Childhood friends Sidney and Dre, who originally bonded over their love of hip-hop, face an evolving relationship as adults. Sidney has just been appointed the editor-in-chief of the hip hop magazine XXL, and Dre is an A&R for Millennium Records. While Sidney's career is flourishing, Dre is increasingly frustrated with his label's preference for marketable artists over true talent.
Dre meets and falls in love with Reese, a successful entertainment attorney, and soon becomes engaged to her. The night before Dre's wedding, he and Sidney kiss and almost have sex, but they stop themselves. At the wedding, Sidney's cousin, Francine, deduces the romantic tension between Sidney and Dre and encourages her to object during the ceremony. She does not and Dre settles into married life with Reese. Sidney, meanwhile, begins dating professional athlete Kelby Dawson.
Dre sees Cavi, a rapper who works as a taxi driver during the day, perform and is impressed with his talent, but Cavi is not interested in signing with Dre's label because he does not like the music that they produce. Dre's boss meanwhile pushes him to manage an untalented but commercially viable rap group, forcing him to choose between his income and his love of hip hop. He decides to quit and form his own label, focusing on bringing back the real hip hop that his generation fell in love with, and manages to sign Cavi.
Reese is unsupportive of Dre's new business venture, concerned it will fail and they will be forced to live in reduced circumstances. Meanwhile, Sidney draws closer to Dre due to their partnership in the label, and Reese develops jealousy over Dre and Sidney's friendship, while Cavi falls for Francine but struggles to muster the courage to ask her out.
Sidney also grows closer to Kelby, who proposes to her. Dre tells her that he is against her marrying Kelby because he thinks that he is inauthentic. Sidney does not agree, but begins to have doubts when she discovers that Kelby does not read her articles.
When Dre discovers Reese has been cheating with a man from the gym, he brings Sid to catch her in the act. This leads to a night of shared passion between Dre and Sid and opens Sid's eyes to the fact she is not prepared to marry Kelby. She calls off the engagement and while searching for Dre sees Reese and Dre in a parting embrace that she misconstrues as more.
While at Hot 97 waiting for Cavi's first single to play on the Angie Martinez show, Dre hears Sid talking about her new book I Used to Love H.I.M. Though based on her love affair with hip-hop, it really is a chronicled timeline of her love affair with Dre. He recognizes this and rushes over to the station to confront his feelings, as well. Meanwhile, in the production booth, Cavi stumbles in trying to ask Francine out again. She recognizes their attraction and asks him out on a date. The film ends with Cavi's song playing in the same park where their love of hip-hop began.
