This quote on page 330 of Gary D. Schmidt's novel "Okay For Now" represents a pivotal point in the life of the protagonist, Doug. In the novel, Doug has just moved to a new town with his abusive father and loser brother, and he is feeling lost. For once, he has a place in life and is experiencing real friendship with a local girl, Lil Spicer. She has procured him a job at the deli her parents own and he has begun to forge relationships with all the locals in Marysville that make him feel connected to the town in a way that he never expected. Lil, it seems, has had an extremely positive influence on his life, and is single-handedly responsible for everything good that is happening to him.
At this point in the book, however, she has experienced a tragic illness and is in the hospital fighting for her life. Doug visits her, but her illness has affected his newfound happiness in unexpected ways that make him feel like a "chump." The use of the word "chump" is significant because it refers to someone who feels stupid or foolish; in this case, Doug feels like a chump for believing that everything could end well for him. He feels foolish for allowing himself to be lead into a false sense of security and for letting himself experience happiness for the first time in a long time.
First, he feels like a chump because even when Mr. Spicer has to fire him to pay Lil's hospital bills, he offers to stay on for free. Then, when the neighbors ask about her, he almost bursts into tears, which makes him feel foolish. When he
returns to the deli and sees Mrs. Spicer crying, he cries and feels a little less foolish because they are "chumps together," meaning that they are crying and acting foolish together.