11 Phases of My Life Told Through Taylor Swift Album Releases

“Taylor Swift” all the way through “Red (Taylor’s Version).”

I’ve never been the kind of person who follows artists religiously. Someone who listens to every album right at midnight, who buys tickets for every tour, who knows all the details about the artist’s career and personal life, who considers themselves a fan in every sense of the word. I’m a passionate person, but that's not usually the way it comes out for me. My admiration is quieter and directed from the sidelines instead of front and center. I guess sometimes that makes me feel inadequate. Like I’ll never love an artist as much as other people do. There really isn’t an artist I feel is truly mine.

Except for Taylor Swift. And honestly, that happened mostly by accident.

Taylor Swift is a year older than me, so when she first started releasing music, we were peers, two high school kids just trying to find their way through it. My best friend then who’s still my best friend now introduced me to her. You’ve gotta check her out, he told me, and I quietly fell in love.

Artists don’t often stick to me the way they do to other people, and that’s not really what happened this time either. Instead, we grew together. For each phase of my life, Taylor was there with a new album to offer insight into everything I was going through. As I grew, so did she. We both became better writers. We both picked partners, some good and some bad. We were both shattered, and then learned to pick up the pieces. Whether I wanted her to or not, Taylor Swift shaped and narrated the different stages of my life.

For every phase of my life, there’s a story. A string of memories. Triggering smells and feelings. And a Taylor Swift album to pull it all together. There are so many songs from each album that helped me get through the things I was enduring. For brevity’s sake, I’ve chosen just one to represent each phase.

It may seem silly, but these words mean so much. Then, now, and forever.

Taylor Swift (Oct. 2006)

I’m only up when you’re not down Don’t wanna fly if you’re still on the ground It’s like no matter what I do Well, you drive me crazy half the time The other half I’m only trying To let you know that what I feel is true And I’m only me when I’m with you

- I’m Only Me When I’m With You, Taylor Swift

For her first collection, Taylor wrote about romantic love, but I wasn’t there yet. I thought I was, I’m sure. I had crushes, but nothing tangible. I was still a baby in a teenager's body and didn’t truly understand romantic love. What I did understand, though, was friend love.

My best friend introduced me to Taylor Swift, an artist that has stuck with me for over a decade and a half now, because he knew I’d connect with her. He knew me, and he knows me, and back then that was everything. It’s still everything. Taylor may have been writing about boys, or maybe she wasn’t, but either way, her lyrics were the narration of my best friend and I, two kids in a small town, listening to music in the car and hanging out in diners and yelling about all the feelings we didn’t understand yet. Just two teenagers listening to Taylor Swift together and hoping we’d be best friends forever. It’s been two decades now, so I like our chances.

That was the beginning of my Taylor Swift love affair, and I wouldn’t want to have started it any other way.

Fearless (Nov. 2008)

And I don’t know how it gets better than this You take my hand and drag me head first Fearless

- Fearless, Taylor Swift

And then, I fell in love. For the very first time, the lyrics of the love songs all made sense, or as much sense as anything can to a high school kid. I started dating my first boyfriend in March of 2008, and by November, we were completely head over heels for each other. I really didn’t know how it got better than that. I didn’t think it would. He was it for me, and I knew Taylor would understand better than anyone.

We met at boarding school, and together we took full advantage of the freedom that comes with not living at home. “Fearless” makes me think of the day we got permission to leave campus and go on a mini-adventure. Biking down the road to a state park, having a picnic in the woods, exploring each other in an abandoned train tunnel. We were fearless together, just like our love was, too. I guess that’s always how it goes. Young love is fearless because you’ve never done it before. You haven’t been hurt yet, so you jump in with both feet and hope for the best.

Speak Now (Oct. 2010)

It turns out freedom ain’t nothin’ but missin’ you

- Back To December, Taylor Swift

We broke up in October of 2009, and I let all of Taylor’s heartbreak songs carry me through. By the fall of 2010 I was past it, and suddenly experiencing a whole new kind of heartbreak — change. I’d graduated from high school and left my tiny, safe boarding school in the middle of nowhere Connecticut, and headed off to college in the heart of Boston. When Speak Now came out, I used it to drown out all of the feelings I hadn’t processed yet. I would walk circles around the Boston Common, “Back to December” blasting through my headphones, and try to enjoy my newfound freedom when all I really wanted was to go back to the way things were.

I hadn’t been ready to grow up and move on yet. I’d found comfort and confidence at my boarding school at a time in my life when I never thought that was possible. It had helped me grow into the person I’d always wanted to be, and it wasn’t until after I’d left that I realized I hadn’t been ready to leave.

But with each day, and each lyric, things got easier. Taylor Swift sang comforts into my ears as I walked around the Common and learned to love my new life.

Red (Oct. 2012)

And I might be okay but I’m not fine at all

- All Too Well, Taylor Swift

As I moved through my college journey, I settled into Boston, but I don’t think I ever really found myself there. I loved Boston and I always will, but I hadn’t met the right people or done the right work or I just wasn’t ready yet. It most likely had a lot to do with the fact that I didn’t truly love myself yet. Whatever it was, something was off. On the outside, I looked ok. On the inside, I was really struggling.

When Red came out, I was living off-campus in an apartment in Cambridge. I had friends and jobs and school and a life — but none of it had really clicked yet. I was on the edge of me, but I wasn’t quite there yet.

I walked through the streets of Cambridge, from Central Square to Harvard Square, feeling lost and a little broken and allowing Taylor to help me try and piece it all together.

1989 (Oct. 2014)

When we first dropped our bags on apartment floors Took our broken hearts, put them in a drawer Everybody here was someone else before

- Welcome To New York, Taylor Swift

1989 felt like a huge shift from Taylor Swift. It was a different feel and a different vibe, and, of course, so was my life. I had graduated college and moved down to Florida to do the Disney College Program. I was living and working with 7,000 other college students and recent grads from all over the country and the world. In a lot of ways, we were all just a bunch of misfits who had come to Disney hoping to find belonging, in both the work and each other. And for me, I did. I think for the first time since boarding school I finally felt like I was in the right place at the right time, and I leaned into it with all I had.

Of course, there were hard moments. There always are. It wasn’t an easy experience in the least, but it still always felt right. I made incredible friends and didn’t feel awkward interacting with my peers the way I often had in college. We were all a little quirky, I guess, and those are the kind of people I thrive around. It was hard, but it was worth it. That kind of felt like the vibe of 1989, too.

I’d sit on the bus on my way to work, listening to “Welcome To New York” and thinking how it all still applied, even though I was in Florida. In June 2015, I moved to New York City and I took the song with me, grateful for the sentiment and eager to see what the next phase would hold.

Reputation (Nov. 2017)

Don’t pretend it’s such a mystery Think about the place where you first met me

- Getaway Car, Taylor Swift

When Reputation first came out, I didn’t listen to it. It was the first time I hadn’t listened to an album that Taylor put out. I heard one of the singles and saw the music video and I just … didn’t get it. I didn’t connect to it. I felt lost, and that wasn’t usually how I felt when Taylor’s music started to flow. It made me uncomfortable. It made me a little sad.

It was just so different from what I was used to, and I guess I felt betrayed. It felt like I didn’t really know something that had been such a huge part of my life as well as I thought I did. Really though, the artist I loved was just figuring herself out — and so was I.

Reputation made me uncomfortable because I was in a phase of trying to figure myself out, too. A lot was happening in my life. I had moved across the country to Los Angeles, I was trapped in an abusive dynamic without realizing it, and I was coming to terms with the fact that I was non-monogamous and trying to figure out how to navigate that. Who I was becoming hadn’t yet caught up with how I was living my life.

I finally listened to Reputation years after it came out, and it didn’t make me feel uncomfortable, because I was finally ready to hear it.

Lover (Aug. 2019)

Said I’m fine, but it wasn’t true I don’t wanna keep secrets just to keep you

- Cruel Summer, Taylor Swift

When Lover came out, I needed it so bad. I was making all the wrong choices when it came to love, and even though I know it wasn’t always my fault, it’s still hard to look back on. “Cruel Summer” hit me like a train. I listened to the lyrics and tucked them away, and they pulsed in my subconscious until I was finally able to hear them for what they were.

I was lost and yet at the same time was finally growing comfortable with who I was meant to be, and the vibe of Lover felt a lot like that to me, too. It felt like maybe Taylor had found her groove. It felt like coming home. Painful sometimes but also beautiful.

Lover felt like Taylor continuing to find herself, and I knew that’s what was happening to me too.

Folklore (Jul. 2020)

I think I’ve seen this film before And I didn’t like the ending I’m not your problem anymore So who am I offending now?

- Exile (Feat. Bon Iver), Taylor Swift

To me, it feels like the theme of 2020 was “we can’t go on like this.” It was the year we realized things needed to change. The pandemic forced it upon us, giving us all too much time to sit alone and think and watch. 2020 was so hard, but it was also so transformative.

I realized I didn’t want to go back. I didn’t want to repeat the same patterns. I wanted to give myself everything I deserved. When Folklore came out, I was still very much in the midst of that process, and having a new Taylor Swift album to listen to as I moved through my feelings was so helpful and therapeutic.

Evermore (Dec. 2020)

There’ll be happiness after you But there was happiness because of you Both of these things can be true There is happiness

- Happiness, Taylor Swift

Getting two Taylor Swift albums in the same year felt like such a gift, and I didn’t take it for granted. “Happiness” definitely hit me the hardest because it felt like it applied in so many ways. There’ll be happiness after the pandemic, after the abusive relationship I finally got myself out of, after all sorts of things that were no longer serving me, and there was happiness because of all of that, too. Sometimes that felt heavy, that the things that hurt me could also make me happy at the same time. Feelings aren’t linear, though, and this song helped remind me of that.

Listening to Evermore, it baffled me that a decade and a half later, the same artist's lyrics could still apply so heavily to my life and help me so much. Taylor had grown and so had I, and I found so much comfort in that.

Fearless (Taylor’s Version) (Apr. 2021)

Goodbye, Mr. “Casually cruel” Mr. “Everything revolves around you” I’ve been Miss Misery for the last time And you’re Mr. “Perfectly fine”

- Mr. Perfectly Fine, Taylor Swift

Fearless (Taylor’s Version) threw me back into the past but in a good way. I got to listen to reboots of songs I’ve always loved and think about the old versions and the old version of me who listened to them. The new versions flowed through the new version of me and I couldn’t help but smile. The songs I’d never heard before still fit the theme, and I tried to listen to them both through the mindset of the new me and the old me.

If a younger version of myself had listened to Mr. Perfectly Fine, there would likely be a lot of resentment. Instead, there was clarity, awareness, and a little sadness. I’d learned my lesson and I wasn’t looking back.

Some people may think re-releasing old albums is silly or self-indulgent. I personally think it’s such a gift for all the listeners, and I’m sure for the artist, too.

Red (Taylor’s Version)

The idea you had of me, who was she?

- All Too Well (10 Minute Version) (Taylor’s Version)

When Red (Taylor’s Version) came out, I was having a bad night. I felt like I was drowning under the weight of everything I’ve been dealing with lately. I was supposed to go over to a friend’s place for a listening party, but as I put on my red pajamas and got ready to head over, I realized I just couldn’t do it — and that was ok. Instead, I climbed into bed and I let Red (Taylor’s Version) calm me down. I let the lyrics soothe me the way they always had. Listening to it didn’t fix anything, but it made me feel less alone, and there are few things in life more valuable than that.

When Red first came out, I was going through a rough time in my life, and now with this rerelease, here we are again. I guess that’s life, right? Nothing is linear. We take life as it comes. That’s what I’ve always done, and judging by her songs, that’s what Taylor has always done, too.

I’ve never known a lot about Taylor’s personal life. I don’t follow all of the celebrity gossip. I try not to make assumptions about who she is. All I know is what her lyrics tell me, and the way they make me feel as I navigate some of life’s toughest moments. No one is ever exactly the way the world thinks we are. We don’t always get to do life exactly the way we want to. Sometimes we get redos, and sometimes we don’t. Taylor Swift is just another person trying their best, and that’s what I’ve heard year after year, album after album, blasting into my ears as I walk around the world. Someone else going through life’s challenges, trying to remind me that I’m not alone.

I’m grateful for this artist who I’ve grown alongside. I’m grateful for her journey and I’m grateful for mine. When I’m 40, 60, 80, I’ll still be listening to her words, still finding comfort in them, and still just trying my best.