Before performing her song “Fearless” for the first time, while it was still technically unreleased, Taylor Swift introduced it as a story about “the best first date [she hadn’t had] yet.” The song went on to become the title track of her sophomore album and the introduction to her series of rerecordings.

With the familiar drum kick and intro melody to the album Fearless (Taylor’s Version), the instrumentals conjure up images of sparkly guitars, sequined dresses, wild curly hair, girls spinning in the rain, and hearts made with hands 🫶. Swift has built her career, and most recently her Eras Tour, by marketing certain motifs through the aesthetics of each album, and Fearless was her first experimentation with this ultimately incredibly effective concept.

Even upon listening to this record for the first time, it radiates nostalgia and unbridled optimism. Swift arguably found success as a young songwriter with little experience because despite leaning towards autobiography, she’s always had the capacity to daydream; Fearless is an album centered around those daydreams. Her song “Today Was a Fairytale” embodies this starry-eyed idealism, depicting yet another imaginary perfect day, which is seen again in her first real hit, “Love Story.” “Hey Stephen” serves as a love letter to a boy who “look[s] like an angel,” in which Swift reminds him that “all those other girls, well, they’re beautiful / But would they write a song for [him]?” With Fearless, Swift projects every facet of her idealized personality into her music; she’s cheeky, witty, trusting, empowered, and willingly donning her rose-colored glasses.

Of course, the record isn’t all unbridled joy and fantasy – ballads like “Breathe,” “White Horse,” and “You’re Not Sorry,” are among the album’s most harrowing songs. Once again embodying the relatable teenage girl, Swift discusses heartbreak from friends and relationships; however, the distinguishable quality in almost all of these tracks is that despite her dejection, the takeaway of the song still highlights some form of self-efficacy and independence. In “White Horse,” particularly, Swift expresses her confidence that she will “find someone someday who might actually treat [her] well,” and similarly in “Fifteen” she emphasizes the importance of self-discovery despite the setbacks that might occur due to heartbreak.  Swift demonstrates her lyricism more subtly on this album, stringing together complex verses, like in the outro of “The Other Side of the Door” and between the nuances in “The Way I Loved You.”  The conclusion of the original album and the heart of the rerecorded Fearless (Taylor’s Version), the song “Change” reminds listeners that they can overcome any setback and further bolsters her messages of resilience and faith.

As for me, Fearless is usually my go-to happy album for sunny days in May. Classics like “You Belong with Me” never fail to lift my mood, and “Mr. Perfectly Fine” often seems like the perfect choice to scream in the car with friends. With Fearless, Swift paired her own self-discovery with her burgeoning imagination, creating a timeless record with the capacity to captivate listeners in both 2009 and 2021.