On the day of parent-teacher conferences, Dicey comes home to find that Gram has grounded the younger children to their rooms, because when Gram came home from the conferences she found them in the attic without her permission. Dicey retires to the barn, and soon after, James appears, explaining that they had been curious to find relics of their Momma's childhood, especially a photo album. Dicey tells James that Gram was right to ground them, but James expresses his desire to find an album and learn more about their family history. That night at supper, when the children ask Gram about parent-teacher conferences, Gram announces that she and Dicey will take a shopping trip the coming Saturday and discuss the conferences before they talk about them as a whole family.
That Saturday, Dicey and Gram take the bus to a mall in nearby Salisbury. They buy wool for sweaters, jeans, and shirts. After each purchase, Gram presents Dicey with one of her siblings' problems: Maybeth is failing, despite being well behaved and working hard. Sammy is behaving perfectly, but, Gram feels sure, is bottling up his personality and masquerading as the student the teacher wants him to be at school. James is dumbing down his work—he turned in a different, less excellent, report than the one he shared with Dicey and Gram. Gram then marches Dicey into a restaurant, and, although Dicey tries to order one of the cheapest items, Gram insists she order a club sandwich as a treat. Gram then asks for Dicey's ideas about her siblings, explaining that her vacation from worrying about her siblings is over.
Together, Gram and Dicey brainstorm sources of the problems the younger children are facing. James, Dicey explains, has always wanted to be liked and thus is probably dumbing down his work to better blend in with his classmates. Dicey, after imagining Sammy donning a heavy mask before school every day, explains to Gram that as a child she had fought other children because of what they said about Momma, and that the other children learned to leave her alone. Together, the two discard the idea of having Maybeth work with a tutor from school, who will merely instruct Maybeth in the same ineffective style in which her teacher instructs, and instead decide to ask James for ideas. At the end of their conversation, Gram commends Dicey for her devotion to her siblings, and again emphasizes how important it is to hold on to them. Dicey brims with questions about Gram's past, but reins them in.
Next, Gram herds Dicey into a department store and announces to a saleslady the Dicey needs a bra. Dicey is shocked and humiliated and stands stonily as the saleswoman measures her. She feels disgusted at how expensive they are, but takes grim satisfaction in the fact that Gram will have to pay dearly for making her so uncomfortable. Afterward, Gram has Dicey try on a denim jumper and a brown velvet dress, both of which suit Dicey well. Dicey's anger begins to wane as she looks at herself in the mirror and almost does not recognize the elegant, womanly figure reflected back to her. The pair then finalizes their plans: they cannot tell James that they know what he did, and they must let Sammy know indirectly that they want him to be himself in school. On the way home, Gram turns to Dicey matter-of-factly, announcing that Dicey needs attention as well. Dicey, intuiting where Gram is headed, cuts her off, asserting that she already knows about sex and menstruation, and will ask Gram if she has questions. Gram seems satisfied, but observes that Dicey does not seem happy about the prospect of growing up.
Gram and Dicey's shopping trip establishes a parallel between caring for people physically and caring for them emotionally. The trip allows them a chance to buy needed winter clothes and to put their heads together about the problems and challenges that surfaced during the parent-teacher conferences. As they shop, Gram alternates between handing Dicey a bag of clothes and handing Dicey a piece of troubling news about each of her siblings. By the end of the morning, Dicey is weighed down both by shopping bags and by the problems her siblings are facing. During their trip to Crisfield, Dicey devoted her entire existence to securing the physical safety and security of her siblings, and during their first month there, she found herself content as long as nothing dramatic or threatening was taking place in her siblings' lives. At lunch with Gram, however, Gram issues a wake up call, essentially telling Dicey that Dicey must hold on to her siblings not by merely providing for their physical well-being, but by being involved in their emotional lives and their problems as well.
Dicey's Song is a young adult problem novel, a genre characterized by realistic settings and situations and non-romanticized characters. Problem novels often focus on family relationships, friends, body image, and sex, and depict children compensating for the weaknesses of adults around them. Dicey's Song follows this paradigm, but with slight variations. Although Momma's problems and shortcomings have required the children to grow up quickly and learn to fend for themselves, Gram takes the Tillerman children in. She does not, however, rescue them from hostile surroundings. Gram is at best an ally for the children. She works beside them, trying to help them learn how to deal with their own problems. Gram also turns to Dicey for consultation, instead of merely assuming the role of parent entirely for herself. She enlists Dicey's help directly and sees such assistance as being Dicey's responsibility. Gram's demeanor toward the children gives an example of an adult working side-by-side with a young adult to solve problems in their lives. Neither is perfect or all knowing, and both grow from the alliance.
Dicey's hostile reaction to Gram's decision to purchase bras for her illustrates Dicey's inner conflict about growing up and about conventional gender roles. Throughout Dicey's Song and its prequel, Homecoming , Dicey displays not so much rebellion against conventional conceptions of gender roles, but impatience with the impracticality of gendered behavior. For example, Dicey parades around without a shirt when she is working on the boat because it is comfortable, trying to ignore the fact that her body is changing. She despises home economics class not explicitly because the class makes the assumption that girls need to know domestic skills and not mechanical drawing, but because she has no interest in or need for skills such as sewing. Dicey defies gender conventions not out of a sense of ideology, but out of a sense of pragmatism and realism. At the same time, her resistance to the constrictions of her gender is also a resistance to the very fact of growing up. She does not resist out of a sense of dread of assuming an adult female role, but merely out of a fear of change and adulthood. As far as Dicey is concerned, gender is merely another characteristic of the adult world and of society in general, and Dicey has become accustomed to avoiding adults and society as much as possible.