was right there beside him all summer long
And then the time we woke up to find that summer gone”
Unrequited love! Romance! It’s got it all. How weird would it be for the most momentous thing you do in your life is date one of the world’s most famous pop stars before they were famous? You were so close, Borello! Who knew that going away to college was such a bad idea?
Jordan Alford
Alford also is a little footnote in the Swift pre-fame years. He supposedly inspired the song “Picture to Burn,” and the two attended Hendersonville High School together in Tennessee. Alford apparently left her for a classmate named Chelsea.
Alford and Chelsea later married, and Chelsea told Daily Mail that she was friends with Swift until Alford came between them.
‘We were kind of good friends at school, later not so much. She dated him, that’s why,” she said. I wonder if he regrets it. It kind of feels like that moment in Indiana Jones when the Nazi dude picks the wrong cup.
Drew Hardwick
Hardwick has the distinction of apparently inspiring Swift’s breakout hit “Teardrops on My Guitar.” She’s gone on record saying that Hardwick is a real person. Here’s some irony: Hardwick didn’t even know she was into him!
Swift shared that two years after the song came out he showed up at her home and asked her on a date. Too little too late, Hardwick! It’s for the best, though, because he was arrested on charges of child abuse back in 2015.
Sam Armstrong
There’s a theme developing here, and that theme is that people seem to cheat on Swift. Add Sam Armstrong to that list. It’s not a total loss, though, because we got the song “Should’ve Said No” out of it.
In her CD booklet for her first album, she capitalized every S, A, and M in the correct order. Woof. Armstrong seems to have taken a more confrontational approach about the whole thing, and trashes Swift on social media. And not just social media, he went on a talk show! That video is above. Other songs are understandably about him as well.
How about this comment on the aforementioned video: “I cannot fathom how a person could ever cheat. ESPECIALLY ON TAY??? SHE WAS LITERALLY A GORGEOUS COUNTRY BARBIE DOLL?!??”
I mean, cheating is crappy no matter how you spin it, but sure.
Joe Jonas
Ok, now we’re getting into the fame years. The majority of boyfriends from here on out are people pretty well-known and don’t need that much explaining. Joe Jonas is one of the Jonas Brothers, a popular boy band from the 2000s and beyond.
Jonas apparently broke up with her on a 30-second phone call, something she bemoaned on an episode of The Ellen DeGeneres Show. Better than a text, to be honest, as we’ll see later.
Songs about Jonas include “Forever & Always” and “Last Kiss.” “Better Than Revenge” is reportedly about his ex, Camilla Belle.
Lucas Till
Swift dated then Hannah Montana star Lucas Till briefly after Jonas. They ended their romance amicably and became friends. He even appeared in the “You Belong With Me” video. He told MTV he just liked her more as a friend.
“We dated for a little bit. But, there was no friction because we were too nice. We just really both liked each other … [but] most relationships work out cause you get along and then you don’t, and then you make up and its passionate, and with us I really just liked her as a friend. That’s the only reason that didn’t work out.”
That’s a very mature way of looking at things. Not all of her relationships end this sweetly. He’s doing fine, by the way.
Taylor Lautner
Lautner was one of the hottest heartthrobs on earth back in the day, especially after he appeared in the Twilight movies. The two started dating after they met on the set of the movie Valentine’s Day. Apparently he was more into her than she was into him, and the song “Back to December” is thought to be an apology song to him. These lyrics:
“You gave me roses, and I left them there to die… So this is me swallowing my pride, standing in front of you saying I’m sorry for that night… You gave me all your love and all I gave you was goodbye.”
They broke up in 2010.
John Mayer
Firstly, no one should feel bad for John Mayer. He has quite the dating history himself, and it’s perhaps inevitable that these two incredibly talented and famous humans got together.
What’s pretty crazy is that like Lautner, she apparently broke it off with Mayer, so much so that he wrote a song about her, called “Paper Dolls.” But we’re not here to talk about Mayer. The song “Dear John” is definitely about him and “Ours”, “Superman”, “The Story of Us”, “I Knew You Were Trouble” and “Would’ve, Could’ve, Should’ve” are all rumored to be.
Cory Monteith
RIP Cory. This is a sad one because of what happened to Monteith back in 2013, but the couple apparently dated very briefly and unofficially in 2010. She was asked about their relationship on Ellen, and she blushed a little when the host brought him up.
When he died she tweeted: “Speechless. And for the worst reason.”
The song “Mine” is rumored to be about him.
Adam Young
Adam Young is more of a footnote than an ex. He’s the guy from that annoying band Owl City who wrote that song about hugging fireflies. The song caught Swift’s attention and she wrote “Enchanted” about him.
When he finally made his move, as is the Swift way, she was already on to another. Too bad, Adam, go be with your insects.
Jake Gyllenhaal
Gyllenhaal holds the distinction of being one of the few (maybe the only) person to break up with Swift through text. In the beginning, he pulled out all of the stops for her. He spent $160k on a private jet for a date (man, it must be great to be rich).
The rumor is that Gyllenhaal couldn’t get past their 10-year age difference, but that’s a pretty weak excuse. At some point, we have to maybe realize that Swift is maybe terrible at relationships, or she just uses them to write more songs.
She got a bunch out of this one, like the song “All Too Well,” with these lyrics:
“Left my scarf there at your sister’s house. And you’ve still got it in your drawer even now” and “Now you mail back my things and I walk home alone, But you keep my old scarf from that very first week ‘Cause it reminds you of innocence and it smells like me.”
He’s also been seen wearing said scarf, apparently.
Chad Overstreet
Another rumored footnote. This one hasn’t been confirmed, but there’s a picture of them maybe on a date, so he’s making the cut.
Eddie Redmayne and Zac Efron
These two are getting lumped together because neither got a song and some dispute that they actually dated. I’m including them for completionist purposes and because I take my job seriously.
Conor Kennedy
Conor is the grandson of current presidential candidate Robert F. Kennedy (that’s gonna look weird in a few years). They dated in 2012, and in this relationship she was the older one at 22 and Conor was just 18.
She even bought a house near him when they were dating. The song most likely linked to Kennedy is “Begin Again,” with the lyrics: “I think it’s strange that you think I’m funny ’cause he never did.”
Harry Styles
How could these two not have dated? It was inevitable! She apparently wrote “Out of the Woods”, “I Know Places”, “Clean”, “Style”, and “Question…?” about Styles, so no matter how you look at it, that’s a pretty successful relationship. The rumor is that his song “Perfect” is about her.
Calvin Harris
She dated musician Calvin Harris for more than a year! The songs “I Did Something Bad”, “Getaway Car”, “Bejeweled”, and “High Infidelity” are all rumored to be about Harris.
Also the line “But when I walked up to the podium I think that I forgot to say your name” from “coney island” is supposedly a reference to Harris’ 2016 GQ-Men of The Year Awards speech.
Tom Hiddleston
The Loki star dated Swift in 2016. “Getaway Car” and “Midnight Rain” are rumored to be about him. The glare of their relationship in the spotlight reportedly became too much to bear.
Joe Alwyn
These two dated for seven years, her longest relationship to date. The songs “Lover” and “Cornelia Street” are about him.
Matty Healy
This rumored rebound romance didn’t last long at all, as they were rumored to break up last month after dating in May. Healy is the lead singer of the popular band the 1975, by the way.
Who will she date next? Stay tuned!
