For many Gilmore Girls fans, Logan Huntzberger is charming and Jess Mariano is an intriguing rebel, but Dean Forester is a perfect first boyfriend for Rory Gilmore. Dean is sweet, appreciates small-town living, and isn't even intimidated by Rory and Lorelai's super close bond. Fans love watching Dean and Rory meet and begin their relationship, and the ups and downs of their love story makes for great dramatic TV.

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While Dean has some flaws and many viewers don't think he's right for Rory in the long run, he's a significant part of Gilmore Girls, and he has many compelling storylines that stand out to viewers.

Dean's A Good Sport About Movie Night

Lorelai, Rory, and Dean eating pizza at home on Gilmore Girls

While season 1 has sad and funny scenes, it also features the episode "Kiss And Tell," which is a favorite for many fans. Lorelai asks Dean to come over and have some pizza, junk food, and watch Willy Wonka And The Chocolate Factory, he agrees, even though he feels a bit awkward at first.

Not every high schooler would want to have dinner and watch a movie with their crush's parent, but Dean is game, and this is one of his most endearing moments. Fans love this storyline because Dean proves that he likes Rory and Lorelai's relationship. It's clear that he will never say a negative word about it, which is important.

Dean Shows Lorelai That He's Good For Rory

Lorelai talks to Dean outside of Dooseys Market on Gilmore Girls

After Dean and Rory are found sleeping in Miss Patty's dance studio, it's no wonder that Lorelai and Emily are angry, as they have flashbacks of Lorelai's high school pregnancy. In the next season 1 episode, "Forgiveness and Stuff," Lorelai and Dean have a conversation that is both tricky and dramatic.

When Dean tells Lorelai "She will go to Harvard and if she doesn’t it won’t be because of me," she realizes that he's a good person and that he would never stand in the way of Rory's bright future. This is a huge moment for Dean, as he's strong and confident but still kind and respectful.

He And Rory Fight Over His Love Of Donna Reed

Rory dressed up like Donna Reed standing on a front porch behind Dean on Gilmore Girls

In what is one of the most famous early episodes of this beloved show, Dean shares with Rory that he thinks Donna Reed is great. He loves thinking about a wife and mother making dinner for her family, and he thinks it's cozy, sweet, and comfortable.

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Viewers like this plot because it shows how different Rory and Dean are and also sets up how they might not be right for each other as they get older. Dean dreams of a domestic family scene, and Rory is more focused on her career.

Dean Is Devastated When Rory Can't Say She Loves Him

Split image of Dean and Rory in the car he bought her on Gilmore Girls

The season 1 episode "Star-Crossed Lovers and Other Strangers" definitely breaks fans' hearts every time they watch it again. Dean tells Rory he loves her after three months of dating, and it's too scary for her to say it back.

There are many Gilmore Girls episodes about Dean and Rory that viewers love, and this one is up there. While it's so sad to think about Rory and Dean breaking up, this is one of his best storylines because he takes a risk and puts it all out there. He doesn't want to wait to share how he feels, and this is a good lesson for both him and Rory, even if their love story takes a sad turn.

Dean Worries About Rory Going Off To College

Rory and Dean talking in Rory's kitchen on Gilmore Girls

In season 2, Dean realizes that it's time to face facts: college is fast approaching and Rory is dreaming of going to Harvard. Even if they date long-distance, he doesn't think that she has enough time for him in the present, and he thinks that might led to problems later on.

While this Gilmore Girls relationship is sweet and innocent in many ways, it also has many dramatic moments, making this one of Dean's most memorable storylines. Dean loves Rory but knows that he deserves someone who he has a real future with.

Dean And Tristan Fight Over Rory

Split image of Tristan, Rory, Paris, and Dean at a play rehearsal and Tristan and Rory rehearsing on Gilmore Girls

The season 2 episode "Run Away, Little Boy" sees Rory and Tristan playing Romeo and Juliet, which gives Tristan the opportunity to tease Dean when he comes to a rehearsal. When Dean and Tristan fight over Rory, it's an intense echo of the conflict they had at the Chilton dance earlier on in the show.

Fans can see that Rory likes both Tristan and Dean, and Rory is scared here because she doesn't want Dean to learn that she and Tristan kissed at a party after their break up. For many viewers, this is a significant moment for Dean as he seems too jealous of Tristan and he needs to trust Rory more.

Dean Breaks Up With Rory Because Of Jess

Split image of Rory and Dean dancing at the marathon on Gilmore Girls

It's a shock when Dean breaks up with Rory at the Stars Hollow dance-a-thon, but viewers know that the sparks flying between Rory and Jess are impossible for him to ignore.

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This is one of Dean's most important storylines as he feels embarrassed that his partner has been flirting with someone else. He doesn't want to stand back and watch it happen anymore, and he knows that it's time to let Rory go, even though it's painful.

Dean Marries Lindsay But Is Unhappy

Lindsay and Dean kissing in the Dragonfly Inn on Gilmore Girls

It's pretty shocking when Dean shares that he's engaged to Lindsay, especially since his feelings for Rory have always been so strong. But if a character on the show was going to get married young, it would definitely be Dean.

While Lindsay and Dean don't stay together, their marriage is a big part of Gilmore Girls. Dean learns an important lesson: while he wants marriage and a family, he can't settle, and he has to look for a partner who truly cares about him.

Dean And Rory Begin Dating Again, But Something Is Off

Rory and Dean in bed in Gilmore Girls

When examining the mistakes and choices that Rory has made, most fans would say she shouldn't sleep with Dean when he's married. The decision that the former couple makes at the end of season 4 leads them to get back together in season 5.

It's realistic and true to life that when Dean and Rory try their relationship again, they know something is missing. Dean is out in the world working and Rory is studying at Yale, and they don't have the bond that they once did. They also don't seem to have much in common now. Fans respect that Dean can accept the situation and move on from Rory.

Rory Thanks Dean In The Revival

Dean and Rory talking at Doose's Market on Gilmore Girls: A Year In The Life

In a moving scene, Rory sees Dean at Doose's Market in A Year In The Life, and she says thank you for being a wonderful first boyfriend. She says he made her feel safe and she knows this was a really big deal.

Dean's final storyline has a lot of significance, as he is glad to hear Rory's kind words and appreciation, but he doesn't need to hear these words as much as she needs to say them. Dean is married and has the family he wanted, and he can look back on Stars Hollow and his teenage years fondly, but he is grown up and at peace.

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