We meet the staff of 101.7 THE JAMZ, the top-rated radio station in Chicago. When Kasey, the host of the #1 rated morning show in Chicago, announces his impending retirement, Jay-Jay & Fitzy find themselves scrambling to get out of their overnight graveyard shift and into Kasey's coveted morning show timeslot. After storming into Program Director Danielle "Dan" Hansen's office and accidentally quitting their jobs, Jay-Jay and Fitzy beg their coworkers (Stanton, Chrissy, Wyatt, and Intern) for help proving to Dan that they deserve the morning show instead of midday host Geena. While they can't get Dan to commit to them as a replacement, they do get their jobs back and Dan's word that they will eventually be considered. Meanwhile Fitzy, trying to impress his work crush Chrissy, spills coffee all over her expensive shoes. To make up for his blunder, Fitzy purchases new shoes for Chrissy as a gift, but learns that she thinks of him only as a friend.
After watching Jay-Jay play a show at a third-shift fireman bar, Fitzy takes it upon himself to book Jay-Jay a gig at a "real venue" in an effort to see Chrissy outside of work. When he learns that she will be at a bachelorette party the night of the concert, Fitzy rebooks Jay-Jay's show at the bar next door to the bachelorette party location. Jay-Jay and Geena battle for Kasey's attention, but find that focusing all their attention on impressing Kasey caused their workplace performance to slip. Dan and Chrissy, in an effort to learn what the younger demographic is into, spy on Intern and find themselves completely confused by everything he does. After confronting him, they learn the entire staff has been using him as a personal errand boy.
To make up for accidentally hanging up on Liam Neeson during a sponsored interview, Jay-Jay and Fitzy attend an apology lunch with the client and Account Executive Stanton on a Saturday. When they learn Kasey and other members of the office will be helping Chrissy move out of her apartment at the same time, they both send Jay-Jay's fiancé Julie to act as their mole, hoping to get plenty of face-time-by-proxy with Kasey and Chrissy. When Kasey sends movers instead of going himself, the move turns into a drunken day at the Fire Hose Bar. Geena learns of Julie's mole status and uses it to mess with Fitzy. During all of this, Wyatt interviews Patrick Shane of the Chicago Blackhawks during his Saturday Public Affairs Show, but neglects to tell Jay-Jay. When Jay-Jay learns that his favorite athlete is being interviewed, he storms out of the client lunch and rushes to the station, hoping to catch a glimpse of Shane.
When Jay-Jay finds cryptic music videos posted online by his songwriter ex-girlfriend, he becomes obsessed with trying to figure out which songs are about him. He also connects with Kasey over their romantic pasts and is invited to his office for bonding and scotch. Meanwhile, Fitzy inadvertently leads Chrissy to believe that his mother is dead and is torn between enjoying her affection or telling the truth. Dan invites possible "Jamzing in the Park" headliner Jeremy Mraz to the station to close the deal on his performance. Throughout his stay, Mraz both offends and impresses various members of the staff. Fitzy explodes when he watches Mraz hit on Chrissy, nearly blowing Dan's opportunity to sign Mraz as a headliner.