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.

This song could be a deeper “The Outside” from her debut album as she always felt being left out.