"Ruin the Friendship" is a song by Taylor Swift from her 2025 album "The Life of a Showgirl." The song is about a poignant regret from her high school days, where she had feelings for a male friend but never acted on them. Later, she learns from her longtime friend Abigail that the boy has passed away. The song reflects on the missed opportunity to turn their friendship into a romantic relationship, with Swift lamenting "Should've kissed you anyway." The message advises taking risks in love rather than living with regret, capturing the emotional weight of lost chances and the complexity of friendships that could have been something more.
