Just as Pepper's dating life hits a dry spell, in walks Grady Harper, Chicago's incredibly famous, and available, quarterback. Pepper and Grady are enjoying a romantic dinner when Charlie, Grady's biggest fan, unexpectedly crashes the meal, but Charlie soon notices he is receiving all of Grady's attention. Pepper confronts Grady about his sexual orientation and, along with Charlie, encourages the famous football star to make a big public announcement. Meanwhile, Pepper attends Chick's high school reunion, where music superstar Liz Phair performs.

Pepper Dennis is a beautiful and ambitious reporter with her sights set on anchoring Chicago’s top-rated evening news broadcast. Just when Pepper thinks she’s about to land her dream anchor job, her hot new guy, Charlie Babcock, shows up in the newsroom and steals the job out from under her. Complicating Pepper’s daily life is her needy and recently separated sister Kathy, who has moved in with her. Only Pepper’s close friends and co-workers, makeup artist Kimmy and cameraman Chick, seem to feel her pain.

Pepper’s personal anger during a live interview lands her on the couch of the company shrink, who forces her to confront her issues with Charlie. Meanwhile, Kathy’s desire to please people leads Pepper to discover dangerous hazing rituals at a college fraternity, leading one of the pledges to hold everyone in the frat house, including Pepper, hostage at gunpoint.

Pepper is nominated for four local reporting awards, but is disappointed when her parents refuse to attend the ceremony. To make matters worse, Les orders her off an important story to cover the red-carpet beat at the awards show.

Pepper goes to jail after refusing to reveal a source. While behind bars, she uncovers a scandal that has gone undetected for years. Meanwhile, Kathy enrolls in college to further her career and Charlie has a surprising offer for Pepper.

Pepper's fluff piece about a high-society wedding she is attending takes a serious turn when the bride vanishes, but Pepper has a bigger problem to deal with: her mother is also on the guest list and tries to pair her up with any eligible man she can find at the event.

Pepper investigates a dating service after Kimmy signs up to find the perfect man. Elsewhere, Charlie's too-white teeth are causing a problem for a viewer.

Pepper tries to change her image after testing as too harsh and intense with viewers, but her attempts to soften up go horribly wrong and sink her ratings even lower. Babcock offers to help, but Pepper finds his advice difficult to follow.

Pepper is close to breaking a celebrity-murder-trial story when she is forced to take a vacation by the new station manager. Already upset at losing the story, she is further startled to learn the boss wants to change to a “news-a-tainment” format instead of the hard-hitting journalism she practices.

Pepper gets a lead on a story from her current date, the new mayor, but then realizes he used her report to further his agenda. Meanwhile, Kathy plans to boost morale at the station by holding birthday parties, and she discovers Pepper and Babcock share the same date.

Pepper decides to go undercover to bust a prostitution ring at a club and sees someone unexpected there. Back at the station, she finds herself in a compromising position with Babcock during a sexual-harassment seminar, casuing her to reconsider her feelings for him. Meanwhile, Kathy reconsiders her divorce and agrees to go back to her husband.

In the series finale, Pepper finds herself walking down the aisle after a surprise proposal from Babcock. But the whirlwind wedding isn't as romantic as it seems: Charlie's green card has expired, and a government agent, suspicious of the sudden nuptials, is ready to deport him back to Canada. Pepper and Babcock try to convince him that the marriage is genuine, but real feelings emerge, causing one of them to get cold feet.

After finding dirt on a popular politician just to win a bet with Babcock, Pepper feels guilty when the candidate's numbers drop in the polls. Determined to correct her mistake, she digs even deeper and finds herself getting close to the man. Meanwhile, Kathy schemes to get her job back when the nasty former receptionist returns after maternity leave.