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.

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.

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.