History TearJerker / DearAmerica

** One of the boarders offers [[GiveTheBabyAFather to marry Anetka so she and her three girls a stable income and protection]]. Anetka, having endured a loveless marriage and not wanting to go through it again, declines. This leads to Lidia (who did marry for love) telling her [[YouHaveWaitedLongEnough to think of her three girls]]. No wonder Anetka gets angry with her.

* Throughout the book, Anetka's faith keeps her going, until the end when she finally breaks down and [[CallingTheOldManOut tells God that He is selfish for taking away so many of her loved ones and begs him to say 'yes' to any of her prayers.]]

* Throughout the book, Anetka's faith keeps her going, until the end when she finally breaks down and [[CallingOutTheOldMan tells God that He is selfish for taking away so many of her loved ones and begs him to say 'yes' to any of her prayers.]]

* Grace and her friends (sans Helen) losing the school Dramatic Competition to AlphaBitch Sadie [=McCall=] and her group. To make matters worse, they never stood a chance to begin with: despite their great acting, Grace and her team only have old Victorian dresses for costumes and no scenery. In contrast, Sadie has a beautiful painted set and a glittering dress. It’s a scene that can hit close to home for poor readers.

* The fact that according to the epilogue, [[spoiler: Mary dies of cholera at 17. In the end, she never had the chance to make the life she'd dreamed of having in America.]]

** Even worse, Yolanda’s parents are right: The staff and students ignore or bully Dawnie, and the white parents want her ''dead'' for daring to go to a better school. It’s revealed in the epilogue that Prettyman doesn’t even start enrolling more black children until ''three years'' after Dawnie graduates. It's unfortunate that this cost Yolanda an opportunity and meant Dawnie had to go through it alone instead of having a friend with her, but it's not hard to understand Yolanda's parents just wanting to keep their daughter safe.

** Later, Nancy begins to accept that the woman is her mother, and though she still refuses to leave the plantation for good, she asks another former slave to take her to visit her mother. As the story is told to Patsy, Nancy's mother began crying TearsOfJoy when she realized Nancy is willing to keep her in her life.

* The fact that The Stewarts have lost five sons in infancy, all during their first winter. It also creates an atmosphere of AdultFear for Johnny during the book.

* Grace and her friends (sans Helen) losing the school Dramatic Competition to AlphaBitch Sadie McCall and her group. To make matters worse, they never stood a chance to begin with: despite their great acting, Grace and her team only have old Victorian dresses for costumes and no scenery. In contrast, Sadie has a beautiful painted set and a glittering dress. It’s a scene that can hit close to home for poor readers.

* Earlier in the story, Angela's baby sister, who has been struggling with respiratory issues throughout the book, dies in her sleep. Angela is devastated and begins to blame herself (she went on strike and lost her pay, and she wonders if that money could have made a difference).

* The wagon that Pepper shares with her new husband breaks down en route, forcing the couple to abandon not only the wagon, but virtually all of their possessions, because all the other wagons are already loaded with as much as they can safely carry (in many cases having been forced to leave some of their own items behind) and can't take on so much as a single extra trunk without the risk of overloading them, so there's no way for any significant amount of Pepper and her husband's things to be accommodated.

* The assault on the Lenape village that leads to Caty and Thomas being "rescued". The two of them are dragged away in tears from the people they've come to love as family, and their last sight of the village is as it goes up in flames. The epilogue reveals that, despite their best efforts, Caty and Thomas were never able to discover the fate of the family. They do discover the fate of another assimilated captive, a boy named John [=McCloud=] who is, in all probability, Caty's love interest Snow Hunter (he had once told Caty that he was also born English and his original name was John, and the timeline of his disappearance tracks with what he had told Caty about his past), but it's bad news; John was killed around the same time as the attack on the village. What's more, the epilogue reveals that Caty never married, which seems to suggest that she never got over Snow Hunter.

* The assault on the Lenape village that leads to Caty and Thomas being "rescued". The two of them are dragged away in tears from the people they've come to love as family, and their last sight of the village is as it goes up in flames. The epilogue reveals that, despite their best efforts, Caty and Thomas were never able to discover the fate of the family. They do discover the fate of another assimilated captive, a boy named John [=McCloud=] who is, in all probability, Caty's love interest Snow Hunter (he had once told Caty that he was also born English and his original name was John, and the timeline tracks with what he had told Caty about his past), but it's bad news; John was killed around the same time as the attack on the village. What's more, the epilogue reveals that Caty never married, which seems to suggest that she never got over Snow Hunter.

* The assault on the Lenape village that leads to Caty and Thomas being "rescued". The two of them are dragged away in tears from the people they've come to love as family, and their last sight of the village is as it goes up in flames. The epilogue reveals that, despite their best efforts, Caty and Thomas were never able to discover the fate of the family. They do discover the fate of another assimilated captive, a boy named John [=McCloud=] who is, in all probability, Caty's love interest Snow Hunter (he had once told Caty that he was also born English and his original name was John), but it's bad news; John was killed around the same time as the attack on the village. What's more, the epilogue reveals that Caty never married, which seems to suggest that she never got over Snow Hunter.

** Later, Nancy begins to accept that the woman is her mother, and though she still refuses to leave the plantation for good, she asks another former slave to take her to visit her mother. As the story is told to Patsy, Nancy's mother begins crying TearsOfJoy when she realizes Nancy is willing to keep her in her life.

* In the aftermath of the massacre on the striking men, Anetka witnesses the sheriff and his men not aiding the dead and injured, but ''pointing and laughing at the victims.'' It just really sells how cold and cruel America is to the main characters.

* Nancy, one of the few slaves who [[StockholmSyndrome doesn't want to be free]], rejects her mother when she comes looking for her, and even tells a magistrate that she doesn't remember her mother (that much is likely true) and wants to stay with her mistress. She does eventually start to see the other side; while she never leaves the plantation permanently, she begins paying visits to her mother, who is delighted to the point of tears to finally get a relationship with Nancy.

* The wagon that Pepper shares with her new husband breaks down en route, forcing the couple to abandon not only the wagon, but almost all of their possessions, because all the other wagons are already loaded with as much as they can safely carry (in many cases having been forced to leave some of their own items behind), so even spreading out the items among multiple wagons is impossible because those wagons really can't take ''any'' more weight.

* The death of [[spoiler: Rosalina and Domingo's mother]]], especially Domingo covering her face with roses.

* Hattie's mother is still grieving the deaths of Hattie's four sisters, who died before the story begins. It's a TearJerker when, along the trail, she is [[spoiler: forced to leave behind a trunk of their things--favorite dolls and dresses and other items.]]

* The wagon that Pepper shares with her new husband breaks down en route, forcing the couple to abandon not only the wagon, but almost all of their possessions, because all the other wagons are loaded close to capacity already.

* The epilogue reveals that Jim Sato, who Piper had had a crush on, is killed in the Army trying to rescue the Lost Battalion.

* Pringle and Gideon spend a good part of the book with the Pritchard family, a young couple and their children who they met by chance, and they become close; Pringle even nannies for the Pritchard children. But when Gwen, the mother, realizes that Pringle is the daughter of a mine owner (Gwen's brother was killed in a mining accident), she instantly turns her back on Pringle, even as her husband and (surviving) brother show more compassion. For her part, Pringle is infuriated when she learns that Gwen's brother was involved in the accident that killed her parents (it wasn't really his fault, but Pringle holds him responsible nonetheless). It's bad enough that what was a great friendship was destroyed by incidents that neither of them were directly involved in, but it also means that Pringle was suddenly separated from the children, who she'd practically been raising and had come to love. The epilogue reveals that Pringle never saw the family again, and in fact it's never even confirmed that they survived the fire.

** Even worse, Yolanda’s parents are right: The staff and students ignore or bully Dawnie, and the white parents want her ''dead'' for daring to go to a better school. It’s revealed in the epilogue that Prettyman doesn’t even start enrolling more black children until ''three years'' after Dawnie graduates.

** Worse comes to worse when Mary finds out that their daughter Alice, who it turns out is blind, is being kept as a servant for a wealthy family with a lot of children and that she's poorly treated. Mary has to deliver the bad news to her. Thankfully Alice is taken in by Mary’s friend Sean and his uncle Quinn, and the epilogue reveals that they ultimately got her set up at the Perkins School for the Blind.