Song Meaning

B.o.B's "Choose Wise" dissects the aftermath of a relationship weighed down by unresolved issues, exploring themes of superficiality versus genuine connection. The song's core revolves around the singer's reflection on a past love, contrasting his initial intense feelings ("I used to miss you, used to kiss you, used to hold you") with a present-day detachment. This shift suggests a journey of emotional processing, where the initial longing has faded into a more detached observation. He's moved on, but the specter of what went wrong still lingers, prompting a cautionary message directed not at himself, but seemingly at his former lover. The repeated questions directed at the ex-lover – "Tell me this you new boo? And does he ever get you high? And tell me when you feel blue, and does he ever paint your skies?" – aren't necessarily born of lingering jealousy. Instead, they highlight a concern about her well-being and the quality of her current relationship. The line "But don't tell me too much" suggests a boundary, a reluctance to be drawn back into her emotional world. It's as if he's saying, 'I care, but I can't afford to care too deeply.' The chorus, with its probing question "Is you beauty deep, or just seen by the sun?", cuts to the heart of the matter. B.o.B questions the authenticity of her allure, hinting that her appeal might be skin-deep, lacking the substance needed for a lasting connection. The phrase "Choose, choose wise, we may not get this chance next time" serves as the song's central warning. It transcends the context of romantic relationships and becomes a broader commentary on the importance of making sound decisions in life. The "treacherous streets" mentioned in the lyrics further reinforce this idea, suggesting that life is fraught with peril and that careful choices are essential for navigating its complexities. The outro, with its declaration of indifference ("I don't even miss you, don't need to kiss you, Don't need to hold you"), is somewhat undermined by the admission that he's "just checking on you." This final line reveals a lingering concern, a subtle contradiction that adds depth to the song's exploration of post-relationship emotions.