‘Gilmore Girls’ Pro/Con List: Should Rory Be With Jess or Logan?

Kelly Woo
·Writer, Yahoo Entertainment
Milo Ventimiglia as Jess, Alexis Bledel as Rory, and Matt Czuchry as Logan (Credit: Netflix)
Milo Ventimiglia as Jess, Alexis Bledel as Rory, and Matt Czuchry as Logan (Credit: Netflix)

Where the Gilmore Girls lead, we will follow! It’s been nine long years since super mother/daughter duo Lorelai and Rory Gilmore drank all the coffee in Stars Hollow, gorged on junk food and Chinese takeout, fell in and out of love, and dropped every pop culture reference imaginable in their rapid-fire banter. Now, the Gilmores are back to drink even more coffee, talk even faster, and charm us more than ever in Netflix’s continuation of the series, which premieres Nov. 25.

In four 90-minute episodes, titled “Winter,” “Spring,” “Summer,” and “Fall,” Lorelai (Lauren Graham), Rory (Alexis Bledel), and grandmother Emily (Kelly Bishop) all face big changes in their lives. To get ready for the revival, we’re highlighting all the things we love about the show with our official Return to Stars Hollow coverage, from the wacky supporting characters to the insanely clever dialogue to the girls’ complicated love lives. Check back here every day until Nov. 25 to obsess with us over all things Gilmore.

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No topic generates more controversy among Gilmore Girls fans than the question of which boyfriend was best for Rory Gilmore (Alexis Bledel). She had her first love in Dean (Jared Padalecki), the bad boy with a heart of gold in Jess (Milo Ventimiglia), and the rich college boyfriend with a wild streak in Logan (Matt Czuchry).

Gilmore Girls: A Year in the Life, streaming Nov. 25 on Netflix, will likely renew the ’shipper wars, since all three guys appear in the revival series. So, who should Rory end up with? Well, first, we ruled out Dean, because … ugh. Remember how he got married, then cheated on his wife with Rory? And then dumped her again? Dean can keep bagging groceries at Doose’s Market and leave Rory the hell alone.

That leaves Jess and Logan. Both have ardent fans rooting for them, and it’s a tough call. So let’s do as Rory does: make a pro/con list based on qualities that Rory’s true love should have:

Click Image to Enlarge (Credit: Everett Collection/Getty Images/Yahoo TV)
Click Image to Enlarge (Credit: Everett Collection/Getty Images/Yahoo TV)

Romantic

Jess had that slightly dangerous but incredibly charming way about him. He stole Rory’s book — just so he could write notes to her in the margins. And the fact that he looked up how far it was from Stars Hollow to Yale made us melt.

But Logan dazzled Rory with big, sweeping gestures, like buying her a very expensive Birkin bag to surprising her with a rooftop picnic when he was supposed to be in London. He’s such a romantic, he even helped out Luke on Valentine’s Day by letting him have one of his gifts to present to Lorelai. PRO: LOGAN

Literary

Rory is a major book nerd. Aside from coffee and candy, she lives on reading books. She met her book-loving match in Jess, who was reading Jack Kerouac’s On the Road the first time we met him. There was the aforementioned annotating of Howl. He and Rory enjoyed debates about Ernest Hemingway and Ayn Rand. And later, Jess wrote a book and started a publishing house. PRO: JESS

Related: Why ‘Gilmore Girls’ Rejected Ryan Gosling

Adventurous

Rory aspires to be a globetrotting journalist, so her partner should be as spirited and intrepid. Consider how she and Logan first got to know each other: She followed him to a Life and Death Brigade gathering for a story, and he nudged her into jumping off a tower. PRO: LOGAN

Funny

The Gilmore girls love to banter, so any boyfriend of Rory’s has to be able to keep up with witty repartee and deep-cut pop culture references. Jess always had a zinger to pull out, whether it’s joking to a soaked Rory, “I like the new look. It’s very Blue Crush.” Or dressing up in a plaid shirt and backward baseball cap and telling Luke, “I thought this was the uniform.” PRO: JESS

Committed

Rory does not do casual dating (she tried briefly with Logan, but it was a disaster). She wants a steady boyfriend who’s going to stick around. Jess left Stars Hollow without even saying goodbye. And while at first Logan seemed too much of a playboy for Rory, he settled down and committed completely to her. They lived together, and they survived long distance when he was in London. He even proposed marriage to her! The timing and style was wrong, but he was ready to put a ring on it. PRO: LOGAN

Related: ‘Gilmore Girls’: Revisiting The 10 Wackiest Storylines

Encouraging

Rory was always determined to do great things, and she needs a partner who will push her to be her best self. Both Jess and Logan did that, in their own ways. After Rory dropped out of Yale, it was Jess who kicked her in the butt to go back to school. And Logan pulled an all-nighter with her to put out the Yale Daily News. PRO: JESS AND LOGAN

Supportive

Everyone experiences difficult times and situations, and they are made easier by the presence of a loved one. When Rory’s grandfather, Richard, suffers a heart attack, Logan drops everything, borrows a helicopter, and rushes to comfort her in the hospital. His presence there was a stark contrast to the absence of Lorelai’s husband, Christopher. PRO: LOGAN

Family Drama

People don’t exist in a vacuum, and in any relationship you have to deal with your partner’s family. Jess had a big chip on his shoulder thanks to his absent father, and he was sent away by mom Liz because of bad behavior. He wasn’t particularly respectful or thankful to his uncle Luke for taking him in and giving him a job and constantly chafed against any authority figure.

But that’s nothing to the drama Rory had to face with Logan’s family. His terrible mother openly detested her for not being blue-blooded enough, while his domineering father broke Rory’s self-confidence by telling her she didn’t have “it” as a journalist. Worst in-laws ever. CON: JESS AND LOGAN

Related: Ken Tucker on the Importance of the Return of ‘Gilmore Girls’

Intimacy

Sex is a major part of any romantic relationship. Jess gets a black mark on this subject, since he tried to push Rory into having sex when she didn’t want to. Then, he blamed and yelled at her. With Logan, once the relationship was serious, they shared a warm, passionate sex life. She even sexted him! PRO: LOGAN

Lorelai-Approved

Rory’s mom is the most important person in her life. They’re best friends, in addition to being mother and daughter. So Lorelai’s stamp of approval is incredibly important. She never liked Jess much, since he was often disrespectful and rebellious. She didn’t like Logan, at first, either, labeling him a playboy. But after Logan committed to Rory, he went out of his way to earn Lorelai’s approval. He invited her and Luke to Martha’s Vineyard for Valentine’s Day. He spent a day in Stars Hollow. And when he wanted to propose to Rory, he first asked Lorelai for her blessing. PRO: LOGAN

Now let’s tally the results. Both guys have their flaws (deal with your family baggage!), and both have wonderful qualities. But the pro/con list works, and it’s seven in the “pro” column for Logan to just three for Jess. We declare the winner of Rory’s heart to be LOGAN!

Do you agree with our assessment? Take our poll!


Gilmore Girls: A Year in the Life is available to stream on Netflix beginning Nov. 25.