Dicey understood, just then, and wished she didn't, just what the Tillermans had done to Gram by coming to live with them. Because she did love them, and that meant not only the good parts, but also the worry and fear. Until the children came along, nothing could hurt Gram. And now but Gram must have known that, she'd had children of her own, she much have now that when she said they could live with her. Dicey wished she didn't understand. She wished she could still be like Sammy, concerned only about whether or not he'd have as much steak as he wanted, already forgetting the worry since everything was all right again.
Dicey realizes how deep an impact the Tillerman children have on Gram's life at the end of Chapter 3. First, Gram has just received her first welfare check and angrily prepared a celebratory dinner. Second, Gram sat waiting and worrying for more than an hour, as Mr. Lingerle, bringing Maybeth home, got a flat tire and could not call to tell Gram, as she has no phone. Third, upon Mr. Lingerle and Maybeth's arrival, Gram resolves to reinstall a phone, after being without one for so many years. Dicey notices the smaller ways in which the children are changing Gram's life by requiring her to be in greater contact and greater independence with the outside world, in the form of the welfare checks and the telephone. For years prior to this, Gram enjoyed her stoic, proud, and completely isolated life, but the Tillerman children are requiring her to interact with the outside world and accept charity. More importantly, the Tillerman children themselves embody a deep connection to the outside. Gram cares about the children and thus becomes four times as vulnerable to pain and loss now that they are in her life. Gram had been shut off and protected, willing to live with the results of all her decisions, and now she must learn to live with the results of everything that happens to all of them.
"But I'll tell you something else, too. Something I've learned, the hard way. I guess"—Gram laughed a little—"I'm the kind of person who has to learn things the hard way. You've got to hold on. Hold on to people. They can get away from you. It's not always going to be fun, but if you don't—hold on—then you lose them."
Gram speaks these words to Dicey in Chapter 4, while the pair eats lunch at a restaurant in the mall in Salisbury. By explaining that she herself has learned the importance of holding on the hard way, Gram acknowledges that she herself failed to hold on, and makes oblique reference to the way in which she allowed her children to be driven away from her by her husband's bitterness. Gram's admission comes in the middle of a lunch during which the two are discussing the problems each of the siblings is facing, trying to explain to Dicey that being involved in a person's problems and working to help them is one way of holding on to them. Dicey has been drifting away from her siblings, feeling that her responsibility for them, now that they are physically safe, has ended. Here Gram argues to Dicey that she must also take responsibility for her siblings' emotional well-being.
I got to thinking—when it was too late—you have to reach out to people. To your family, too. You can't just let them sit there, you should put your hand out. If they slap it back, well you reach out again if you care enough. If you don't care enough, you forget about them, if you can.
Gram tries to explain reaching out to Dicey in Chapter 7, just after Dicey has shown Gram her essay and told how Mina defended the essay from Mr. Chappelle's accusations. Again, Gram embeds this in memories of her own past, reflecting first upon the way in which she failed to reach out to her husband, despite the fact that she recognized his unhappiness, and to her children, who drifted away from both of them. Reaching out consists of offering part of yourself, your history, or your emotions to another, as, Gram argues, Dicey did with her essay about Momma. Ironically, Gram's realizations about holding on and reaching out do not come too late. Instead, they come in time for her to reach out and hold on to her grandchildren, and in time for her to teach them their importance.
"You have to let go," Gram said harshly, in Dicey's ear. But she didn't loosen her arms. "You have to and I have to." Dicey understood. It was Momma they had to let go of. "I don't want to," she answered softly. Gram pulled her head back so she looked into Dicey's face. "Neither do I," she said. "But I will, and so will you. Because if you don't—let go—it can make you crazy."
Gram and Dicey exchange these words in Chapter 11, just after Dicey has seen that Momma is dead. At this point in the narrative, the two are hugging each other—literally holding on to each other—for the first time. Here Gram offers the counterpoint to her first two pieces of advice, to hold on and to reach out, because there are times when one can no longer reach out and hold on, but must let go. This piece of advice gives Dicey the chance to forgive herself, to let go of her failures, to let go of her past understanding of herself, to let go of the people whom she could not help. Gram gives Dicey this maxim shortly before she herself fully lets go of her anger at herself for failing her children, and shares the family albums and the family history with her grandchildren.
What I mean, girl, is you keep trying. One thing after another. Sometimes just one, sometimes all three, but you have to keep trying. I don't have to tell you that, do I?
Gram answers Dicey's question about how to know when to reach out, when to hold on, and when to let go when they are on the train from Boston to Wilmington in Chapter 11. Gram's answer is confused and indeterminate, as she tries to explain to Dicey that there is no clear-cut answer to how best to relate to others and build a life rich in connections and love. Dicey is unhappy with the answer, but she sense that Gram speaks the truth that relating to others will never be easy or predictable. As far as Gram is concerned, human relationships turn out the way they want to, but the only true failure of another person is giving up on them.