- Tear Jerker: Quite a few, but mainly Liza's death.
- Abigail's reaction to the news that Bullet was killed in combat is quite powerful as well.
- When Abigail tells Dicey about how her children all left her, and how her life had been quite rough and painful for the last several years. Dicey then cries herself to sleep thinking about how hard it's been for her grandmother all these years.
- It's even sadder in the movie, when Abigail breaks down crying over her failures. You can hear the pain in her voice when she tells Dicey "no"; she wants to take them in but she can't bear to set herself up for the risk of failing another set of children.
- The ending is a heartwarming sort of tearjerker in both versions, with Abigail deciding to adopt the kids and telling them to call her "Gram". But the movie adds Dicey's voiceover talking about how their road had ended, followed by "The Water is Wide" playing in the background.
- Near the end of Dicey's Song, Dicey on the train ride home thinks about the previous summer and how she's had to let all of that go, how she's not the same person she was back then.
- The Woobie: All four Tillermans qualify in Homecoming.
- Iron Woobie: Dicey, who tries to stand strong and keep going no matter what life throws at her. It doesn't always work.
- Jerkass Woobie: Abigail in Homecoming; she's stern and harsh towards the children because she's afraid to love them and take them in after what happened with her own kids. She eventually drops the mask, though.
- Poor Liza is perhaps the biggest one of all. She left home to leave an overbearing father only to be with a mariner that doesn't seem to care much for her aside from giving her four children to more or less raise alone. Dicey's paper highlights that Liza would often go to the store but not get anything aside from maybe a can of tuna and often cry to herself. The saddest thing of all is her efforts to keep her head above water fail and after leaving the kids behind, she becomes catatonic and never recovers from it.
YMMV / The Tillerman Family Series