It's safe to say that Rory Gilmore is one of the most popular people in Stars Hollow. The Gilmore Girls character was loved by everyone living in this charming small town, and even when she left to go to Yale, it was always a big deal when she came back to visit.
Although Rory was known for being a sweetheart, she had her moments of doing exactly what she wanted, and sometimes that ended up hurting other people. While unintentional, it's worth noting that Rory still had a lot of growing up to do. Since she flip-flopped between following her own desire and other times, she helped other people, Rory was definitely a complex character.
Shameless: Writing Whatever She Wanted And Insulting A Dancer At Yale
When Rory called out a dancer's weight while writing a review of a performance at Yale, it was definitely tough to watch.
Rory could be totally shameless when writing for the Chilton or Yale school newspapers. She often got carried away, believing that she was going to make a difference with her story, but in this case, she was rude, offensive, and insulting. Rory should have realized that she wasn't an expert on dance and there was no reason why she couldn't have written a more neutral and polite piece.
Proud Of: Befriending Paris Despite Her Harsh Personality
Rory and Paris often appeared to be in competition with each other. If most people put themselves into Rory's shoes, they would have tried to stay far away from this harsh Chilton student, as her delivery was always super intense.
Rory should be proud of the fact that she befriended Paris despite how badly she was treated when she first started going to Chilton. Rory invited her and her friends to a concert and even gave Paris advice about her love life. The youngest Gilmore deserves some credit for being able to tell that Paris was actually a kind person at her core.
Shameless: Taking Ownership Of Dean When He Was Married
Rory seemed to have trouble accepting the fact that Dean married Lindsay — despite being invited to the wedding — and that he was no longer in her life.
When Rory and Dean slept together towards the end of the fourth season, it was because Rory took ownership of him. She didn't care that he was with Lindsay as she felt that he had loved her first. This was shameless and something that Rory should have considered more carefully as it was clear that her romance with Dean belonged back in high school.
Proud Of: Bonding With Her Grandparents Despite Lorelai's History
Lorelai and Emily both had their faults and they never quite got to a good place in their mother/daughter relationship.
When Rory started spending time with Emily and Richard because they were paying for Chilton, she could have kept them at arm's length. It would have made sense if she would have been hesitant to get too close because of her mom's rough history with her parents. Instead, Rory listened to what they had to say and even went golfing with her grandfather. She was open and willing, and this is something that she should be proud of, as it was so meaningful to them.
Shameless: Sharing With Logan That She Liked Someone Else
Rory made a strange choice in the seventh season episode "Farewell, My Pet" when she shared with Logan that she started to like her T.A.. Logan said it was normal to have a crush and they talked about how much they still loved each other.
This was a pretty shameless choice, though, as Rory had no idea how Logan would react. What if he was hurt by that news? What if he even broke things off because he felt that he couldn't trust her? It seemed like a risky move and also a selfish one as Rory just wanted to get it off her chest.
Proud Of: Moving On From Jess When He Bailed On Their Relationship
Jess was the "bad boy" of the show and he made a huge mistake at the end of season 3 when he escaped from Stars Hollow and didn't say a word to Rory.
When she realized that her boyfriend had bailed on her, Rory didn't call him and beg for him to take her back. She tried to put him out of her mind as she was graduating from high school and getting ready for Yale. She moved on from him, and this is something that she should be proud of, as she valued herself and her dreams over a guy who wasn't mature enough to be a solid partner.
Shameless: Cutting Her Mom Out Of Her Life
Season 6 of Gilmore Girls felt so different because the two main characters took a break from each other.
It wasn't something that viewers could imagine as a storyline. But after Rory stole a boat and thought that it was best to leave Yale behind for a little while, Lorelai was so hurt. Rory couldn't see things from her mom's POV and was shameless in cutting her mom out of her life for a few months. She even moved in with her grandparents. This was a truly bad decision on Rory's part.
Proud Of: Going To Sherry's Baby Shower
The season 3 episode "Take the Deviled Eggs..." found Rory attending Sherry's baby shower. Sure, Lorelai ended up coming, too, but it was pretty big of Rory to go to this event.
Christopher wasn't there for Rory and this father-daughter relationship had enough baggage to justify Rory saying no to the invitation. Rory was the more mature person and decided that she was going to support his new partner and their soon-to-be-born baby. This was one example of how polite and mature Rory could be.
Shameless: Flirting With Jess While Dating Dean
While Rory and Dean shared many sweet moments, Rory wasn't always the nicest girlfriend, as she definitely flirted with Jess even though she was attached.
This was one of the most shameless things that this Gilmore Girls character did. She didn't even seem to feel any guilt about it as she was so drawn to the new kid in town and she loved that he was a big reader just like her. It would have been great if Rory had admitted that she didn't feel she had much in common with Dean anymore, but she didn't handle herself in a mature manner here.
Proud Of: Giving Her Mom Tons Of Credit In Her High School Graduation Speech
Rory didn't always make sense, but her Chilton valedictorian speech was absolutely perfect, especially since she both praised her mom and talked about her love of reading.
Rory said of Lorelai, "My mother never gave me any idea that I couldn't do whatever I wanted to do or be whomever I wanted to be. She filled our house with love and fun and books and music, unflagging in her efforts to give me role models from Jane Austen to Eudora Welty to Patti Smith. As she guided me through these incredible eighteen years, I don't know if she ever realized that the person I most wanted to be was her." Of course, this made Lorelai, Sookie, and Luke cry, and it was a flawless moment.