Dean Forester is Rory Gilmore’s first love. Dean and Rory meet in the pilot episode of the series when Rory is packing up her school locker to move from Stars Hollow High School to the prestige Chilton Academy. Rory is struggling to carry all of the things from her locker and drops a few of them on the ground, near where Dean is standing.
Dean gets the nerve to talk to Rory and it’s instant chemistry. The two have a lot of highs and lows throughout the five seasons Dean was on the show. It’s clear that no matter what happens though, Dean will always love Rory. Here are the 10 most romantic things he's ever said over the course of Gilmore Girls.
“I’ve noticed you... Every day.”
At their first meeting, it’s clear that both Rory and Dean are very nervous. They feel something instantly for the other and it’s sweet and innocent and makes us all what it felt like to fall in love for the first time.
Of course, Rory finds a way to start talking about books and Dean asks her how she likes the book “Moby Dick." Rory is surprised that Dean knew what she was reading and when she asks how, he its, he’s been iring her from a distance for a while.
“I just wanted to say that I’m sorry.”
After a couple of flirtatious interactions, Dean starts to wonder if Rory is feeling what he’s feeling. By episode five of the first season, Dean decides he wants to pursue Rory and interacts with her as much as possible, but Rory isn’t as certain as Dean is and is starting to give him the feeling that she isn’t interested.
Dean feels bad for having bugged her and for reading her all wrong, so he goes to her to apologize. He’s vulnerable and his apology is sweet, it also makes Rory realize she is interested in Dean and she tells him that, leaving him with a big smile on his face.
“Don’t worry about it. This is better.”
It’s Rory’s birthday and this year, her birthday falls on a Friday, which means that she will be spending it at her grandmother, Emily’s house, despite Lorelei trying to get Emily to move their standing Friday night dinners to Saturday just the one time.
Instead of cancelling their original birthday plans, Rory gets two parties that year, and Dean isn’t invited to any of them. Rory hasn’t told her mom about Dean yet, but he doesn’t mind. After her second party, Dean surprises her and gives her a bracelet he made.
“I need you not to hate me.”
Lorelei Gilmore is a cool mom, but she can also be a scary mom. Because Lorelei raised Rory all on her own, she’s had to be both good cop and bad cop in Rory’s life. When Rory starts dating Dean, Lorelei’s “bad cop” persona really starts to show.
She invites Dean over to get to know him and while Rory is in the other room, Lorelei gives Dean a list of rules he has to follow in order to continue seeing Rory, which he agrees to, and then he asks Lorelei not to hate him because he knows her opinions mean everything to Rory.
“I am if you want me to be.”
Dean and Rory are still trying to figure out exactly what they are to one another when Rory asks Dean to accompany her to her school dance. Dean isn’t much of a school dance guy, but agrees to go because Rory wants him to.
After the dance and a little bit of drama, Dean and Rory walk through Stars Hollow and Rory decides to ask Dean if he’s her boyfriend. After a few minutes of banter and deflection, Dean finally tells Rory that if she wants him to be her boyfriend, then that’s what he is.
“Rory, I love you.”
On Dean and Rory’s three months anniversary, Dean plans the perfect night for the happy couple. He takes Rory to a nice dinner, they split a delicious tiramisu, they go to the Stars Hollow annual bonfire, and then he takes Rory to a junk yard, which at first, seems a little strange, until he shows Rory the car he’s been building for her.
The two lovebirds cozy up in the car that will someday be Rory’s, once it’s up and running, and Rory notes how perfect the night has been. Dean responds by telling Rory that he’s in love with her.
“Me? I’m an idiot.”
Rory and Dean have their fair share of fights throughout their relationship. One of their earlier fights is when Rory starts to panic about not having enough extra curricular activities to get into Harvard. She tries to cancel plans with Dean so she can start planning how to build her resume for her college applications and that makes Dean pretty unhappy and somewhat jealous.
After their fight, Dean finds Rory to apologize, takin full responsibility and adding in a little self-deprecation to show Rory how sorry he is.
Dean Comes To Chilton
Sometimes, Dean doesn’t need words to tell Rory exactly how he feels. Rory and Dean break up after Dean says “I love you” and Rory can’t say it back because she isn’t ready. They’re both heartbroken and it’s clear neither wants to be apart.
Rory tries going by the market where Dean works, she grills Lane for information, she even shows up at Dean’s house, but she’s at a loss. Dean doesn’t say much, but when he shows up at Rory’s school to see her, Rory knows that he still loves her and she finally gets the nerve to say it back.
“Actually, it’s not bad at all.”
Stars Hollow annual twenty-four hour dance marathon has come around again and Lorelei is particularly excited for the event. She convinces Rory to be her dance partner, drags her out of bed at a very early hour, makes her dress up in 40’s style clothing and dance until she is physically exhausted.
Rory and Dean’s relationship has been rocky up to this point because of newcomer, Jess, but right before Dean and Rory break up, they share a sweet moment on the dance floor where Dean steps in as Rory’s dance partner and he gets to her hold her one more time.
“I can...”
Dean and Rory can’t seem to stay away from each other, even once Dean is married to another woman. Dean has been married to Lindsey for about a year, when he and Rory cross paths again. Dean tells Rory his marriage is failing and that they aren’t happy together.
Rory tells Dean she’s sorry to hear that because she wants him to be happy and he responds by telling her he will be happy again someday, “everything happens for a reason," he says to Rory right before he kisses her. She can’t believe they’re back together, but Dean confidently tells her he can believe it.