The authors discuss some of the challenges encountered in educating the millennial generation of civil engineers. This generation, born during the 1990's, may be characterized by their exposure to smart devices and computers connected to the Internet starting from their toddler years. They have developed a natural affinity and curiosity to take advantage of the computers for play and entertainment, reading, studying, and especially communicating. Meanwhile, most millennial students are proving to be less interested or uninterested in classical math and mechanics, group-thinking and group-studying, and in anything that involves non-virtual media. Alongside their special skills of naturally interfacing with software that promises instant digital and virtual rewards, there are justified concerns in educating this generation due to their general lack of interest in a physical, conceptual grasping of the real world. Without an interest in observation and exploration outside the virtual world, this generation also appears to trust what the virtual world presents to them. These challenges add to the difficulties of the civil engineering profession and education that are among the slowest in introducing technology and innovation.