Christianity and popular culture are two major, yet opposing lifestyles for every Christian adolescent. The need to please God and look cool is a daily struggle most of the youth face, and the fear of being shunned, mocked, or isolated entirely haunts them; hence the choice for the latter. The author addresses various areas of pop culture including music, fashion, and social media and tries to juxtapose with God`s Word in the manual for Christians – The Bible, and outlines ways to deal with the “entanglement”.