Everything Taylor Swift Has Said About Heartbreak

Taylor Swift has learned her fair share of lessons when it comes to love. Throughout each of Swift's iconic eras, the country-turned-pop star has written songs that don't shy away from tough emotions. Swift's stunning transformation from country balladeer to pop icon came with media scrutiny for her personal life, especially when it came to her highly-publicized relationships. With 11 Grammy wins and scores of hits, the star has broken barriers as a female performer all while staying true to her roots as a vulnerable, poetic, and versatile songwriter.

Her albums — ranging from the alternative Album of the Year winner "Folklore" to her edgy and experimental 2017 comeback album "Reputation" — take on the challenge of embodying emotions like heartbreak, loss, and anger in her music. Now, with two of her re-recorded albums released and more on the way, Swift doesn't seem to mind revisiting those hard feelings alongside her fans. Here's everything you need to know about what she's said about her heartbreaks over the years — and, perhaps more importantly, how to get over them.

In anticipation of the release of her second re-recorded album "Red (Taylor's Version)" in November 2021, Taylor Swift sat down with Jimmy Fallon to discuss what those years behind the versatile album had been like. "I was going through a bit of a sad time," she said. While in band rehearsals for her "Speak Now" tour, Swift found herself strumming four chords and making up lyrics on the spot about what she was going through. "I started playing guitar and the band joined in," she said. "The song just went on for about 10 to 15 minutes." Luckily, Swift's mother nabbed a recording of the impromptu emotional jam session from the sound guy. The song went on to become one of the singer's most iconic break-up ballads, "All Too Well."

Fallon asked the 32-year-old if she often found herself using songwriting to work through emotions, and what other mediums she uses to process difficult times. "I do all of that," she said, saying that writing songs, journaling, and talking to her mom are necessary parts of getting past rough relationships. "I journal, I talk to my friends, I write songs, I buy cats," she said. "If you're going through a hard time, [cats] are very understanding."

Working through your emotions can lead you to a magical moment of liberation, as Taylor Swift once said. In a 2015 interview with "Elle," the Pennsylvania native talked about the meaning behind her "1989" track "Clean." She told the outlet, "Someone I used to date — it hit me that I'd been in the same city as him for two weeks and I hadn't thought about it. When it did hit me, it was like, 'Oh, I hope he's doing well.' And nothing else."

That acceptance is a stark difference from the heavy weight of heartbreak. As Swift said, "A heartbroken person is unlike any other person. Their time moves at a completely different pace than ours. It's this mental, physical, emotional ache and feeling so conflicted. Nothing distracts you from it. Then time passes, and the more you live your life and create new habits, you get used to not having a text message every morning saying, 'Hello, beautiful. Good morning.'"

Finding new routines is vital for reaching that independence, according to the Grammy-winning singer. "You replace these old habits with new habits, like texting your friends in a group chat all day and planning fun dinner parties and going out on adventures with your girlfriends, and then all of a sudden one day you're in London and you realize you've been in the same place as your ex for two weeks and you're fine."

As Taylor Swift climbed the mountain of success, she realized that she might want a long-term partner to soak in the view alongside her, something past lovers hadn't provided. In the 2020 Netflix documentary "Miss Americana," Swift recounted winning Album of the Year for her pop sensation "1989," and how she wondered what it'd be like to have someone beside her at that moment.

"I had won Album of the Year at the Grammys for the second time, which I didn't think was a possibility," she said. "And I remember thinking, 'Oh, my God, that was all you wanted' ... That was all you focused on ... You get to the mountaintop and look around and you're like, 'Oh, God. What now?'" She added, "I didn't have a partner that I climbed it with that I could high-five. I didn't have anyone I could talk to who could relate to what I was [going through] ... I just wondered, 'Shouldn't I have someone that I would call right now?'"

That loneliness changed between the release of "1989" and "Reputation." During her stint away from the media — following her highly publicized feud with Kim Kardashian and Kanye West — Swift found herself in a wholesome, private relationship. The "I Knew You Were Trouble" singer and British actor Joe Alwyn have been together since 2016, according to Page Six. When she won AOTY a third time in 2021, she had someone at the mountaintop with her.

One of the most memorable Taylor Swift performances is also one of the most heart-wrenching to watch. At the 2014 Grammys, Swift performed the song "All Too Well." Her voice was shaky with emotions and her eyes were welling with tears, but the performance is proof that the "Cardigan" singer is no stranger to heartbreak.

Her single, "All Too Well," has lived many lives as a song, according to Swift herself. While it was once one of the most difficult and emotional songs for her to perform, she's since shared that her fans have replaced those sad memories with images of them screaming the words alongside her at live performances. As she strums her guitar before performing the "Red" track on the 2018 "Reputation Stadium Tour" film, Swift gives a speech dedicated to her "Swifties."

"This song has two lives to it in my brain. In my brain, there's the life of this song where [it] was born out of catharsis and venting and trying to get over something," she said. "And then there's the life where it went out into the world and you turned [it] into something completely different for me. You turned it into a collage of memories of watching you scream the words to this song."

Swift aptly and emotionally added, "And that is how you changed the song 'All Too Well' for me."

It seems that Taylor Swift doesn't spend as much time remembering her exes "All Too Well" anymore. In an interview with Seth Meyers before the release of "Red (Taylor's Version)," the comedian asked if she thought about what the re-release would be like for those heartbreakers of long ago. "I wonder if there are people who might think that they were the one you were singing about, if it's easier or far, far worse for them 10 years later," Meyers mused.

"I haven't thought about their experience, honestly," Swift said with a light laugh. "I think that's the biggest burn," Meyers went on, with the crowd cheering at Swift's nonchalance. "I think there's nothing they'd rather hear less right now," he said. As she sang on the opening track of her seventh album "Lover," it seems she simply "forgot that you existed."