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The Meaning Behind The Song: Riddle by *NSYNC

The Meaning Behind The Song: Riddle by *NSYNC


I remember stumbling upon this song at a friend’s house many years ago. As soon as I heard the mesmerizing melody and the soulful vocals of *NSYNC, I was captivated. “Riddle” is a track from their self-titled debut album released in 1997, and it still holds a special place in my heart. In this article, I want to delve into the meaning behind this song and share my interpretation.

The Search for Answers

“What’s the riddle of it all? What’s the riddle on her mind? It’s impossible to find.” These lyrics from the chorus immediately provoke curiosity and intrigue. *NSYNC’s lead vocalist, Justin Timberlake, sings about the quest for answers, the desire to understand the mystery of a woman’s thoughts and emotions.

The Enigma of Love

The verse continues the theme of seeking answers, with Justin singing, “I’m, I’m out to find the solving key, To this woman’s mystery.” It portrays the universal quest to comprehend the enigma of love and relationships. We often find ourselves caught up in deciphering the thoughts and feelings of our loved ones, hoping to gain insight into their inner world.

The Complexity of Understanding

The pre-chorus asks, “What is going on, what is going on in her life? What is showing up, what is showing up in her smile?” These rhetorical questions reflect the complexity of truly understanding someone. *NSYNC acknowledges that there might not always be a clear answer. People are multi-dimensional, and their lives and smiles can conceal a myriad of emotions and experiences.

The Elusiveness of Connection

The bridge reveals a sense of vulnerability, with Justin singing, “I am only scared from wonder, From delirious I’m running, Tell me, where’s this source of magic, This hide-and-seek makes me an addict.” These lyrics convey the conflicting emotions that arise when connecting with another person. Love can be both exhilarating and frightening, as we navigate the depths of another person’s soul.


Through “Riddle,” *NSYNC beautifully captures the universal experiences of searching for understanding in love. We all long to unravel the mysteries of another person’s heart, but sometimes the answers remain elusive. This song reminds us to embrace the beauty of the unknown and to cherish the quest for understanding.


Album title: ’N Sync (1997)


Justin Timberlake, J.C. Chasez, Joey Fatone, Lance Bass & Chris Kirkpatrick

Mixing Engineer

Joe Smith (Engineer)

Mastering Engineer

Leon Zervos

Copyright ©

BMG Entertainment

Phonographic Copyright ℗

Trans Continental Records, Inc.

Release Date

May 26, 1997

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