Wisconsinite Bob Murray finds himself in the awkward position of being a bachelor at 34 while all of his peers are settling down and starting families. Wondering if it's the Milwaukee dating scene or his own neuroses that have kept him single, he embarks on an ambitious road trip from Milwaukee to Los Angeles, with eight dates scheduled in eight different cities, to put his theory to the test. What begins as an attempt to utilize the ever-popular medium of online dating as a means of finding true love turns into a journey of self-discovery.