This is a page for Greg Heffley's relationships and interactions with the other characters throughout the series.
The relationship between Greg and Rodrick is complicated and perhaps the most important one. They tend to fight and argue with each other. In Rodrick Rules, Greg had a very embarrasing secret, which was of him accidentally going into the ladies bathroom of Leisure Towers. Rodrick throughout the book kept on threatening Greg that he will spill it out 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. Although they tend to fight a lot and will not show their feelings openly, they love each other more than anything else. Rodrick and Greg are rarely seen getting together, 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 worries about his brother many times and doesn't want to see him sad.Greg. He is childish and Greg doesn't rely on 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 a little bad for Rowley and forced himself to befriend him. Greg also shows how much Rowley's parents are overprotective of him. Greg treats Rowley more of a slave by making him do all his work, carry his bag and give him piggy rides, be his campaign manager and when Rowley becomes the social chairperson in the Third Wheel, Greg thinks that he will boss over Rowley and tell him what to do. In the movie Greg doesn't seem to do things like that to Rowley, treating him more of a best friend, but still keeps giving his advices to Rowley. 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 of Rowley, he actually kinds of bullies him ( like playing pranks and jokes on him) and also uses him ( once made him give Greg a piggy-ride, writing Greg's english work as Greg can't write in cursive and making him scout for dog defecations ).
Greg does not get along with his younger brother, Manny, 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. His parents seem to spoil him too as they are never seen scolding him even once. In Cabin Fever, he switched off all the electricity except the one for his room throughout the electric panel. 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. His friend is Mikey as of Hard Luck. This makes Greg feel bad since he doesn't have any friends.
Greg actually does not get along with Susan as she often embarrases Greg by calling him 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 and 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 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.
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 Barbie doll, 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/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". In the Rodrick Rules film, after Greg doesn't tell his parents about the party Rodrick held, they became friends and Greg would be helped by Rodrick in many circumstances and given advices although the relation sours after Greg uploads the video of Susan dancing and it gets popular.
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 the film, Fregley chases him with a booger instead. In Hard Luck he made Fregley very popular and made him win the position in the yearbook called Most Popular.
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.
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.
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.
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 which he liked and didn't have a boyfriend. However when Greg went to 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 OK. 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 series though Greg and her may have become a couple at the end of Dog Days (Movie).
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 has a crush on her, but in the credits he appears trying to show his muscles to her and her friend.
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.
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 runs off with her and they are heard of as being couples.