An English professor at a small private college finds his shot at tenure threatened by the sudden arrival of a pretty Yale PhD. onto the staff in this collegiate comedy form the producers of Rushmore. Charlie Thurber (Luke Wilson) isn't interested in school politics, and as a result his career is stalling out. But Charlie's a hit with the students, so when his chance for tenure comes up he's confident he'll get a fair evaluation. That confidence is shaken, however, when Elaine Grasso (Gretchen Mol) is hired on to the English staff. A published writer from a prestigious pedigree, Elaine has accomplished the things that Charlie's only dreamt about. Even Charlie's aging father, a celebrated professor, seems disappointed that his son hasn't accomplished more. Enter Jay Hadley (David Koechner); Jay is an anthropology teacher at the college who also happens to be Charlie's best friend. Jay isn't willing to sit idly by while Elaine takes Charlie's job, and is soon channeling all of his energy to sabotaging the well-intending newcomer's career. But despite being envious of Elaine's accomplishments, Charlie just can't bring himself to hate her; on the contrary, his attraction to her is growing by the day. As the time comes to make some decisions that will most certainly affect the course of his career, Charlie realizes that the only path worth walking is the one that you carve out for yourself.