Corporate lawyer Nina Whitley has given up a lot in her climb to the top. However, when she's passed over for a promotion and her former fiance gets engaged to another woman, Nina has an epic meltdown.

Phil tricks Nina into believing that all of the public defenders voluntarily go to jail to better understand their clients. She learns what lengths she'll go to be a part of the gang.

An old friend asks Nina to set her up with Phil, a female judge takes a liking to Carlos, and Nina goes on an ill-fated date of her own.

Nina faces a difficult choice after reuniting with Trent; Phil examines his own relationships.