The song looks at the topic of romance from several points of view, and in doing so, touches on other subjects such as illegal drugs, the city of Los Angeles, the perceived glamour of gang culture, and the lavish, hedonistic lifestyle led by many rappers and musicians.
The chorus, sung by Justin Timberlake, is about the moment when a man thinks a woman to whom he is sexually attracted may also be attracted to him. The man second-guesses what he thinks he has seen, expressing a wish that love (personified as Cupid in classical fashion) should not play around with his emotions. Meanwhile, another male observer (voiced by ) opines that the Timberlake character is out of his element and should not bother attempting to further relations between himself and the object of his affection, since he lacks the necessary gangster credentials.