In ‘I Look in People’s Windows,’ Taylor Swift explores the aftermath of a lost connection, reminiscing about fleeting moments and yearning for what could have been. She reflects on the subtle gestures and encounters, singing, ‘I had died the tiniest death, I spied the catch in your breath.’ Despite the distance, she finds herself drawn to the hope of encountering the person again, pondering, ‘Does it feel alright to not know me? I’m addicted to the “if only”.’ Swift portrays the bittersweetness of observing others' lives, imagining scenarios where they might cross paths, lamenting, ‘So I look in people’s windows, like I’m some deranged weirdo.’ She longs for a chance encounter, imagining the possibility of their eyes meeting once more, singing, ‘What if your eyes looked up and met mine, one more time.’ Through poignant lyrics and wistful melodies, Swift captures the ache of longing for lost connections and the quiet desperation of seeking closure.

The title and the premise of the song could be referring to Emily Dickinson’s ‘I had been hungry, all the Years’, in which the persona talks about a life of being outside a house and looking in through a window, which symbolises a longing for connection. Swift herself was recently revealed to be distantly related to Dickinson, and has previously mentioned that “If my lyrics sound like a letter written by Emily Dickinson’s great-grandmother while sewing a lace curtain, that’s me writing in the quill genre”.