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Taylor Swift Songs That Hit So Much Harder Now That I’m In My 20’s

This article is written by a student writer from the Her Campus at CU Boulder chapter.

Taylor Alison Swift: one of the most influential musicians of our generation, a poet in her own right and name. Ever since my childhood, Taylor has been a staple for many women my age. I’d always casually enjoyed her music as it played on the radio when I was young (“Love Story” and “Our Song” were fan favorites in our car), but it wasn’t until I made my way to university that her songs truly began to have a bigger impact on me. I found myself able to relate more deeply to her lyrics: heartbreaking, whimsical compositions about growing up and learning how to navigate the impossibilities of womanhood that society thrusts on us. I never personally felt the impact of her songs until I grew older. But now, freshly in my 20’s, I can confidently say that I do. In honor of the Eras Tour, which felt like a resurgence back to my roots of childlike wonderment and whimsicality in the name of Taylor Swift, here are ten Taylor songs that hit so much harder now that I’m in my 20’s (yes, one from each album). 

“It could stay this simple / and no one’s ever burned you / nothing’s ever left you scarred / and even though you want to / just try to never grow up.” 

Starting off strong with the album “Speak Now (Taylor’s Version)” – and yes, I was absolutely one of the many people who lost her mind when she released her version this summer – I have to go with “Never Grow Up”. This song awakens a nostalgia in me for my childhood. I find myself reminiscing on those cherished moments I shared with my family – those treasured snapshots in time that had felt so inconsequential in the moment. When I was younger, there was this self-imposed rush I placed on myself to grow up and get out on my own. I wanted independence from my family; I wanted to answer only to myself. But now as I navigate life as an adult, I feel an odd sense of longing for the past: a past filled entirely with joy and laughter, where I was not forced to face the harsh realities of this world on my own. 

“Each bar plays our song / nothing has ever felt so wrong / oh my, love is a lie / shit my friends say to get me by / it hits different / it hits different this time.”

From “Midnights (the Til Dawn Edition),” I personally have to pick “Hits Different.” As I go through life, I find that each subsequent break-up I experience hurts more than the last. Be that the fault of experiencing deeper – yet unfortunately fleeting – connections as I grow older, or simply letting myself love too hard, I am entirely unsure. I have always been, in no uncertain terms, a lover girl at heart (I take after my father in that regard). I feel my emotions fiercely, so as a consequence, I love extremely deeply. I learned early on in life that not all others feel things as intensely as I do, so I have had to navigate coping with such intense heartbreak on my own. While it can be difficult, it truly feels like a core component of growing up. 

“How can a person know everything at 18 but nothing at 22? / And will you still want me when I’m nothing new? / How long will it be cute / all this crying in my room / when you can’t blame it on my youth / and roll your eyes with affection?” 

This wouldn’t be a proper list without including “Nothing New (ft. Phoebe Bridgers)” from “Red (Taylor’s Version).” I mean, come on. “How can a person know everything at 18 but nothing at 22?” I have never related harder to a line in my life! I feel as if I am becoming more confused by life’s complexities as I enter my 20’s. Learning how to navigate this world on my own is not an easy task (a notion which, I’m sure many people my age can relate to). Add in the identity of being a woman in today’s society, and life gets all the more difficult. Unfortunately, due to society’s impossible standards, women are desired and tolerated more when we are younger. Our emotions have been historically played off as childlike overreactions: it is common to not be taken seriously. In that regard, I feel like expressing strong emotions was more readily-accepted when I was a girl. People could write off my feelings as a “childlike phase” I had to get past; it was seen as endearing. As I grow older, I am already noticing that expressing strong emotion and not simply maintaining a stoic facade is frowned upon. I worry about the day when I can’t comfortably express that side of myself anymore: a day that I fear is approaching way too soon.   

“And you’re the prettiest lady in the whole wide world […] / I know you were on my side / even when I was wrong […] / staying back and watching me shine and / I didn’t know if you knew / so I’m taking this chance to say / that I had the best day with you today.”

In all honesty, this song was probably my easiest pick. The minute I started on this article, I knew I wanted to write about “The Best Day” off of the album “Fearless (Taylor’s Version).” This song reminds me so much of my mother. In no uncertain terms, she is the most magical person I know. My mother always nourished my childlike wonder when I was young and imparted the importance of wisdom and independence on me. In other words, she let me know that I could be the princess I wanted to be, but I didn’t ever need a prince on a white horse to come in and save me. I idolized my mother when I was a child: I still do. She is literally the prettiest lady to me to this day, both inside and out. She’s always had my back, supported me and advocated for me. She truly taught me what unconditional love looks like. Quite frankly, she is the reason that I am able to dream. All of my best days involved her when I was younger, and a good amount of them still involve her now. My appreciation for my mother grows as I get older. I would have never gotten to where I am today without her guidance and support. 

“Yes I got your letter / yes I’m doing better / I know that it’s over / I don’t need your closure / […] don’t treat me like some situation that needs to be handled.” 

From “Evermore (Deluxe Version),” I have to go with the song “Closure.” This song resonates so much more with me now that I’m older. When I was young, I had this tendency to try and make everyone else around me happy, usually at the expense of my own well-being. It quickly became exhausting and, ultimately, extremely damaging to my self worth. Over time, I have learned that my first and most important responsibility is myself: if someone is not benefitting my life with their presence, they don’t need to be a part of it. I don’t need to maintain peace unnecessarily, or make others feel comfortable when they have hurt me. Even if someone who has treated me poorly in the past reaches out with an apology, I am not obligated to take it, or even listen. My priority is to myself and my happiness: a concept I am learning to accept more in my 20’s. 

“No one likes a mad woman / you made her like that / and you’ll poke that bear ‘til her claws come out / and you’ll find something to wrap your noose around.”

Actions have consequences. Honestly, that’s all there is to it. “Mad Woman” off of “Folklore (Deluxe Version)is a song that resonates so deeply with me, especially as a young woman learning to navigate today’s society. Our society always tells women to take everything thrown at them without complaint. We have to live up to this impossible standard, yet simultaneously maintain grace while doing it all. Even when we’re faced with such blatant prejudice, somehow it always seems to be our fault for “overreacting” when we fight back or lash out. But there comes a time when enough is enough: it is exhausting trying to live up to this unrealistic notion of “perfect” all of the time. We are human, it only makes sense that we will lash out when someone pushes us too hard. Like I said, actions have consequences. 

“I forgot that you existed / and I thought it would kill me, but it didn’t / and it was so nice / so peaceful and quiet / […] it isn’t love, it isn’t hate / it’s just indifference.”

Like I said before, I’m a woman who feels her emotions extremely fiercely; that can sometimes make life kind of difficult to handle at times. So, to me, there is a special type of beauty in feeling indifference. It means that you have finally started on the process of moving on. When I was younger, I found that the “no contact” route was always difficult for me to follow through on. It pained me horribly to cut people off when they hurt me because I was such an intense people pleaser. I just wanted everyone around me to be happy, and I had such a fervent desire to be accepted. As a person of color growing up in a predominantly white area, I always felt somewhat out of place. I desperately wanted to fit in (like most kids do), and I subconsciously felt that I needed to overcompensate for my differences by being the “perfect” person who never got upset or angry with others. I begged for acceptance, even from people who had treated me with such cruelty, which was ultimately not helpful to my progression in life. As I grow older, I am learning that there is beauty in my differences, and I deserve to be treated with the same respect that I give to others. I am learning to put myself and my well-being first. It can still be a struggle at times, but I am learning as I go. A key aspect of putting myself first means that it is okay to cut off contact with people who have hurt me. It might be difficult at the moment, but over time, I begin to forget about their negative impact on my life: I stop dwelling on the pain. That’s why “I Forgot That You Existed” off of “Lover resonates so deeply with me. I have learned to expel the negative energy, which proves to be much more peaceful at the end of the day. 

“If a man talks shit, then I owe him nothing / I don’t regret it one bit, ‘cause he had it coming / they say I did something bad / then why’s it feel so good?”

Keeping with the theme of learning to prioritize myself as I grow older, I have to go with “I Did Something Bad” off of “Reputation.” Look, if I’m going to be perceived as a shrew, I might as well be one. It can be so cathartic to lash out at the people who deserve it every now and then. Is the most healthy, evolved response to fight fire with fire? Okay no, probably not. That being said, it can sometimes be the most satisfying one. There’s something almost euphoric about being able to speak my mind without censoring myself and worrying about someone else’s feelings: something I am learning to be more comfortable with doing as I grow older. I don’t owe anything to people who aren’t beneficial to my life, and sometimes being a shrew can be the best outlet.

“And his voice is a familiar sound / nothing lasts forever / but this is getting good now.”

Okay, honestly, “Wildest Dreams” off of “1989 is kind of my cheat for this list: to be completely transparent, this song has meant something special to me ever since I was younger. That being said, the way that I resonate with this song has changed over time. When I was younger, I listened to this song to escape into my imagination; I escaped into a world where I was a princess in a meadow, frolicking without a care in the world. But now, as I grow older and experience love and heartbreak for the first time, the meaning of this song has evolved for me. As a result, the way I listen to and process this song has also changed for me. In our generation, especially at this stage in my life, the general collective view on love seems kind of like a rejection of it. Most people my age that I meet aren’t interested in developing a soul-tie with someone else. Memories can be fleeting, people and love can be volatile, and I have found that you have to adapt to having short-lived moments in your 20’s. But that doesn’t exactly mean that I have to shut my emotions off entirely when interacting with others: I truly don’t think I ever can. This song reminds me that there is beauty in feeling something so strongly for another person at a specific moment, even if it’s just a fleeting moment at that. I mean, might as well enjoy the ride. 

“I’m alone, on my own / and that’s all I know / I’ll be strong, I’ll be wrong / oh, but life goes on / oh, I’m just a girl / trying to find a place in this world.”

Last, but certainly not least, I have to go with “A Place in this World.” Navigating life in your 20’s can be confusing and taxing, but it’s a necessary part of growing up. For many of us, it’s our first time truly trying to make sense of everything on our own, without any support. In your 20’s, you’re trying to figure out what steps you want to take for your future and where you will be the happiest in your life. You’re really trying to make sense of what your “place in this world” is. It can be daunting, but it’s part of growing up. 

Experiencing your 20’s kind of feels like a fever dream. It’s a weird balance between becoming an adult and dealing with the unpredictability and volatility of life. Taylor Swift’s music has always been good, but lately, it has been resonating with me on a deeper level that I have never truly experienced before. As she releases more music as I grow older, I realize how formative to my development her music has been. She is truly one of the most influential musicians of our generation.

Aarushi Singh

CU Boulder '25

Aarushi is currently a third year at CU Boulder majoring in Neuroscience and Psychology, with a Pre-Med focus. After Undergrad, she hopes to work as an EMT during her gap year before medical school. When she's not studying or working, you can find her reading one of her various romance books, looking for new music to listen to, and binge-watching 'New Girl' for the millionth time.