Josh and Michael, two college friends, take an emotional and eventful road trip from Los Angeles to Chicago to attend their 10-year college reunion. Nearly 30, both are living in complacency—neither fulfilled by their daily lives. They want to grow up but it doesn’t look like that will happen any time soon. They head eastward across the United States and ultimately visit nine cities, traveling from Los Angeles to Las Vegas, to the Grand Canyon, to Albuquerque to Amarillo to St. Louis, and finally landing on the shores of Lake Michigan in Chicago. This journey across the country elicits reminiscences, confessions, and contradictions of each other’s versions of the past.