13 Favorite Taylor Swift Songs & Why

For awhile I had wanted to sit down and pick out my 13 favorite Taylor Swift songs. I really wanted it to be somewhat of a therapeutic experience where I could just sit around my apartment with a journal listening to her music, while simultaneously sipping some passion fruit tea. During the process so many memories and emotions came flooding back. I thought about the songs that I belted out in the car in high school. I thought about the songs I danced to in the wee hours of the morning with my bestie and made silly music videos to. I thought about the songs that carried me through a broken heart and the songs that helped me heal it again. Much of her music has become the backdrop throughout each chapter of my life, and honestly, it's hard to imagine a time before these songs existed.

13 Favorite Taylor Swift Songs & Why

13. THE BEST DAY | Fearless

Favorite Lyric: "I know you were on my side, even when I was wrong"

I remember listening to this song on my way home from my high school scholarship awards ceremony. It was just my mom and I in the car. I remember telling her that it reminded me of us and since that day it has been loosely considered "our song." I can't help but smile and think of her each time I hear it.

Mom & I the scholarship awards ceremony, May 2010

12. TIM MCGRAW | Taylor Swift

Favorite Lyric: "When you think Tim McGraw, I hope you think of me"

This is the very first Taylor Swift song I ever heard and I fell in love with it right away. Every time I hear it, I am transported back in time. Suddenly it's 2006 and I'm just a small town girl living in a rural Wisconsin town. Ah, simpler times.

11. 22 | Red

Favorite Lyric: "Everything will be alright if we just keep dancing like we’re 22"

If any song sparks joy, 22 is it. I think it's one of the best songs you can dance to and sing into your hairbrush as you get ready. The single for 22 was brand new and very popular when my 21st birthday rolled around. I remember dancing at the bar with a fruity drink in my hand surrounded by my besties. Could a girl dream up a better birthday celebration?

And of course I wore a sparkly red dress!

10. I KNEW YOU WERE TROUBLE | Red

Favorite Lyric: "He was long gone when he met me, and I realize the joke is on me"

Most people assume this song is just the typical "good girl falling for bad boy" scenario, but to me, this song is about the tragedy of losing yourself in a relationship. A tragedy that happens when you ignore the red flags and end up giving up so much, only to realize in the end that the person doesn't even care about you.

Relationship boundaries were something I really struggled to establish. I used to ignore all types of red flags and I used to accept being someone's "backup plan." I used to think, "If I'm nice, and if I try to do the right thing, you know, they'll see my value. If I just try hard enough, maybe I can make them happy enough to treat me well." And it turns out I can't. During this phase I was a bit of a wreck and had a lot of learning to do, but I am thankful for that time in my life now because I came back stronger and wiser on the other side.

9. FIFTEEN | Fearless

Favorite Lyric: "When all you wanted was to be wanted, wish you could go back and tell yourself what you know now"

Fifteen is such a special and meaningful song to me because it's the sisterly advice I needed to hear while I navigated high school. This song that taught me the world is bigger than the hallways of high school. I hope that if I am lucky enough to have kids someday, that they get to hear songs like this that help put the naive, confusing high school years into perspective. Because we all know that even though talks from mom & dad are well intended, they aren't as easily received by teenagers as meaningful lyrics are.

8. BLANK SPACE | 1989

Favorite Lyric: "Darling I'm a nightmare dressed like a daydream"

Admittedly I am obsessed with this music video and applaud the meaning behind this song. I just love the sassy cynicism of Blank Space and how she mocks the media's perceptions of her. I also feel like I can relate to the “psycho girlfriend” she plays in the Blank Space music video on a deep, personal level. Not because I have ever smashed a guy's sports car with a golf club or anything, but I have definitely had my emotions discredited. I've been called crazy, needy and dramatic in situations where I was simply trying to communicate the depth and complexity of my emotions. 🙃 It's comforting to know I'm not the only one.

7. STYLE | 1989

Favorite Lyric: "You got that James Dean daydream look in your eye, and I got that red lip, classic thing that you like"

Style is one song that makes in onto nearly every playlist I've created. It's a Swift jam for the ages, it's catchy, it's edgy, it's pure GOLD. ✨

6. LOVE STORY | Fearless

Favorite Lyric: "Is this in my head, I don't know what to think, he knelt to the ground and pulled out a ring and said.."

Love Story was the first music video I ever purchased from iTunes. I am not exaggerating in the slightest when I say this, but very single day while I waited for the school bus, I watched the masterpiece that is the Love Story music video on my purple iPod Nano. Sixteen-year-old me was utterly obsessed with this song; a hopelessly romantic tale of teenage love. Can you blame me? Love Story was practically a 4 minute long Disney movie!

Just trying to channel Tay's Love Story vibe for Prom 2009..

5. DELICATE | Reputation

Favorite Lyric: "Long night with your hands up in my hair, echos of your footsteps on the stairs, stay here honey I don't want to share... 'cause I like you"

This is my most beloved song from the Reputation era. If you watch the Delicate music video, she starts off zoned out, simply going through the motions of her life. Once she's alone and invisible to the rest of the world, all the pressure and expectations melt away and she is free to be who she really is! She makes silly faces at herself in the mirror and then she dances onto a street in the pouring rain, as if she’s reenacting Singin’ in the Rain, and she’s never looked happier! By the end she's danced away her troubles and found a new inner peace.

Now each time I hear Delicate I just want to play it loud and proud and humble myself with some awkward dancing. After all, life is all about randomly bursting into dance and living in the moment... Isn’t it? Isn’t it? Isn’t it?... 😏

4. LAST KISS | Speak Now

Favorite Lyric: "All that I know is I don't know how to be something you miss"

Last Kiss is definitely one of Tay's darker songs. After going through a gut-wrenching breakup I had a mess of tangled emotions to work through. I was a bit of a wreck (ok, maybe a major wreck) and I swear I listened to this song daily and cried both happy and sad tears just to move on mentally.

3. ENCHANTED | Speak Now

Favorite Lyric: "Please don't be in love with someone else, please don't have somebody waiting on you"

Ahhhh.. the butterflies and an indescribable spark. Enchanted is a beautiful song about that magical moment when you first meet someone. My favorite part of this song is a really raw part in the bridge where you *think* the song has come to a natural conclusion.. but then she quietly pleads: "please don't be in love with someone else, please don't have somebody waiting on you." Oof, when I hear that line my heart breaks for 18-year-old Joy who once cried alone in her room, believing that she wasn't good enough for a boy who did horrible things to hurt her.

Speak Now release day, October 25, 2010.

Right after I dragged my college roommie to Target with me :)

2. ALL TOO WELL | Red

Favorite Lyric: "You call me up again just to break me like a promise, so casually cruel in the name of being honest"

All nostalgic, all bittersweet, All Too Well is Taylor Swift at her absolute best. Truthfully, this song rips me apart. It reminds me of someone I couldn't let go because my world just didn't make sense without him in it. When you go through a loss that's so deep, it's impossible to avoid the storm of desperate, helpless feelings that follow. For years, I was still angry, confused, and absolutely devastated by the grief of losing this person and all the memories and hopes for the future. When I hear All Too Well I can feel what it was like for me to be in that place.

1. LOVER | Lover

Favorite Lyric: "My hearts been borrowed and yours has been blue, all's well that ends well to end up with you"

I know that All Too Well is widely considered Tay's magnum opus but I already know that Lover has earned its place among my 13 favorite T.S. songs ever. Why? Because it's truly a timeless love song. So timeless, I guarantee you'll hear it being played at weddings in 20 seconds and 20 years from now.. 😉

Lover is stripped down ballad that isn't built on metaphors, fantasies, or fears - it's about the seemingly insignificant things that encompass what real, deep love is. Love that is built on mutual respect, honesty and shared values. It's about the person who will show up for you when you need them and care for you even after they've seen you broken. A genuine friendship that's blossomed into love; the type of love I truly hope to find someday.