Jeffie Was Here (2010)

It's been a rough couple of years for Alan Mangold, a tightly-wound professor in his 30's who dreams of a better life beyond his shoebox apartment... if only he could complete his opus, "Orphan Bastard." When his Nana dies, Alan and his better-half Amanda must post an internet ad at the university to find a student who will share the costs of the emergency cross-country trip. Enter Jeffie: an inflammatory individual who fancies himself a scholar, a poet, and the embodiment of enlightened living. At first, the couple's travel companion seems to have responded randomly to their ad, but as the trip progresses, it becomes clear that Jeffie's presence relates to a web of tightly-held secrets between Alan and Amanda. Amidst infidelity, blackmail, run-ins with the law, and a painfully bad demo tape, the ride with Jeffie is unpredictable at every turn and by journey's end no one is left unchanged.