The Trouble with Timothy is the third book in the Care Bears book series.
Timothy is an unruly child who constantly disrupts class and is having a bad week at school. When the teacher is giving a math lesson and explaining the concept of addition using apples, she asks what one would get when one adds three apples to two apples, to which Timothy bellows "Applesauce!" and the teacher gets angry at him. Timothy is also disruptive during geography lessons, claiming he will never go to France, Russia, or any of the places discussed. The teacher has had it with Timothy's bad attitude and sends him to the headmaster, the only adult Timothy fears at the school. Timothy is shouted at for his behavior, and disciplined by his parents at home, who yell at him and angrily confine him to his room. Surprisingly, Timothy does not get fresh with his parents, instead doing what they ask of him. His sadness summons Friend Bear, one of the Care Bears, who gets him to open up and cheer him up and make him feel better. Timothy admits his attitude is to get attention, and Friend Bear says that attention is good, but we must discriminate between negative attention, such as getting disciplined, and positive attention, such as getting good marks in school or thanked by our parents. Now encouraged by Friend Bear, Timothy resolves to turn over a new leaf and becomes best friends with Emily, one of the students in his class.
- The title refers to Friend Bear as male, stating that Timothy "picked Friend Bear up by the leg and straightened him up."
- In the beginning, Jennifer's shirt is green. But when Mrs. Pratt yells at Timothy about his paper airplane, it is blue.