Throughout her life, Dicey has become accustomed to rejecting the conventional and breaking with traditional roles. She bemoans the predictability and shallowness of her classmates, she feels no concern for how she looks, she indulges the vicissitudes of her moods rather than acting politely. In the past, Dicey devoted her care and concern to her family to the exclusion of even considering the outside world, but in the space of Dicey's Song, she finds a fellowship of disparate individuals all, in some way, outcasts, gathering around her and in her home. First and foremost, Gram, who has long been regarded as an eccentric around town, begins to form strong connections with Dicey. Next, Gram begins to include Mr. Lingerle in their family circle, and the Tillermans must overcome their tendency to prejudge him due to his obesity, a characteristic that has made him an outcast in school. Jeff, Dicey's friend and suitor, is also a fierce loner, waiting for Dicey each day alone by the bike racks, playing his guitar. Even Millie, whom Dicey and Gram both grow to respect and like, remains outside of conventions, plodding through her life, unashamed of her slowness. These people, each of whom flout conventions or have been shut out of conventional life, are the ones who reach out to Dicey, and stand in contrast to people like Miss Eversleigh and Mr. Chappelle, who, as teachers, traffic in external appearances, such as grades, and fail to see past surfaces. Thus, Dicey's Song depicts outsiders as more interesting, warm, and complex than the popular, pretty, and successful of the world.
Dicey's Song centers largely on the attempts of the characters to learn how to reach out to one another. The novel also more subtly explores a corollary: that receiving gifts or other acts of assistance is also part of reaching out to others. At the novel's opening, Gram, who has willfully shut herself away from society and her family for years, despises nothing more than receiving her monthly welfare check, and Dicey perceives this check as one of the larger burdens Gram must bear as a result of the Tillerman children's arrival. Gram resents this check because it demonstrates that she is not independent. Similarly, Dicey rejects the friendly advances of both Mina and Jeff because she fears the interdependence involved in friendships. As the novel progresses, however, both Gram and Dicey learn the skill of accepting the extended hand of friends. Gram accepts Mr. Lingerle's offer of free piano lessons for Maybeth as she accepts the envelope of money she so desperately needs in the last chapter, and she also accepts the beautiful wooden box from the woodworker. Similarly, Dicey learns to accept outstretched hands. For example, she accepts a ride home from Jeff, she accepts Mina's defense of her in Mr. Chappelle's class, and she accepts the wooden figurine from the woodworker as well. Gram and Dicey accept each of these offers with some difficulty, as in some way these offers put them in the giver's debt. At the same time, they both realize that being in someone's debt is the counterpart of reaching out in generosity of spirit to another, and that refusing these offers is tantamount to refusing to reach out.
Near the end of the novel, Dicey begins consciously to struggle with Gram's advice to her to let go, hold on, and reach out. Although she has difficulty understanding how to perform three contradictory operations, Dicey has already been practicing holding on by letting go throughout her entire stay in Crisfield, as she helps each of her siblings confront a major problem: she helps Maybeth by encouraging her in her piano lessons and convincing James to work with her, she helps Sammy by talking to him and indirectly letting him know that she accepts and understands his fighting, and she helps James merely by being aware of his problems. Dicey's attitude toward her siblings reflects Gram's attitude toward them. Both Dicey and Gram respect the children and, though they remain involved in and aware of their lives, expect the children to solve their own problems. Only through this process of letting go of control can Gram and Dicey expect to hold on successfully to the children. At the end of the novel, Dicey and her family practice letting go by holding on. Up to this point in her life, Dicey worked hard to submerge difficult truths about her past, since she could do little to change them. When Momma dies, however, Dicey takes the chance to reflect back on her experiences and her longings, letting go of them by acknowledging and experiencing them. Likewise, the children and Gram begin to let go of their pain over Momma's death by remembering her and delving, at last, into the family's history.
Voigt uses the motif of music to represent both the act of communal reaching out and being together as well as an act of individual reaching out, as the musician unveils some part of his or her personality to the listeners. When Mr. Lingerle first visits the Tillerman house, Dicey is equally awed by his musical proficiency and his obesity. Jeff's guitar playing and singing by the bike racks causes Dicey to stop and listen almost despite herself, and Maybeth's music serves as a constant reminder to Dicey of Maybeth's soundness of mind and heart. At the same time, music serves as an important locus of connection throughout the novel. Dicey and Jeff sing together, prompting further conversation and even an invitation to hear Maybeth sing, Jeff plays for and sings with the restless and belligerent Sammy in Millie's shop, and all of Dicey's friends and family sing happily together on the day after Thanksgiving. Music serves not only as a way to learn about and appreciate another, but a way simply to be with them as a friend.
Clothing serves two major functions in Dicey's Song. First, clothing represents the ways in which Gram physically provides for the Tillerman children, and second, it serves as an index of Dicey's maturation and growing proximity to the adult world. Gram periodically ventures up to the attic, the repository for all the artifacts of her past as a wife and mother, and brings down warm clothes to protect the children from the coming Maryland winter. When this repository fails, Gram and Dicey shop for the children, loading themselves up with wool, jeans, shirts, and underwear even as they bring their ingenuity and insight to bear on the emotional challenges each child is facing. Gram even knits each child a sweater. As Gram is not a particularly warm individual, these clothes, which provide the children with physical warmth, stand in for and represent emotional warmth and care she provides for them by giving them a home and freedom. At the same time, clothes represent change and growing up to Dicey. Gram brusquely tells the girl she is too old to go around without a shirt in the novel's first chapter, she flinches when she sees the shirts Gram has altered for her emphasize her bosom, she reacts angrily when Gram has her buy a bra, and she looks at her increasingly womanly figure with surprise when she tries on the brown dress. To Dicey, clothes, which are part of the surfaces with which she is so unconcerned, remind her of the fact that she is growing up and drawing closer to the adult world.
Both James and Dicey suffer considerably over writing their assigned essays for school. These essays, as Gram points out, are a way of reaching out, as much as music. James and Dicey cannot express themselves and reach out in the form of music to the extent that the gifted Maybeth can, but they can express themselves well through the written word. Each essay incident illustrates an aspect of their personalities. James writes an unconventional essay about the Pilgrims, both unconventional in its excellence and in its subject matter, which consists of the varied and unexpected reasons for the Pilgrims' decisions to come to America. James, as is typical of his personality, decides to censor this unconventionality, and he turns in a less spectacular essay. Dicey composes an essay narrating Momma's story, unexpectedly reaching out to the essay's readers with this sad part of her past. Mina, the unconventional girl in the classroom, reacts well to the essay. However, Mr. Chappelle and Dicey's other classmates misperceive the work as a piece of plagiarism and remain mystified as to the identity of the essay's subject. Dicey's attempt at reaching out, veiled as it is, results largely in her being misperceived and misunderstood.
Dicey's sailboat becomes as much a part of the routine of the book as it becomes a part of her daily routine. She is always thinking about the finished product, or about supplies for the boat, or wondering where she can find time that day to work on the boat. The sailboat symbolizes Dicey's ability to take care of herself as well as symbolizing her dreams of freedom and motion. At the beginning of the book, Dicey devotes perhaps too much time to the boat, to herself, and Sammy frets restively around her until she strikes a better balance between paying attention to him and working on the boat. The boat remains an almost unspoken dream throughout the book and only in the last few chapters does Dicey begin to imagine vividly and in great detail the act of sailing her boat. The act of sailing, in the wooden boat given to her by Gram, symbolizes Dicey's hunger for freedom and change, even while remaining closely intertwined with her family members, symbolized by the wood of the boat.
Dicey crafts an ugly and useless apron for an assignment, which she is forced to don in front of her classmates. Dicey does not put effort into creating this apron because she is resentful of what she perceives as the uselessness of her home economics class. Dicey has followed the specifications of the assignment while not attempting to understand or create anything functional, mimicking what she perceives as Miss Eversleigh's unreasonable and petty concern for trivial, useless skills. Dicey wears her resentment and disrespect for Miss Eversleigh and home economics by wearing the tattered, poorly created apron.
Gram helps Sammy normalize his social situation at school by bringing a bag of old marbles in the attic and playing with the second graders. This action is symbolically appropriate for a number of reasons. First, Gram again turns to the attic, symbol of her past, for ammunition in helping her grandchildren. Second, Gram cleverly demonstrates to the children, who are teasing Sammy for having a crazy grandmother, that she has indeed not lost her marbles, but is good enough to win all of theirs. The marbles symbolize Gram's devilish and unconventional way of dealing with problems.