Rory Gilmore isn't perfect, as there are many times on Gilmore Girls when she doesn't do the right thing. Sometimes it's hard for her to express her feelings as she's grown up with a fun single mom and always thought it was them against the world. As Rory gets older, she sees that the outside world is a little harsher than she thought.
Lorelai makes some mistakes as a mom, but there's no question that she loves her daughter and wants the best for her, and so do fans of the show. There are some scenes when fans root for Rory and sympathize with her situation, but there are moments when she makes the wrong choice.
Felt Bad: When Logan Cheats On Her
Rory's boyfriend, Logan Huntzberger, cheats on her during a "break" and it's one of the hardest things that Rory has to go through.
This is definitely a time when fans feel bad for Rory, as she genuinely thought that they were taking a time-out from their relationship. She figured they needed a breather to think about their true feelings for each other. She had no idea that Logan wasn't taking it seriously.
Hated Her: When She Gets Too Invested In Jess
When Jess Mariano moves to Stars Hollow, Lorelai is suspicious, Luke Danes suddenly has to become a parent, and Rory is smitten.
Fans don't love Rory's behavior, though, as she starts treating her boyfriend Dean a little worse since she's thinking about Jess all the time. She also becomes really invested in Jess when she should realize that while they like each other, he doesn't have a work ethic and has a lot of growing up that he needs to do.
Felt Bad: When Paris Tries To Make Her Life Miserable
Chilton strikes fear in Gilmore Girls fans as it's not a place for kind-hearted, chill people. Instead, it's a cutthroat academic environment where only the strong survive and no amount of studying is enough. Rory soon learns that she has to step up her game if she wants to do well.
Rory meets Paris Geller shortly after starting at Chilton, and Paris wants to make her life miserable. From giving her bad school newspaper assignments to insulting her in class, not to mention threatening her, Paris could use some etiquette lessons.
Hated Her: When She Lies To Lucy About Marty
Rory's friendship with Lucy happens very quickly at Yale, but a thorn in her side is her existing friendship with Lucy's boyfriend, Marty.
Rory lies to Lucy about the fact that she's been hanging out with Marty for a while now, and it's so weird to see. Fans don't agree with this decision, as Rory should be truthful. This just makes things worse for everyone.
Felt Bad: When She Gets Nervous About Leaving Home
Rory always had eyes on Harvard and ends up attending Yale, and at the beginning of the fourth season, she gets super nervous about leaving home.
This is something that the mother-daughter duo had always planned for, but now that it's here, Rory can't cope. She misses her mom even when she's right there and asks her to stay over the first night. Fans feel bad for Rory as it's definitely tough to leave the nest and be independent, at least at first.
Hated Her: When She Makes Impulsive Decisions About Her Family
Rory knows that her mom has a terrible relationship with Emily and Richard, yet that doesn't stop her from asking them to come to Lorelai's business school graduation at the end of season 2.
Rory often makes very impulsive decisions, and it's not something that fans love about her. She should understand that this makes Lorelai uncomfortable and nervous. It's okay for Lorelai to have a bit of space from her parents during big life events.
Felt Bad: When She Suffers At Chilton
Rory can be a bad friend and when she's not doing well in school or life, it really bothers her and makes her a negative person to be around.
Fans feel bad for Rory when she starts going to Chilton and really suffers. She can't figure out how to get the kind of grades that she did at Stars Hollow High and she doesn't feel comfortable being around her new snobby, wealthy classmates. If anyone deserves to attend a fancy school and get into Harvard (or Yale), it's Rory.
Hated Her: When She Doesn't Talk To Lorelai And Lives With Her Grandparents
Season 6 is a difficult one as Rory starts living with Emily and Richard and doesn't talk to Lorelai.
The Gilmore girls are suddenly torn apart and it's a strange new world. No one roots for Rory during these episodes, as Lorelai doesn't want her to throw her life and academic future away. Rory should listen to her. It's not like Lorelai doesn't sympathize that she's having a hard time or that she's upset, so it would be a fairly easy conversation.
Felt Bad: When She Doesn't Know How To Act When Falling For Dean
Dean is a sweet first love interest for Rory and she definitely acts very innocently when they first meet each other. In the first season of the show, Rory makes a number of adorable mistakes when falling for jo,. She doesn't want to go to Chilton because Dean goes to Stars Hollow High; she freaks out about Dean coming to her house to hang out; and she says "thank you" after he kisses her and steals some cornstarch.
It's hard not to feel bad for Rory in this situation as she's never had a boyfriend before and doesn't have any experience.
Hated Her: When She Doesn't Support Her Mom On Graduation Day
Lorelai's big dream is becoming a business owner and she gets closer in season 2 as she graduates from business school.
Rory doesn't support her mom during this happy occasion, though, and goes to NYC to see Jess. It's not only a strange thing for such a "good girl" character to do but it's pretty cruel, as Lorelai has always been there for Rory. She supported her dream of going to Chilton and even swallowed her pride and asked her parents for money to send her there. Rory should definitely treat her mom better here and respect her accomplishment.