The ending is not like a short story
I thought the ending matched the conversation the two characters (Dell and Kimberly) have about short stories having endings and how in real life there is no conclusion because you don't know what's really going to happen. I think the story within this film left off on an ambiguous note because nobody knows whats going to happen, even Dell and Stephanie.
Dell spends a lot of the film analyzing the world and even though he's brash and tactless, he's usually right because he does have a keen eye. But over-analyzing and pessimism and the need to be right all the time is ultimately his downfall. He pushes Stephanie away.
It's funny because she mentions that being with him was good for her. It helped her to reexamine her life choices. And even though Dell doesn't know it yet, Stephanie was probably good for him in the same way.