How Many Times by Cat Stevens is a reflective and soulful song that delves into themes of love, introspection, and the passage of time. Through its poignant lyrics, the song explores questions about past experiences and the emotions tied to them. Cat Stevens asks rhetorical questions, longing for understanding and connection. The song's key moments involve these questions which reveal a yearning for clarity and closure. The recurring lines emphasize the contemplative nature of the song, engaging listeners in a deep, personal journey.