A Bluetooth-enabled tape measuring system, a cooperating mobile or desktop application, and a method for using same. A tape measure with retractable tape stores each measurement taken and transmits the measurement to a computing device for automatic recordation and association with the object of the measurement, which can be a user-input floor plan or the like. A software solution at the computing device is capable of planning necessary measurements, receiving transmitted measurements from the tape measure, and automatically associating received measurements with the user-input characteristics. The system may also direct the user to make certain measurements based on a user-stated project.