- In the first episode, seeing Timothy get picked on by Claude is pretty sad for anyone who's ever been bullied. Especially when Timothy tells his mother that he doesn't want to go back to school due to him getting picked on. Even Yoko expresses sympathy when Timothy gets pushed while trying to protect Yoko from getting hit by a football Claude and the Franks were playing during recess.
- Yoko: That Claude; he's such a showoff and he thinks he knows everything!
- The original 1981 version is even sadder, Timothy is seen near his mother after school and begins crying into her chest and also seen crying alone by covering his eyes.
- The second episode and 1998 book called "Yoko", in which she gets made fun for having sushi for lunch. Later, Miss Jenkins hears Yoko crying alone during recces. The illustration from the book alone is just as heartbreaking.◊
- Miss Jenkins: (hearing Yoko crying and with a concerned expression) I hear one unhappy student in my classroom.
- Later on in the episode, when Miss Jenkins allows the students to try different foods from countries around the world, every student in the class tries the other foods they have except for Yoko. Before the class begins trying the other foods Yoko asks Timothy what he thinks of her sushi. Timothy is about to answer Yoko's question only to get distracted by the other foods being tried in the class. When Timothy comes back to Yoko, he tells her that he didn't get a chance to try the other tasty foods since he's been so distracted. Yoko then responds back by telling him that he didn't try her sushi and walks to a table and sadly tells herself that they should have brought cheeseburgers instead of sushi.Yoko: And you didn't even try my sushi, not even one piece.
- This ends up as a Heartwarming Moment, since after Yoko says that to herself, she hears Timothy grab two chopsticks attempting to try her Sushi. She then walks up to Timothy and tells him how to use chopsticks. When Timothy sees Yoko using chopsticks, he decides to grab one of Yoko's sushi and eats it and he really loves it.
- In "Friends Forever" where Yoko is continually unable to play with Timothy due to her ballet practice, and on the one day she is available, Timothy, assuming she wouldn't be, had already scheduled a playdate with Charles.
- When Timothy misunderstands the letter and what Yoko said on the phone the other day. He once again asks Yoko if they can play but reveals that she once again has to practice with Grace. He then tells her that he thought they were going to play and Yoko hears Grace to hurry up then looks a bit sad and apologizes to Timothy before heading off with Grace.
- In "Lifesaver Lilly", the title character lays on her bed realizing that she's too forgetful to take care of the school's pet fish, saying those words in a very serious and monotone sounding voice, contrasting with her normally upbeat and optimistic mood. After, Lilly actually thinks she lost her own fishbowl which had her pet Treasure. She gets scared and runs to her mother crying, but her mother tells her that she's only cleaning the fishbowl. Lilly's voice really shows how scared she is knowing how much she cares about her pet.
- Lilly: Mama! Mama! I lost Treasure, I lost Treasure! *starts crying into her mother's chest*
- In the episode "Talent Show", where the school is hosting a talent show. Grace is practicing for her own ballet dance to show to the audience. The next day the students are wondering why she's late. They get surprised when they find Grace walking on crutches complete with a sad and broken expression. The students ask her what happened to her foot. She tells them that she's sprained it and starts crying when she tells the students that she won't be able to be a part of the show.
- Juanita's insecurity and shyness, as well as her feat of her mother leaving, are pretty sad to watch. At one point, Miss Jenkins even starts to feel very sorry for Juanita because of how lonely she is due to her difficulty interacting with the others (she doesn't know how to build a moonbase to play with Fritz, or how to jump double Dutch to play with Grace and Nora).
- The original book version of "Make New Friends" has Yoko instead of Juanita, and mentions that she actually cried out loud making everyone upset when her mother left.
- "Two Tutu Friends": Doris and Grace's argument where they call each other names, Grace being embarrassed, the two ignoring each other after practice, and finally making up with Grace crying a bit. At the start of the episode, Grace teaches Doris some ballet moves. The ballet recital starts out very good until Grace accidentally trips and falls near the hangers that held other tutu dresses. Doris ask her if she's okay and is seen crying briefly and tells her not to tells the other students about the incident. The next day during lunch, Doris is telling the other students about how "funny" Grace looked when she fell. Grace walks in and starts crying and calls out Doris. Making the situation worse is when Grace calls Doris a blabbermouth; in turn, Doris calls Grace a crybaby, and then they ignore each other. After the second ballet practice, Doris and Grace decide to talk to each other and apologize.
- While the episode "Don't Lose It, Lilly" was mostly lighthearted and funny, the moment where Charles discovers that Lilly ate the other ice cream cone (which starts melting in her right hand) that she was going to give him is pretty sad to look at. Especially the hurt expression Charles makes during that scene (see the page image).
- In the episode "You're Invited", Doris thinks that she didn't get invited to Lilly's birthday party due to her behavior and remembers her previous statements on Lilly's forgetfulness as seen in flashbacks from previous episodes. She feels very guilty and attempts to make up for her actions and tries being more friendly around her. Timothy and Yoko try giving her some good advice on being kind around Lilly. Unfortunately, this doesn't work out (she ruins Lilly's orange tree painting and gives her a sandwich with mustard, which Lilly dislikes). However, it ends up in a happy note, Doris was invited and attends the party after finding out her brothers had accidentally left Lilly's invitation under the mailbox.
- In the episode "The Taketombo", after the Franks break Yoko's taketombo, Yoko answers Miss Jenkins's questions about what happened to it by nodding and shaking her head in silence. She even cries in the episode. Yoko was going to have it as part of the class's "In The Spotlight" when she told Timothy on their bus to school. But Miss Jenkins later announces to the class that they won't have "In The Spotlight" due to the incident. The entire time, Yoko is basically in shock about what happened◊ and doesn't say a single word for the rest of the episode until the Franks along with their father decide to have a meeting in Yoko's house with her and her mother. The Franks start feeling very guilty for what they've done when they return home. They feel so bad that they refuse to eat their beans during dinner, despite it being their favorite.
- After Miss Jenkins cleans up the broken taketombo, Grace and Timothy call the Franks out on their actions. Timothy's reaction to Yoko crying in class is the most notable since he and Yoko are best friends and you can tell that he's very disappointed in the two knowing how kind and sweet she is. He knew she didn't deserve that to happen, especially since Yoko allowed him to be the only student to see it as a preview for "In the Spotlight" on the bus prior to the incident.
Tear Jerker / Timothy Goes to School
Yes, even though this show is mostly sweet and harmless. The show still manages to show some heartbreaking moments with the characters.