The song "Ruin the Friendship" by Taylor Swift is about a high school friend she had romantic feelings for but never acted on. She later learned this friend had passed away, which brought feelings of regret for not having kissed him when she had the chance. The song reflects on missed opportunities and the pain of losing someone before exploring a deeper relationship. Swift's advice in the song is to risk ruining a friendship rather than living with lifelong regret for not pursuing it. This friend is believed to be inspired by Jeff Lang, a close high school friend of Swift who passed away at a young age.
