Moral and ethical dilemmas surround Flynn's adulterous affair; the college recruitment of Winslow's basketball star; and the plight of a pregnant teen.

Hanson, looking for a way to increase his chances in adopting his niece, makes a sudden proposal to Claire (Missy Yager). Meanwhile, Guber challenges a student (rap star GQ guest stars) who wants to use rap music to show why Shakespeare ""sucks""; and Marilyn doesn't trust a record producer (hip-hop star/actor Method Man guest stars) who's pushing to sign Aisha to a recording deal. Also of note for this episode, the band Lifehouse (""Hanging by a Moment"") will perform at Doyle's Bar.

Guber discovers the high-school drum line's freshman hazing involves physical abuse; a student-produced TV documentary about Ronnie worries her; a father is sentenced to being handcuffed to his son for a week.