In the midst of a career crisis and much to Annie's dismay, Eric takes a job as a talk DJ at a college radio station, but things become serious fast when Eric and his producer (guest star Usher) find themselves counseling a male student who calls in threatening suicide during his first shift. Meanwhile, Lucy refuses to spend time with Roxanne which puts Kevin in an impossible situation. Later on, Roxanne asks her boss to assign her a new partner as tensions simmer between her and Lucy. Ben is almost arrested when he accompanies Simon and Cecilia to an underage club. Lastly, and Ruthie tries to figure out a way to breakup with her boyfriend (guest star Oliver Adams) without making him cry.