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.