Why? is a powerful thirteen-track collection of songs, brimming with standouts like the finger-clicked soul-pop of "Lovesick" ("A fun song about getting in trouble with your girl") and "You Told Me So," which deeply reflects on the stresses of a long distance relationship. Whitesides' songs are, by and large, heartfelt and relatable. Sometimes they're lighthearted, but even when they're upbeat, there's often another level to the lyrics as the listener dives deeper into the music. "Love Slow" was inspired by the struggle of being 18 and in a relationship, and on "Bury Our Love" when he sings, "I was old before I was young" the line rings particularly true, echoing his musical talents and accomplishments.