This is a page for Greg Heffley's relationships and interactions with the other characters throughout the series.
Rodrick Heffley
The relationship between Greg and Rodrick is complicated and they argue with each other. In Rodrick Rules, Greg had a very embarrassing secret, which was of him accidentally going into the ladies bathroom of Leisure Towers. Throughout the book, Rodrick kept on threatening Greg, saying that he will spill it if he provokes him or tells on him. Rodrick seemed to know that Greg had a crush on Holly Hills in The Last Straw because when they were in a hotel room, Rodrick lied to Greg by saying the Hills family is staying in a room next to theirs. Greg fell for it and Rodrick pushed him out of the door and locked it. Greg was also in his underwear making it even worse for him. Rodrick and Greg are rarely seen getting along, however at the end of Rodrick Rules, Greg and Rodrick bond and end up getting along with each other. Although he did not show it, Greg worried about his brother many times and doesn't want to see him sad. They are shown to work together sometimes when there is a rule they both dislike such making up code words to get away with swearing and misbehaving on weekends along with Manny as well so that Susan doesn’t think Screen-Free Weekends are working.
In the films, their relationship becomes more developed and fleshed out than in the books. The Rodrick Rules movie focuses on them trying to become friends and it succeeds. When Greg accidentally gets Rodrick grounded for the party, Rodrick ends their friendship and starts bullying him again. Luckily, their friendship is restored at the end of the movie. In the Dog Days film, when Rodrick found a Spag Union DVD in the mail, he immediately showed it to Greg claiming they were both in trouble (though it was mostly Greg), Rodrick expressed strong concern for Greg being shipped by their father to Spag Union and advised him to do his best in Wilderness Explorers to make Frank change his mind. Greg also tried to help Rodrick in getting Heather's affections by getting Löded Diper hired for Heather's Sweet Sixteen, which lead Rodrick to happily hug his brother with gratitude, though Greg was annoyed when Rodrick ignored Greg's advice of being dressed in tuxes and to play Heather's favorite music. He also was scared when he thought Rodrick was crushed by the dump truck and was overjoyed to see that he was okay. They are also on somewhat good terms in The Long Haul film.
Rowley Jefferson
According to Greg, Rowley is childish and Greg often takes advantage of him. It was later revealed that when Rowley moved into the neighborhood, he knocked at Greg's door and when Greg opened it, without even introducing himself, he started saying jokes from a book his mother bought him. Greg felt sorry for Rowley and forced himself onto him. Greg has shared his opinions on Rowley's parents, claiming they are overprotective of him. Greg treats Rowley as sort of a slave, making him do all the work and give him piggyback rides. Rowley and Greg's relationship is quite strained as they keep fighting and breaking up, then after a while, they reconcile their friendship such as when he dumped Greg as a friend for his girlfriend Abigail. Greg, despite thinking of himself as a good friend to Rowley, he actually kind of bullies and uses him. In Wrecking Ball when Greg told Rowley about him moving away, Rowley started crying which was annoying to Greg. However, when Rowley gave Greg a present that featured them in several occasions from the past, they both cried, meaning that Greg does care about their relationship (even in the books).
Their relationship is more legit and developed in the films than the books. In the first film, Greg covered up Rowley by claiming to be the one who ate the cheese, when his schoolmates almost found out and begins treating Rowley a lot better. In the Rodrick Rules movie, when Rowley stole the limelight in Rodrick's party, Greg tell his brother he can beat him up in place of Rowley, showing selfless care for his friend. In the third film, he apologizes to Rowley after he messed up again during a family trip.
Manny Heffley
Greg completely despises his younger brother, Manny with a passion, because his parents always treat him like a prince and would give him everything he wants and when Greg and Rodrick were his age, their parents were more strict with them, but mostly due to Manny constantly being spoiled or breaking Greg's belongings, such as inserting a cookie into his video game player, he always gets away unpunished due to his parents's pampered protection. His parents excessively spoil him too as they are never seen scolding him even once, regardless of how much he deserves it.
In Cabin Fever, he switched off all the electricity except the one for his room throughout the electric panel and took all the food and water. While his family was struggling, he was enjoying himself until Greg found out that he did it as he wasn't taught how to tie his shoelaces. He always tells lies and gets away with it like when Greg was playing with Manny in New Year's Eve and found a little piece of thread, he told Manny it was a spider and started pretending if he was making him eat it. Just then Manny slapped Greg's hands and the thread went inside Manny's mouth and he swallowed it and told his mother. He got away by showing his mother it was the size of an orange and Greg was sent to bed early.
He also has imaginary friends that get him out of trouble and make him get extra dessert after dinner. Greg's hatred of Manny is extreme to the point that he will exploit any chances to get back at Manny for revenge, by calling Manny, "Ploopy" the same abusive insult Manny invented during Church in Easter, resulting Manny breaking down crying and Greg left the church with a gloated smile on his face.
Despite his dislike for him, he mentions he actually does feel a little bad for him when a kid scared him by claiming to be a vampire because of his experience with a kid named Bradley who terrorized him when he was around his age and in The Meltdown they are shown to agree on something for once along with Rodrick as all three are shown to dislike Screen-Free Weekends.
Susan Heffley
Susan clearly loves her second son although Greg actually does not get along with Susan as she often embarrasses Greg by calling him affectionate words like "Sweetie", "Sweetie Pie" and "Honey Bunches". Susan always takes Manny aside and she would not tell Manny that his imaginary friends are fake otherwise she thinks he will be traumatized. Greg hates how his Mom never punishes Manny, treats him like a prince and spoils him, even though he changed his password on Net Kritterz, changed the parental control and refused to give the password, and cut power in every room except his in Cabin Fever.
Frank Heffley
Frank thinks that video-games are just a thing to keep Greg away from exercising and he would make Greg eat more and work-out. He also threatened him that he will send him to the military academy, Spag Union if he doesn't shape up in The Last Straw. Greg was also steamed after he stole his and Rodrick's snacks from the pantry due to having a junk food addiction. In Dog Days it is stated that they don't have much in common with the exception of hate for the comic Lil' Cutie.
In the third film, their relationship becomes more complex. Frank tries to get Greg to get off his lazy butt and spend some time outside. To get out of going to Frank's job, he lies about having a job at the country club. When Frank finds out that Greg lied, he stops talking to him and considers sending him to Spag Union. To get Frank's trust and respect back, Greg tries to do better at the scout camping trip. When he sees a rival troop saying mean things about Frank, he comes up with a plan to get back at them. When Greg confesses to his actions, Frank commends him and changes his mind about sending him to Spag Union.
Charlie Heffley
According to Greg, his uncle Charlie brings everything he asked for him on Christmas. However when he asked for a Barbie Dream House when he was younger (thinking it would be a great fort for his toy soldiers), Charlie went and bought the first thing which had Barbie in it, this caused Greg to get a Beach Fun Barbie, and when Greg asked him from Twisted Wizard, he got a photo of himself about the same size as the box of Twisted Wizard. When Greg was little, he used to call him "Red" which was because Greg had red pajamas, however Greg took it seriously. He told his mother about it, and she bought him blue ones, but Charlie gave him the nickname "Blue".
Arthur Heffley /Clyde Heffley:
Arthur/Clyde is the great-uncle of Greg and only says "Muurp" and "Ruup" instead of words, making Greg confused if he is actually meaning something or not, so Greg just takes a response that would be suitable like "No thank you".
Fregley
Greg finds Fregley weird and creepy. Whenever Greg is going to Rowley's house, he always sees Fregley in his backyard, saying creepy things, this causes Greg to go through by going in the gutters. When Rowley broke up with Greg and was hanging out with Collin Lee (his backup friend), Greg thought of making him jealous by having a sleepover at Fregley's. When he went there, he would stay away from Fregley as far as possible. Fregley then apologized to him for chasing him with a booger. In Hard Luck, he accidentally made Fregley very popular and made him win the position in the yearbook as the most popular.
In the films, their relationship is very friendly. In the third film, Fregley shared his history book with Greg after Greg thinks no one brought theirs. He also helped Greg to collect ants for his revenge plan against Stan for insulting Frank and Fregley tried to justify Greg's actions by telling Frank of Stane's insults. However, Greg accepts full responsibility and refuses to let his friends take the punishment for his mistakes.
Chirag Gupta
Chirag is a friend of Greg as he mentions and also a friend of Rowley. The friendship between Greg and Chirag is not shown much. In Rodrick Rules, after he moved away and later came back, Greg would make fun of him with the Invisible Chirag joke. However he later made Greg apologize for it. Other then that, Chirag and Greg's relationship is not seen much despite being portrayed as a friend of Greg.
In the films, Greg's relationship with Chirag was a bit more rivalrous, but they still were friends for some reason. Their friendship is very close as shown in the Dog Days film, Chirag is more than willing to help Greg get back at Stan Warren by setting up a sticky net despite being entangled in the web himself, and when Stan entered his tent with Greg still inside, Chirag sorrowfully said he will always remember Greg for his bravery. When their intentions are exposed, the gang tried to justify Greg's actions, but Greg openly admitted to trying to get back at Stan and refused to have Chirag and the others to take the blame for something he did.
Ben Fielders (Online Book)
Ben Fielders was Greg's old best friend in the online book until he moved away. However he does return and Greg describes about how he and Ben used to have a popular comedy group which many people liked. When he returned, Greg asked him about a girl called Piper Matthews (the online counterpart of Holly Hills). Ben told him untrue things about her, Greg believed him as she was Ben's classmate. When Greg went to the Roll-a-Round, he saw Piper there, Greg was about to go there and ask her to go with him, but when couples skate came, she and Ben paired up, Greg found that Ben just told the untrue things to keep him away from her and that she is actually Ben's girlfriend. Greg got mad and reported on Ben about a bad thing he and Ben did at the church school walls to the church.
Robert Jefferson (Rowley's Dad)
Greg and Robert seem to have a very bad history as Robert always thinks Greg is a bad influence for Rowley and he often tells Rowley to stay away from him. Greg describes him as a very protective parent as he doesn't even lets Rowley play a video game with the slightest bit of violence and won't let Rowley ride scary rides in the boardwalk as seen in Dog Days.
Short Relationships
Dean Delarosa
Greg knew Dean Delarosa when he was in the third grade and was invited to his birthday party, but his mother got the date wrong by a week and Greg ended up coming a week early. Greg liked the gift he was supposed to give him, that he ended up playing with it. Dean was Greg's secret holiday buddy when the kids had to give each other presents anonymously. Greg forgot, but Susan got it and gave it to Greg, Susan didn't knew that it was supposed to be anonymous so Greg and Dean felt embarrassed when the teacher called out Dean's gift's label.
Crushes
Holly Hills
Greg has no relationships with Holly in the book series. In The Last Straw, Greg wanted to impress her because she was, according to Greg, the only girl in his class he liked, who didn't have a boyfriend. However when Greg went to the Roll-a-Round, she called Greg "Fregley". This made Greg lose interest in her. In the same book, Holly wrote in Greg's yearbook and used his real name and said he was okay. Greg was fine with that and started to get interest in her again, but Holly wrote in Rowley's yearbook that he is cute and disappointed Greg.
In the movie trilogy, their relationship is actually more developed than in the books. In the Rodrick Rules film, Greg falls for her when he first runs into her at the roller rink. He tries to sit next to her, but Patty ends up ruining everything. Throughout the film, he tries to impress her, but only ends up making himself look like a fool. At the senior center, Greg and Holly learn more about each other and realize they have similar family issues. Holly even apologizes for calling him, "Fregley." In the Dog Days film, Greg tries to hang out with her, but Heather prevents her from writing down her whole number, so he lies about being a member of the country club to hang out with her. Later, Greg gets Rodrick's band to perform at Heather's sweet sixteen, but they only end up ruining everything and humiliating Heather. Greg tries to apologize, but Holly assures him that it's okay and Heather deserved it. She later holds his hand (implying she may like him back) and has a pool party with Greg and Rowley.
Heather Hills
In Dog Days. Greg had a crush on Heather Hills. He thought that if he would get good with Heather he could get a high school girlfriend (a thing he has been wanting for a long time.) and so he could show off to kids at his school. So then he found that she is a lifeguard at the pool. When they got to the pool Greg would go to the pool which she is lifeguarding on and Greg would exercise in the bathroom so he could have his muscles pop up. Greg thought to impress her he would say anything to a kid doing anything bad (which Heather was supposed to say). Once a kid was feeling bad and he vomited , Heather went to clean it and asked Greg to help her clean it, but Greg just ignored her because he was scared of cleaning the vomit. Soon Greg thought that Heather will soon go to college and that long-time relationships won't work. In the Dog Days movie, Greg doesn't have a crush on her, but in the credits he appears trying to show his muscles to her and her friend.
Natasha
Greg had a crush on Natasha a year prior to The Last Straw. He wrote a love letter to her and made it sound like a posh love letter that his mom thought was unsuitable for his age. He gave it to Natasha, but he was disappointed when Natasha gave him a store-bought card for another friend who was absent. Greg got over her after this.
Abigail Brown
Although not exactly a crush, Greg wanted to have a good relationship with Abigail. He had invited her for the
Valentine's Day dance with Rowley. After some time, Ruby Bird got attracted to Greg, so he quickly ran to Abigail to dance with her but when he realized she had spots, he thought she had chicken-pox and screamed hence hurting her feelings. Rowley later comforts her and walks her to her house and they are heard of as being couples.
Becky Anton
Greg crushing on Becky.
Greg's M.A.S.H.
In Wrecking Ball, it was revealed that Greg had a crush on Becky since 5th grade. On Greg's M.A.S.H., all of the names are Becky on his potential wife list. During Science Class (where they were lab partners), Greg told Becky about his feeling. Becky didn't take it well and asked to be swapped with another student.