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Which boyfriend did Rory love the most?

Jess Mariano, with his understanding and respectful relationship with Rory, is considered her number one boyfriend due to their ability to still love and respect each other after breaking up.
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Who is Rory true love?

Logan Huntzberger

He brings her to secret society parties, makes grand romantic gestures and eventually becomes less of a playboy. Logan is Rory's main relationship in university, and while Rory made Logan a better person, their relationship sometimes feels one-sided.
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Who does Rory Gilmore fall in love with?

In season 5, Rory and Logan fall in love, which definitely surprises them both. Logan didn't think that he would want something more than just a casual relationship, and Rory isn't looking for anything serious after breaking up with Dean.
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Did Rory love Logan more than Jess?

It was the most mature grown up relationship she's had. You can always see the love between them, even in the revival. I agree it's Logan she loved most, but for different reasons. Even though I'm a die-hard Rory & Jess shipper, they weren't together long enough for her to really love him.
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Who did Rory lose her virginity to?

Rory Loses Her Virginity To Dean

Rory has sex for the first time with Dean in the season 4 episode "Raincoats and Recipes." This changes their relationship, as after being exes for a while, they're now in a strange place where they realize they still share an attraction and real feelings.
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ranking all of rory gilmore's love interests

Does Rory cheat on all her boyfriends?

Rory cheated on almost every single one of her boyfriends, except Jess. However, she did cheat on Logan with Jess — unbeknownst to him. During a fight with Logan, Rory went to Jess in Season 6, Episode 18 and kissed him.
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Whose marriage did Rory ruin?

I often see posts and comments about how Rory was the absolute worst for 'breaking up' Dean's marriage, and I won't explain my belief that someone else can't break up your marriage in case you ask them or let them any further, but I honestly wish people could allot more of the blame to Dean and actually hold him ...
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Did Jess ever love Rory?

Not only does Jess tell Rory he loves her in season 4, but he also offers for her to come with him to New York. Both times, Rory and Jess still end up going their separate ways.
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Why does Rory dump Jess?

The two broke up when Jess ran away for a new beginning with his dad in California — completely ignoring Rory's feelings. After not seeing each other for years, Jess showed up at the Gilmores where he asked Rory out to dinner to talk about his new book.
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Did Logan really love Rory?

Definitely yes. Even at the very beginning, Logan is so invested in Rory that he's willing to date her, despite him never having done that before.
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Did Rory ever date Tristan?

It's true that Rory and Tristan never officially dated, and she continued her romance with Dean, but what if Rory had made a different decision? When thinking about Rory's love life, it's interesting to compare Tristan and Dean.
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Did Rory ever love Dean?

Rory drops significant hints (like at the town meeting) that she misses Dean and really does love him, resulting in him turning up at Chilton where Rory tells him that she loves him ("Dean!" "What?!" "Stop!" "Why?!" "Because I love you, you idiot!") and they get back together.
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Was Lorelai jealous of Rory?

Lorelai's Jealousy Over Rory And Her Parents

This wasn't something that Lorelai was expecting and she took her jealousy out on Rory. Since Lorelai never had that kind of relationship with her dad, she hated that Rory was getting close to him.
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How many boyfriends has Rory Gilmore had?

Throughout Gilmore Girls' seven seasons, Rory had four boyfriends, with three of them serious: Dean Forester, Jess Mariano, and Logan Huntzberger.
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How many boyfriends did Lorelai Gilmore have?

Besides an on-again, off-again relationship with Rory's father, Christopher Hayden, Lorelai had a few romantic relationships that included Max Medina, a teacher at Rory's school, Chilton, to whom she was briefly engaged; Alex Lesman, an outdoorsy coffee house entrepreneur; Jason Stiles, a childhood acquaintance, and ...
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Who does Dean end up with?

Over the years, the series' fans have debated every aspect of the show. Still, there are only a few storylines that are universally disliked. Dean Forrester's marriage to Lindsay Lister is one of those storylines.
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Did Jess cheat on Rory?

Jess Never Cheated On Rory

Furthermore, while Rory is something of a serial cheater, she never cheats on Jess, either. She did cheat on both Dean and Logan with Jess, which is not great, but it proves that she was happiest with him and couldn't resist coming back.
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When Rory kisses Jess?

I Can't Get Started (Season 2, Episode 22)

It's the episode that makes it clear Jess isn't going to pretend he doesn't have feelings for Rory and that it's going to be impossible for her to just push him away in favor of Dean. After a lot of build-up, the two finally kiss.
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Did Jess get Rory pregnant?

Although Jess reunites with Rory in the revival, there is no indication of a recent romantic encounter, making it unlikely that he is the father of her baby. While Logan may be the biological father, Jess is likely to be Rory's long-term romantic fate, but their relationship poses challenges due to family dynamics.
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How long were Rory and Jess together?

On Gilmore Girls, Bledel's Rory Gilmore dated Ventimiglia's Jess Mariano for several months. Unfortunately for Team Jess fans, their relationship didn't work out, as Jess left town shortly before Rory went off to college. Ventimiglia and Bledel's relationship in real life, however, lasted much longer.
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Does Rory end up marrying Jess?

Rory doesn't end up with Jess, Logan, or Dean, who is married with three kids and a baby on the way. She ends up with a baby. Needless to say, it made for a polarizing ending that fans have been picking up for a while. Watch "Gilmore Girls: A Year in the Life" on Netflix now.
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Why did Jess leave Gilmore?

His leaving Stars Hollow in Gilmore Girls season 3 was perhaps not entirely unexpected – Jess needed to find and connect with his father before he could figure out who he was and whom he wanted to be. But in doing so, he ran away from those who truly did care about him, flaws and all.
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Who does Dean marry in Gilmore?

Dean subsequently begins dating Lindsay Lister (played by Arielle Kebbel). Dean appeared less frequently on Gilmore Girls starting in Season 4, as he eventually married Lindsay.
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How old is Rory when she gets pregnant?

In Gilmore Girls: A Year in the Life, Lorelai is 48 years old for the majority of it, while Rory becomes pregnant at 32.
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Why did Gilmore Girls end?

Back in 2007 when the show ended, Variety reported that the decision came down to a contract negotiation: "Money was a key factor in the decision, with the parties involved not able to reach a deal on salaries for the main cast members.
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