Liberal Arts is about messing up. You make mistakes, you learn from them, and you move on. A lot of things happen in that script that people don't want to. They try to fix their situation, but it doesn't work. They go after their desire, and grab the wrong end of the stick or it turns out it's not what they wanted.
The main character keeps on acting like a clueless chump, until the very end. It's only then that he sorts of start to get it. As you see him evolve throughout the flick, you can't help but cringe at his mistakes.
The movie itself has the incoherence of life, which makes sense. However, the bad part is that it's not done on purpose, including a few incoherence at the beginning. If you get over them, you can probably appreciate the rest of the script. Had I to guess, I'd say all the mistakes of this film lie at the feet of the fact that Josh Radnor, as well as starring is also the writer and the director. By playing that many important roles, each one gets slightly diluted and ends up not being up to par. It takes quite a veteran or a genius to pull that off.
Elizabeth Olsen is as sweet as can be, and plays her role with strong emotions. The other actors pretty much bag theirs just right. The weakest performer is probably Radnor. He gives a good performance, but nothing more.
The whole film is an interesting point of view. I just wish it was better made.