* Greg's plan to be "cool" backfires: He tries various schemes to become popular, but his efforts often make him look even more awkward. His attempt to appear tough by pretending to be friends with the school bully, Rowley, ends up backfiring spectacularly when Rowley gets hurt and Greg is blamed.
* His attempts at "social media" are disastrous: Greg's attempts to make a "cool" video for his classmates result in embarrassing fails. His efforts to "go viral" only highlight his awkwardness.
* His quest for a girlfriend goes awry: Greg dreams of having a girlfriend, but his attempts to impress girls often end in humiliation. He ends up with a crush on Rowley's sister, who is far from his ideal, and even that relationship doesn't go smoothly.
* His desire to "fit in" separates him from his friends: Greg's constant quest to be popular and "cool" often leads him to neglect his genuine friendships, particularly with Rowley. He becomes embarrassed by Rowley, even though Rowley is actually a good friend.
* His attempts to impress his father are met with disappointment: Greg constantly tries to please his father, but his efforts are often misinterpreted or dismissed. His father's lack of interest in his "cool" hobbies and aspirations creates a rift between them.
These situations showcase the irony of Greg's experiences. He tries desperately to control his environment and create the life he wants, but the world seems determined to throw him curveballs. His attempts to navigate the social landscape of middle school often lead to unexpected and humorous outcomes.