The Basics
You know this song. You know every word of this song. Taylor Swift compares herself to her friend’s girlfriend and sings about how horrible his relationship is vs. how natural their friendship is. Swift doesn’t understand why he would date “a girl like that” instead of Swift.
Literary Devices: Syncrisis
In the pre-chorus. Swift contrasts herself with her friend’s girlfriend in a series of parallel alternating lines:
She wears short skirts / I wear t-shirts
She’s cheer captain / And I’m on the bleachers
She wears high heels / I wear sneakers
Swift uses these snappy comparisons to indicate that she and this other girl are very different. While her friend’s girlfriend is the archetypal popular girl with cool clothes and a posse of cheerleaders, Swift’s character* is but a slovenly nerd who watches rather than participates.
Analysis
Swift’s tour de force You Belong with Me repurposes and perfects themes that she excavated earlier in her oeuvre. According to the Swiftian theory of epistemology (first outlined in Teardrops on my Guitar and Invisible) there is a difference between looking and seeing, between mere sense perception and understanding. Joining the ranks of the ignorati from these two songs, Swift’s friend in You Belong with Me looks, but he does not see: Swift repeatedly wonders why he can’t see (eee eeee) that he belongs with her, proclaims that “What [he’s] looking for has been here the whole time” and builds the chorus around the proposition that if he could “see” her, they would be together. Swift also revisits the theme of what it means to know another person, previously explored in the paradigm-shifting tracks Tied Together with a Smile and I’m Only Me when I’m with You. Swift equates truly knowing another human being with understanding them, and she provides copious evidence that she understands her friend much better than his girlfriend does. Swift understands his sense of humor, his taste in music, and his hopes for the future. As a result, Swift declares “I’m the one who understands you.”
You Belong with Me places a special emphasis on the theme of communication, revisiting this theme from Stay Beautiful. The first significant word in the song is “phone,” highlighting a communication device right off the bat. From there, Swift portrays two women with different communication styles. Her friend’s girlfriend is a direct communicator. Her role as captain of the cheer squad explicitly casts her as someone who not only communicates, but leads communication. She is also portrayed as a direct communicator in her romantic relationship. Swift may criticize her for “going off about something that you said,” but telling your partner how you feel is an important part of a healthy relationship. Since the girlfriend directly shares how she feels, her partner knows that “she’s upset”.
In contrast, he does not know how Taylor Swift feels due to a passive aggressive communication style that relies heavily on thought transference. Swift has many thoughts and feelings that she never vocalizes: “I can’t help thinking this is how it ought to be / Laughing on a park bench thinking to myself / hey isn’t this easy?” In the pre-chorus she is repeatedly “dreaming about the day when you wake up and find / that what you’re looking for has been here the whole time.” Swift imagines a scenario where her dream somehow results in him waking up with a new realization, Inception-style. Swift portrays herself as intuitive, able to hear what is not said: “You say you’re fine, I know you better than that.” Swift seems to hope that her friend is this intuitive as well so that she never has to express her feelings. Swift asks in frustration: “All this time how could you not know, baby?” The answer, it turns out, is simple: because Swift is a bad telepath.
P.S. One time I got very drunk on New Year’s Eve, called my best friend and shouted this song at him over the phone. I call this communication style “meta passive-aggression.” Anyway, we're engaged now.
*Real-life Swift has many short skirts and high heels and plays a cheerleader in the Shake it Off music video.