Who was Rory's best boyfriend?

1. Logan Huntzberger
There are so many reasons why Logan is at the top of this list. Logan started off as a guy who just dates around with no commitments. But, when Rory admitted she didn't want to be casual, he was willing to be in a committed relationship for her.
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Who was Lorelai's best boyfriend?

Max Medina was arguably one of her better boyfriends and eventual fiance. Out of all the men that Lorelai dates, Max had Lorelai's best interest at heart. He's kind, smart, sensitive, and always willing to do whatever Lorelai and Rory need him to do.
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Who was Rory's first love?

Although moving schools, Rory started to like Dean back, and he became her first kiss and, later, her first boyfriend. The duo had a brief breakup at the end of season 1 when Dean told Rory he loved her and she didn't say it back.
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Who were Rory gilmores boyfriends?

Across the seven seasons Rory has three serious boyfriends – Dean, Jess and Logan. They all have their strengths and a lot of weaknesses. However they're not the only men Rory is interested in. Throughout the series Rory goes on a number of dates and experiences multiple flirtations with a number of different guys.
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Who was Rory's soulmate?

While Logan might not be everyone's favorite Rory-boyfriend, he was definitely her most serious on Gilmore Girls - and these moments show why.
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ranking all of rory gilmore's love interests



Why Jess was the best for Rory?

He was only able to connect with Rory through their animated discussions and love of books. Jess slowly worked his way into Rory's life as he worked at Luke's Diner, always popping in at the perfect time with a quip about the town's quirkiness or whatever book Rory was reading.
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Was Logan a good boyfriend Rory?

With a total of 83 out of a possible 120 points, Logan is statistically Rory's best boyfriend. This may come as a shock to many in the Gilmore Girls fandom, where Logan is quite the divisive figure. But while Logan undoubtedly has his faults, it's clear he's also the most well-rounded of the bunch.
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Does Rory sleep with Jess?

The tragic history of Jess and Rory is not necessarily that they never consummated their relationship, but that that their relationship was never as serious as it would have needed to be to last. They may be right for each other, but timing and emotional self-destruction got in the way.
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Does Rory date her TA?

Alright so Rory never dated her hot TA, but she was really into him for like one or two episodes. In all fairness, if they did ever go out it probably would've been a pretty good relationship, so it's for the best.
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Who was the worst boyfriend for Rory?

Jess Mariano

The fact that he was the "bad-boy" from out of town and only cared about Rory makes him such a great character. He felt so guilty when they got into the car crash and was STILL there for her.
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Which Gilmore guy is the best?

1. Luke Danes (Scott Patterson) Despite being someone who's very set in his ways, Luke is always willing to adapt for the people he cares about.
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Who is the first person Rory sleeps with?

4 Season 4: Rory Loses Her Virginity To Dean

Rory has sex for the first time with Dean in the season 4 episode "Raincoats and Recipes." This definitely 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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Does Rory cheat on Jess?

Rory cheated on Dean with Jess, and still managed to string him along for several more episodes before ending up with Jess. Paris cheated on her boyfriend, Jamie, and ended up in a relationship with the professor she was cheating with.
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Why did Rory reject Logan's proposal?

Rory made the right choice when she said no to Logan's marriage proposal because she was able to continue on her career path and follow her heart.
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Does Rory cheat on Dean with Jess?

Rory cheated on Dean with Jess

When they finally got together, thanks to Dean breaking up with Rory in front of the entire town, she still couldn't seem to understand why Dean was upset. Eventually, Rory admitted that she still had feelings for Dean.
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Why did Logan Call Rory ace?

Logan's nickname is a cute way to acknowledge Rory's dream career. Gilmore Girls made it clear from the start of the show that Rory's dream was to become a journalist, like Christiane Amanpour. Logan's nickname for Rory is a clever way of him acknowledging her dedication to being an ace reporter.
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Who does Rory sleep with in A Year in the Life?

Then nine years after the original series, Netflix revived Gilmore Girls for A Year in the Life, where Rory and Logan were in the middle of an affair, confirmed in “Winter.” At the time, Logan was engaged to some heiress named Odette.
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Are Rory and Jess endgame?

Fans still can't decide if she should have ended up with Dean (Jared Padalecki), Jess (Milo Ventimiglia), or Logan (Matt Czuchry). And Milo Ventimiglia has his own answer to that question. As it turns out, the Gilmore Girls alum is actually glad Jess and Rory weren't endgame.
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Why Dean was the best for Rory?

1 Dean: He Didn't Bail On Rory When Things Got Tough

Jess, on the other hand, bailed on Rory when things got complicated. He left Stars Hollow and didn't even end their romance properly. This was horrible and showed his immaturity and is one reason why Dean was a much better match for Rory.
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Why Logan is the best Gilmore?

Logan was just as intelligent as Jess

Anyone would sound smart compared to Rory's first boyfriend Dean, but many fans act like Jess was the only boyfriend ever on Rory's level. I'd argue that Logan was intellectually also on Rory's level. Logan challenged Rory constantly and kept her on her toes.
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Does Rory love Jess?

Jess And Rory Officially Start Dating (And Rory And Jess Break Up) Fans love Rory and Dean's Gilmore Girls episodes but once season 3 rolls around, Rory can't hide her romantic feelings for Jess. Dean dumps her very loudly and publicly at the town dance marathon, and Rory and Jess can officially be together.
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Is Jess better than Dean?

His height matches her's much better than Dean's, and he manages to wear the leather jacket without making it look too forced. Jess is also incredibly smart. He matches Rory intellectually and manages to challenge her in ways that Dean never could. Eventually, he even wrote a book!
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Is Jess Rory's Luke?

Of course, Jess' transformation actually began during the original series' run, but it's important to make this distinction now because the revival implied Jess was likely Rory's version of Luke (Scott Patterson) while Logan (Matt Czuchry) was her version of Christopher (David Sutcliffe).
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Who Should Rory end up with?

While Patterson said he has no idea who the baby's father is, he did share his opinion on who Rory should have ended up with on the show: his onscreen nephew, Jess (Milo Ventimiglia).
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Did Rory ever cheat on Logan?

7 Rory Cheated On Paul With Logan

In A Year in the Life, she kept joking around that she had to break up with Paul because she kept forgetting about him. And while she was dating him, she was still routinely sleeping with Logan. Poor Paul didn't deserve to be forgotten.
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