Gilmore Girls: 5 Most Romantic Rory & Jess Scenes (& The 5 Most Awkward)

Fans of Gilmore Girls enjoy talking about Rory’s romantic prospects, whether they find themselves on Team Jess, they loved her relationship with Dean, or they were thrilled to see her with Logan in the revival. Jess had a big impact on Rory’s life and whenever she ran into him years after their break-up, she appreciated his wisdom and approach to life.

While Dean could sound sweet and romantic at times, there was something special about Jess. From his rebellious personality to how much he loved bantering with Rory, he was a special character. While Jess and Rory shared some heartwarming moments on Gilmore Girls, they also had some less than romantic times.

10 Romantic: Jess Bought Rory’s Picnic Basket

What’s more romantic than enjoying a picnic lunch? While Rory and Jess weren’t dating when they had a picnic in season 2 of the show, they did experience more sparks than they might have anticipated. Jess bought Rory’s picnic basket, which naturally upset Dean, who thought he would be the one to share it with his girlfriend.

It’s hard to choose between Jess and Dean as Rory’s best love interest, but there’s no denying that in this scene, the two characters realized how much they cared about each other.

9 Awkward: Jess Found Rory’s Bracelet

While Dean and Lindsay had some good times, their relationship was nothing compared to the young romance that he shared with Rory. He gave Rory a bracelet, which was the first time that she realized how well things were going between them. In season 2, Rory got really upset when she lost the bracelet, and it turned out that Jess had it. It doesn’t seem like Jess was aware that Dean gave Rory this bracelet and that it was so special to her, and this was a really awkward moment on the show.

Lorelai told Jess that it was really mean to steal the bracelet and Jess made things even worse by being super blunt: “If it’s the most precious thing she owns, why did it take her two weeks to notice it was gone? You might want to reevaluate how madly in love she is. I wouldn’t start calling him son yet.”

8 Romantic: Rory Realized That Jess Felt She Was Special

When Rory asked Jess, “Why are you only nice to me?” they both realized that he cared about her a lot. This was a huge deal, as Jess was new to Stars Hollow and everyone thought he was going to cause trouble.

Rory was right in pointing out that Jess could be really rude to anyone he spoke to, including Luke, who was just trying to help him find his footing at this point in his life. Jess saw something special in Rory and he loved being around her. He would do anything for her and he wanted to talk to her as much as possible. It doesn’t get more romantic than that. Rory read several books on Gilmore Girls and in seasons 2 and 3, she and Jess bonded over how much they loved to read. It was so romantic that they had this shared interest.

7 Awkward: They Never Had A Real Break-Up

It definitely wasn’t Jess’s finest moment when he left Stars Hollow and didn’t explain to Rory what was going on. He didn’t even break up with her or tell her anything at all.

Rory felt awkward and embarrassed that her boyfriend couldn’t muster up the courage to tell her it was over. She had defended Jess and told everyone that she saw a side of him that they couldn’t, and this was how he treated her. When Rory answered her phone at her Chilton graduation, she could tell that Jess was on the other line but that he wouldn’t talk to her, and she felt terrible.

6 Romantic: Rory Had A Nickname For Jess

It was adorable when Rory called Jess “Dodger” and when he was confused for a minute, she said “Figure it out.” He realized that she was making a reference to Oliver Twist.

Rory and Dean didn’t have as much friendly and flirty banter as Rory and Jess, and they were missing nicknames and inside jokes. These are the things that help people bond even more, especially at the beginning of a relationship. From this simple word, it was clear that these two would end up together.

5 Awkward: Rory Visited Jess In New York City, Missing Her Mom’s Graduation

Lorelai worked hard toward opening her own inn and that included attending business school. But when she graduated, Rory was nowhere to be seen.

She visited Jess in New York City, and this was out of character for her, as she was always a great daughter who could be counted on. Missing her mom’s big day would always be awkward, but missing it for Jess was even worse, as it proved what everyone in Stars Hollow thought: that Jess was an awful influence.

4 Romantic: He Told Her To Write A Book About Her Life Story

When they met up in the Netflix revival A Year In The Life, Jess told Rory to write a book about her life story. Jess always believed in Rory’s writing and that was super romantic. While Dean and Logan loved how smart Rory was, they didn’t support her in the same way.

Jess always wanted Rory to listen to her heart and forget about what society or her family was telling her. This was important, as she wanted to make other people happy.

3 Awkward: They Kissed At The Wrong Time

While many first kisses on TV dramas are romantic and cinematic, that wasn’t the case for Rory and Jess on Gilmore Girls.

They kissed at Sookie and Jackson’s wedding, and it couldn’t have been a worse time or place. This was awkward, especially since Rory was still dating Dean at the time. If she had broken up with Dean before kissing Jess, it would have been much better, but this became a messy and complex situation quickly.

2 Romantic: He Said “You’re Still A Contender”

It was exciting to see Jess back in Stars Hollow in the revival, and when Rory said that she felt like she had no clue what she was doing with her life, he was incredibly supportive.

Jess said “you’re still a contender” and fans swooned, as this couldn’t possibly get more romantic. Viewers had wondered if the two characters would reunite in these new episodes, and while they didn’t get back together, it was hard to view their conversations as merely platonic.

1 Awkward: Jess Had A Black Eye At Friday Night Dinner

There are several great Friday Night Dinner episodes and it was tough watching Emily invite Jess for this Gilmore ritual. Jess had a black eye and it seemed like it would have been better to bail on the evening than show up and let Emily see him in this state.

Of course, this dinner went terribly and Jess went home pretty quickly. Rory was embarrassed and knew that her grandmother wouldn’t understand why she was in a relationship with Jess. There was no way for Jess to redeem himself in Emily’s eyes, and it was awkward that Emily couldn’t see the good in Jess.

About The Author

Aya Tsintziras
(1738 Articles Published)

Aya Tsintziras is a freelance writer who writes about pop culture and TV. She has a Political Science degree from the University of Toronto and a Masters of Journalism from Ryerson University. She loves coffee, reading, working out, and watching TV. She lives in Toronto with her husband.

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