Who did Rory Gilmore cheat on?

Rory cheated on Dean Forrester when she kissed Jess Mariano at Sookie St. James' wedding.
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Why did Rory and Dean split?

From a practical casting perspective, Rory and Dean also had to break up because Padalecki, who played Dean, was cast in the lead role of the new CW series Supernatural. Shooting schedules would not allow him to play both Dean Forester and Sam Winchester, so Rory Gilmore would have to move on to her next great love.
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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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Who did Rory sleep 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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The Downfall of Rory Gilmore



Who does Rory date after Dean?

Dean then broke up with Rory for a second time, after which she started dating Jess. Although Dean and Rory getting back together was never like it was before, the Gilmore Girls season 4 finale saw the two rekindle their romance while Dean was still married to Lindsay Lister.
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Does Rory ever date Tristan?

Together. Never dated. Kissed once, Tristin had feelings for Rory and she was a little interested later on, but never acted on it.
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Does Rory ever date 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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Who does Lane end up with?

Lane married her band-mate Zack in a two-part wedding ceremony.
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Who was the father of Rory's baby?

However, the show does hint as to whom he may be. From a boyfriend to a one-night stand to an illicit affair, A Year in the Life presents a few men who could be possible candidates, but all signs point to Logan being the father of Rory's baby.
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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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Who is the best boyfriend for Rory?

1. Logan Huntzberger

They had not one, but two meet cutes. Logan started off as a complete jerk, but his relationship with Rory makes you love him even more. He was always a great friend (and boyfriend) to her no matter the circumstance. His "Ace" nickname has also gained him points because it's so cute.
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Who married Dean Gilmore?

Dean marries Lindsay in Season 4. While their marriage is a happy one at first, cracks begin to show, and Rory and Dean seem to grow closer. Lindsay tries to be a good wife to Dean, but she is hurt when he begins brushing her aside.
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Why do Jess and Rory break up?

Jess and Rory originally broke up because he just wasn't ready to commit. He was a teenager with a lot of baggage stemming from his abandonment issues, so we'll cut him some slack — but it is hard to defend his leaving town to go find his dad without even giving Rory a heads up.
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Why did Jess leave Rory?

After the wedding, Jess visits Rory at Yale and asks her to run away with him. She declines because she says she no longer wants to be with him by saying "No' repetitively.
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Why doesnt Rory end up with Jess?

Their romantic relationship imploded shortly before the end of season 3, with Jess taking off on a bus bound for California after flunking out of high school. He would later move to Philadelphia and join a small publishing group after an ill-advised attempt to confess his love and win Rory back ended in rejection.
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Who does Rory end up marrying?

Rory doesn't, in the end, marry Logan. But she does get pregnant with his baby, just like Lorelai did with Christopher.
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Who was Rory's first love?

Dean Forrester was Rory's first love. While Gilmore Girls fans liked him during season 1 of the series, his appeal faded rather quickly. By season 2, Dean was a bit whiny and clingy. By season 5, fans detested him after he cheated on his wife, Lindsay Lister, to get back together with Rory.
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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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What episode does Rory find out she's pregnant?

Norman Mailer, I'm Pregnant! is the 6th episode of Season 5 of Gilmore Girls.
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Did Rory and Dean sleep together?

Rory and Dean almost share a kiss when he's working at the Dragonfly Inn, but they are interrupted before it happens. However, on the night of its grand opening, Dean finds Rory collecting CDs at her house, and they end up sleeping together (Rory's first time).
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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 didnt Rory end up with Logan?

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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Why do Logan and Rory break up?

It's in season 6 that Rory and Logan's relationship shows signs of falling apart. After a brief break, Rory learns that Logan slept with other people, and Rory wonders if they can stay together since she has huge dreams for the future and Logan struggles to be responsible and mature.
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