The book opens describing Greg's worst summer ever beginning with Greg Heffley and Rowley Jefferson going to Rowley's country club after school closes for the summer, but Greg is kicked out because he complained of even the smallest predicaments. The beach trip that he was looking forward to is canceled because the Heffleys don't have any money; the Heffleys resort to going to the town pool, which Greg dislikes because of its hairy and rotund visitors.[1]
Later, Greg and Rowley have a sleepover together, and watch a horror movie taken from Rodrick's room. After the movie, Greg and Rowley soon became paranoid on account of a muddy hand that might kill them, which was in the movie. Unfortunately for Greg, his mother, Susan realises that he and Rowley watched the horror movie after Greg's father told her when he found them sleeping in the bathroom. And then she starts a reading club in which he is the only participant after two days. The reading program, however, is put to a stop when Mr. Jefferson arrives with a huge bill that Greg and Rowley spent on fruit smoothies at the country club, and he forces Greg and Rowley to pay it off.[1]
Greg and Rowley decide to do a lawn care service to pay the debt, but Mr. Jefferson only makes them one flyer for their business, after he tells them they can't use his computer. Their first customer is Mrs. Canfield, who lives on Greg's grandmother's street. Unfortunately, the job ended as a fiasco when the boys never used a lawn mower before, all the gas leaks out of the mower, and the instructions are in Spanish. When Greg tells Rowley he has to do most of the work while Greg counts the money, that made Rowley annoyed and he quits. Greg mows Mrs. Canfield's lawn by himself, but she refuses to pay him because he didn't mow all of her lawn because of the dog poop on there.[1]
Greg’s birthday soon arrives, but the gifts he receives are all gifts he loathes, including a useless cellphone that only calls home and 911. This is because Greg's parents believe that he, like his older brother Rodrick, will just rise the bill up if he gets a regular cellphone. Greg gets money in every card he receives, but Susan, his mother, confiscates it to pay off Mr. Jefferson. Uncle Joe’s dog, Killer, devours much of Greg’s cake, thus "ruining" his birthday. The following day, he and Rodrick both get fish as a makeup gift, even though it wasn't Rodrick's birthday, which Greg said was "unfair". However, when the family takes a trip to a water park, Rodrick's fish eats Greg's fish after Susan puts Rodrick's fish in the same bowl because Rodrick didn't feed the fish or clean the bowl once and was starting to feed off the algae growing on it.[1]
The next day is Father's Day, so the Heffleys visit Leisure Towers to spend the day with Greg's grandfather. There, Frank tells of how his dog, Nutty, ran away to a butterfly farm. Greg's grandfather then explains that he had actually run the dog over and Greg's father takes off in annoyance. He then buys a dog which Susan names "Sweetheart" and shortens to "Sweetie", even though the dog is actually male. Even though Greg has wanted a dog for a long time, he quickly becomes annoyed at Sweetie, who naps on his pillow, sleeps on his bed, and won't stop barking at the television, and the only way that gets him to stop barking is when a commercial with gophers popping out of their holes comes up.[1]
Greg's mother keeps making Greg go to the town pool with her and Manny, which Greg agrees to only to hang out with Heather Hills, who is a female lifeguard there. Greg tries to make a good impression to her, even though she barely pays any attention to him. One day, Greg decides to end the so-called "relationship" when he makes her clean a kid's vomit and was too sick to clean it himself after he had to save Manny from the naked shower people.[1]
The Jeffersons later invite Greg to go to the beach with them, which is where Greg had wanted to go, but he realises it wasn't what he expected, where he begins to have a breakdown from no electronics, almost got jumped by teenagers he pulled a prank on, and especially the Cranium Shaker, which almost makes Greg vomit. He tries to entertain himself, but he is sent home after he snaps a rubber band at Rowley.[1]
Susan later tries to get Frank and Greg together, but both of them realise that they should keep their distance. She even got them tickets for a baseball game, but Greg thought Frank was trying to get rid of him for the incident that happened earlier, and calls the police on him, only embarrassed to discover the truth. To get out of it, they had to give the two cops their tickets. However, they both hate much of the same things, such as a comic named Li’l Cutie, where the writer has retired and passed it on to his son (who was possibly the basis of the character when he was little) and has made the comic even worse. Later, Sweetie is given to Greg's grandmother for company after her old dog Henry died.[1]
The book ends with Greg realizing that summer is over when he sees a photo album titled "Best Summer Ever!" It is a "horrible record" of that summer to Greg, but Greg writes that the person who had taken the pictures had told the story.[1]
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