The owner of a Rolls Royce dealership from Chicago requests that Buddy make a special cake with the city skyline and the Willis Tower as the focal point to commemorate its grand opening. Buddy gets a request from a same-sex couple in Long Island to celebrate their upcoming wedding. Buddy asks Grace to head up the renovation of Carlo's Bakery.

Talk show host Regis Philbin stops by Carlo's to learn how to decorate cakes from the Boss himself. Meanwhile, a bride requests a wedding cake to celebrate her 50th wedding! Finally, Joey gets a visit from his old fire chief about his future.