The bond between Lorelai and Rory Gilmore is what made Gilmore Girls one of the most memorable TV dramas of the early 2000s. The two women grew up and learned from each other's failures and achievements — including in the romance department.
Rory didn't grow up with a stable father figure in her life and never got to see how functional relationships worked at home. This proved itself in many of Rory's relationships with the men in her life. While Rory wasn't always to blame for her relationship woes — the men made their mistakes too — she didn't always make it easy for the partners she's had over the years.
10 Best: She Encourages Them To Do Better
Rory expects the men she dates to have the same expectations for themselves as she does for herself. From a young age, Rory wanted to go to Harvard and made that clear to both Dean and Jess when she was dating them in high school. As fans know, Rory ended up going to Yale but she still had high expectations for her future and never lost her focus.
When Rory dated Dean, she encouraged him to focus on higher education and was upset when Lindsay essentially forced him to drop out. With Jess, Rory pushed him to go to school to make something of himself. And when Rory dated Logan, she inspired him to commit to one person and to keep his eye on the prize regarding work.
9 Worst: She's A Horrible Communicator
To be fair to Rory, she didn't have the best examples of open and honest conversation while growing up. Lorelai had a hard time being honest with herself — and her partners — and her grandparents didn't know how to communicate with Lorelai without screaming or bribing. This caused an issue for Rory's future.
She scrambled to find the right words for Dean when he told her he loved her, she wasn't honest with herself when she started having feelings for Jess while with Dean, she wasn't open with Dean about being too clingy, and she didn't even know that she and Logan broke up. When it comes to communication, Rory definitely needs improvement.
8 Best: She Remains Independent
It's impressive that no matter how many men Rory dated, she always stayed true to herself. She enjoyed her me time and looked forward to her independence. She was just as happy reading her books alone in her bedroom as she was on a date with one of her partners.
As different as the men Rory dated were, she never lost sight of herself — except for that time she stole a yacht... In fact, she was so independent that she chose her career over Logan's proposal, even though she was in love with him.
7 Worst: She Literally Forgot She Was Dating Someone
It felt out of character for Rory to forget that she was dating a man in the reboot, Gilmore Girls: A Year in the Life. His name was Paul and they were apparently together for over a year. The only problem was that he was so boring that Rory literally forgot about him.
She would leave reminders for herself to break up with him and never would. Poor Paul even drove to Stars Hollow to spend the weekend with Rory and her mother only to find out that Rory didn't remember he was coming.
6 Best: She Gets Along With Everyone
It's always nice when your significant other gets along with your friends. It makes life that much easier. For Rory, the only two friends she needed her boyfriends to get along with were Lane and Paris. But Rory deserves some credit when things were the other way around.
Rory was seen being friendly with Dean's roommate after he moved on from Lindsay but the best example is Logan's friends in the Life and Death Brigade. Rory became an unlikely friend of Logan's squad and was still friendly in the reboot.
5 Worst: Cheater, Cheater
Rory demands respect in her relationships but she doesn't always reciprocate. She has cheated on her boyfriends and lied to them when she didn't want to face her feelings. She kissed Jess when she was still dating Dean, she fell in love with Jess while lying to Dean's face, she kissed Jess when she was arguing with Logan, and don't forget about all of the lies she's told in the past to cover up her whereabouts when she didn't want her partner knowing the truth. If one thing is true, it's that Rory has a hard time being honest with herself in her relationships.
4 Best: She Can Cope With Long Distance
Long-distance is not for the faint of heart. In order to make a long-distance relationship work, one needs open and honest communication. And sadly, Rory isn't good at either of those things. However, she did a shockingly good job when she was put to the test.
Rory proved to be a good long-distance girlfriend when Logan was in London and she proved herself again when she was at Yale and Dean was in Stars Hollow. Being in a long-distance relationship gave Rory the independence she craved and the adoration she enjoyed.
3 Worst: She Compares Boyfriends To Each Other
Rory was young and naive when she started dating Dean. It makes sense that she would compare future boyfriends to him because Dean was all she knew. But this was unfair.
She often compared how Jess treated her to how Dean treated her. At first, Rory loved how much space Jess gave her but it soon became too much space. She missed being fawned over and protected like the way Dean made her feel. As much as Rory liked Jess, he didn't stand a chance if she was going to hold him up to her ex all the time.
2 Best: She's Forgiving
Rory deserves some credit for being able to move on and start fresh time and time again. Unlike most teenagers, Rory didn't hold grudges or pick fights to make a partner jealous. She was always comfortable in her own skin. She could have been resentful of Logan plenty of times throughout their relationship but always started with a clean slate. This could be something she learned from her mother, who had constant ups and downs with Christopher but never held things against him.
1 Worst: She's Not Honest With Herself
Rory is a brilliant and forthcoming young lady who doesn't hold grudges and loves her independence, and yet she lies to herself constantly. When she was dating Dean, Rory told herself that Jess was just an annoying friend of hers that she couldn't quit. She refused to admit that she had feelings for him until Dean broke up with her over it. It was then that Rory came clean with herself and admitted to liking Jess.
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