Emily, Olivia, and the rest of the theater company prepare for the musical. In the meantime, Josh and Adam attempt to help make amends between Erin and Emily.
Shenanigans ensue as Adam is pressured into selling cigarettes to two underage delinquents. While this is happening, Emily and Erin compete for the lead role in Chicago.
In the midst of Valentine's Day, drama begins between Emily and Erin. Meanwhile, Adam and Samantha go on a date where the accidentally go to the same restaurant as Mason and Sophie.