Generation Um... is a 2012 drama film directed by Mark Mann. The movie follows John (Keanu Reeves), a disenchanted man in his mid-40s who has been working as a driver for an escort agency for several years. Mark (Bojana Novakovic) and Mia (Adelaide Clemens) are two of the escorts that he spends the day with.
The story primarily occurs in a single day as John drives Mark and Mia around Los Angeles. While they collectively get high, get tattoos, and drink, John realizes that he is missing out on life. He is attracted to Mark but feels like he cannot connect with her on any level other than surface-level small talk. Alternately, Mia seems to have a deeper understanding of him, but they still cannot connect.
As they drive around the city engaging in various activities, John struggles with a sense of emptiness and longing. All three of them are searching for meaning and some sort of direction in their lives, but they cannot seem to find it. By the end of the day, John has lost his job, insightlessly crashed his car, but has realized some level of connection with Mark and Mia.
The movie deals with themes of sexual liberation, finding meaning in life, and the search for human connection. The acting performances are strong, particularly Reeves, who portrays John as a deeply troubled, but sympathetic character. The direction by Mann is understated and allows the performances to shine through.