In trying to prove to Diane that hip-hop isn't dead, Dre realizes he may be more of out of touch with current trends and his clients than he thought. Meanwhile, Jack thinks that he has somehow become Bow's best friend now that Junior is too busy with his new girlfriend.

Bow and Dre let their competitive streaks out during their family game night and things escalate when they place a bet. Meanwhile, Junior and Olivia are at a turning point in their relationship when one person says "I love you".