Gilmore Girls: 10 Episodes That Prove Rory & Dean Were Soulmates

One of the things that made Gilmore Girls great was being able to watch the characters grow up, meet new people, and fall in love. This was especially true for Rory Gilmore, given that she started the show as a teenager. Dean was the first guy that fans got to see Rory fall for and many thought they would be endgame.

Despite fans’ hopes, the show did keep some realism to it, and we saw them go through multiple breakups and the two of them finding love with other people. Even if Rory and Dean didn’t end up together in the show, there are many scenes that prove the two were meant to be soulmates.

10 Kiss and Tell (S1, E7)

Out of all of Rory’s boyfriends, Dean was the only one who regularly joined in on her and her mom’s movie nights. This episode is the first time we get a taste of that, and it was their very first date together. It was when Lorelei finally accepted Dean and it started the trend of him regularly going over.

This episode showed the extend Dean was willing to go to be with Rory, even if her family wasn’t fond of him. He also attended Friday night dinners with her grandparents, even though they often made him feel out of place.

9 Rory’s Dance (S1, E9)

Early in season 1, Dean attended a dance at Chilton with Rory, which resulted in the two having so much fun that they fell asleep at Miss Patty’s dance school. After this, Lorelei was so upset with Rory after she suspected more might have happened between them.

In reality, this was an incredibly sweet and innocent moment between the two. Dean was with Rory for a long time, but he never pressured her to move too fast or do anything more than a kiss.

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8 Star-Crossed Lovers And Other Strangers (S1, E16)

In this episode, Rory goes on one of the most romantic dates that she had in the whole show. Dean takes her out for dinner, then they spent the night out together in a car looking up at the stars and he tells her he loves her for the first time.

It’s one of the most memorable episodes, especially because it’s also when Rory goes through her very first breakup. As sad as the ending of this episode is, it’s hard not to acknowledge how much effort Dean always went through to make Rory happy.

7 Double Date (S1, E12)

Dean is the only one of Rory’s boyfriends that hung out with her friends, especially Lane. Jess and Lane didn’t even get along, in fact, Lane didn’t even like Jess. Logan, on the other hand, was always polite but distant. He wasn’t able to bond with Rory’s family and friends the way Dean did.

In this episode, Dean helps Rory set up Lane with a friend of Dean’s, and the group goes on a double date together. It’s not the only time we see Dean spending time with Rory’s friends, and he’s the only boyfriend of hers who ever did.

6 Richard In Star’s Hollow (S2, E12)

In season 1, Dean spent a lot of time building Rory a car and revealed the news to her on her anniversary. That wasn’t the only pivotal gift that Dean presented to Rory, he also made her a bracelet that she never took off. It was obvious that Dean put a lot of effort into his gifts for her.

In season 2, he finally gave her the car that he has spent so much time working on for her. Richard opposes Rory driving the car, but after multiple inspections, he lets Rory accept Dean’s gift.

5 Love, Daisies, and Troubadours (S1, E21)

After Dean told Rory that he loved her for the first time in season 1, Rory became uncertain about her feelings and couldn’t find the words to reply, ruining what was supposed to be a special day for the two.

This incident resulted in Rory’s very first break up, but her time apart from Dean just made her realize how strong she truly felt for him. Rory went through a huge slump without Dean and later reveals to him that she actually does love him.

4 Face-Off (S3, E5)

When Rory realizes that Dean is in a new relationship at his Hockey game, she doesn’t handle the news well. She even confides in Lane that she wished Dean would have tried harder to get back with her.

Even though he was in a new relationship, it’s clear that their feelings for each other were always mutual, even if they couldn’t admit it to each other. Later in the episode, Dean gets into a fight with Jess after he made Rory cry, proving once again that Dean will always care for Rory.

3 The Big One (S3, E16)

Early in Dean and Rory’s relationship, Dean wasn’t sure if he wanted to attend college. Unlike Rory, in which going to Harvard was a huge priority, it wasn’t of much importance to Dean. After his break up with her, it’s obvious that Rory was actually an influence on him since he ended up getting accepted to college after all.

In this episode, Rory gets accepted into Harvard and Dean reveals to her that he was also accepted. Of course, the two were super proud of each other.

2 Raincoats And Recipes (S4, E22)

Dean and Rory’s affair is a bit controversial, but it was a huge moment in both of their lives. This was the first time that Rory ever slept with someone. She previously had the opportunity to have her first time with Jess, but she rejected him.

The fact that she wanted to share that experience with Dean shows how much he meant to her. Even though Dean was married at the time, this was the moment that made him rethink his marriage and realize he will always love Rory.

1 Fall (A Year In The Life)

When fans finally got to see Rory and Dean reunite in Gilmore Girls: A Year In The Life, the two had a heartwarming discussion about how they were both so important in each other’s lives.

She acknowledged that he was the perfect boyfriend to her and an integral part of her growing experience. Rory even admitted that had they met later in life, they might have actually had a successful relationship, and she wished it could have been that way.

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