1. Boredom and Lack of Plans: Greg finds himself bored and devoid of any exciting plans for his summer break. He desperately tries to find ways to entertain himself, resorting to mundane activities and getting into trouble.
2. Rowley's Friendship Issues: Greg's best friend, Rowley, becomes distant and preoccupied with his new summer friends. Greg feels neglected and worries that their friendship is drifting apart.
3. Embarrassing Family Situations: Greg's family goes on a disastrous camping trip, filled with mishaps and embarrassing moments. He struggles to maintain a positive image of himself amid the chaos.
4. Work Exploitation: Greg's father makes him work at the construction site with Rowley, but they end up getting exploited and stuck with difficult tasks.
5. The Neighborhood Conflict: Greg and Rowley's neighborhood feud with the older teens escalates, leading to mischievous pranks and conflicts.
6. Romance Troubles: Greg attempts to impress a girl, Holly Hills, but his efforts often backfire, leaving him feeling rejected and humiliated.
7. Misplaced Trust: Greg trust Rowley's scheming brother Rodrick with his most embarrassing secret, only to find that he has been betrayed and his secret has been revealed to the entire neighborhood.
8. The Dog Problem: Greg's attempts to impress his parents by training their newly adopted dog, Sweetie, backfire when the dog becomes unruly and wreaks havoc in the neighborhood.
Throughout the story, Greg navigates these challenges, often making things worse for himself, but he also learns valuable lessons and gains a better understanding of friendship, family dynamics, and personal growth.