Books
When it comes to Gilmore Girls, the "ships" are many and complicated. Both Lorelai and Rory meet various men, with varying levels of emotional intelligence and relationship readiness, as they flit in and out of their lives. There is, of course, the ultimate question of whether Lorelai and Christopher, her high school sweetheart and father of her only child, or Lorelai and Luke, the diner owner who has carried a flame for her since the moment they met, are truly meant to be. And then there is Rory, whose three boyfriends — Dean, Jess, and Logan — have caused major divides in the fandom.
While very strong arguments can be made both for and against each of these men, almost 20 years after the show's premiere, it's Dean Forester who remains perhaps the most controversial. Devoted viewers — staunch Team Jess or Team Logan members, especially — will remember Dean as undeniably possessive, jealous, suspicious, and, ultimately, unfaithful in his obsessive pursuit to win back Rory's affections (after she had already dumped him.) But to focus only on those attributes would be to erase other truths: Dean was Rory's first love. He was the guy that changed the hot water bottle, the guy who accompanied Rory on hours-long bookshop crawls, the guy who was predictable, steady, and safe.
I think, to truly understand the Rory and Dean shipper is to understand the nostalgia that comes with earnest and un-jaded first love, and the hopeful beginning of any new relationship. Below are 11 books about first loves, new romance, and second chances with the ones who got away:
'I Believe in a Thing Called Love' by Maurene Goo
Rory Gilmore and Desi Lee have a lot in common: both are super-smart overachievers who don't have any dating experience. And like Rory, when Desi meets the new guy at school, she decides to dive into a relationship for the first time. But not without first making a list: the K-Drama Steps to True Love, which she hopes will help her find true love.
'Foolish Hearts' by Emma Mills
When Claudia is forced to perform in the school play with her enemy, her senior year suddenly becomes... life-changing. A wholesome romance between Claudia and the goofy but handsome Gideon, mashed together with the small-town high school vibes and complex family relationships, makes Foolish Hearts as cozy as any season one Gilmore Girls rerun.
'Twice in a Blue Moon' by Christina Lauren (Oct. 22)
When Sam Brandis and Tate Jones meet on vacation in London, they embark on a whirlwind romance that ends in a shocking betrayal — until they unexpectedly meet again 14 years later. Sheltered small-town girl Tate and earthy Sam will definitely give you Rory and Dean vibes, as will their second-chance romance.
'To All the Boys I've Loved Before' by Jenny Han
Like Rory, Lara Jean is a now-iconic example of a girl who is more used to living in books and daydreams than in real life. But when Lara Jean's secret love letters accidentally get sent out, she teams up with Peter, one of the letter recipients, to deal with the aftermath.
'Small Town Hearts' by Lillie Vale
There's coffee and pie on the cover, so we know this book already has a couple things in common with Gilmore Girls. Babe Vogel just graduated and has the whole summer in her sleepy Maine beach town before her. But when Babe falls for Levi Keller, a new guy in town for the next few months, her plans are upended.
'Say You Still Love Me' by K.A. Tucker
Piper Calloway is super successful, lives in a swanky townhouse and has two best friends she adores. But her romantic life is less than stellar. And when her first love, Kyle Miller, is hired as the security guard at her work, things get more complicated. This is a second chance romance that has Rory and Dean, season five, written all over it.
'Hello, Goodbye, and Everything in Between' by Jennifer E. Smith
Before Rory fell for Jess's bad boy charm, it looked like she and Dean were in it for the long haul. But they were both worried about what would happen when Rory went off to the Ivy Leagues and Dean stayed in Stars Hollow. In Jennifer E. Smith's book, high school sweethearts Clare and Aidan grapple with the same issue on the last night of the summer.
'When Dimple Met Rishi' by Sandhya Menon
Dimple is a smarty-pants gal who is more interested in school than boys. Rishi is a hopeless romantic who believes he and Dimple are meant to be. Both Dimple and Rory are tempted into first time love by super sweet guys who are definitely the types to say "I love you" first.
''Don't You Forget About Me' by Mhairi McFarlane
Think of Don't You Forget About Me as what would have happened if Rory and Dean reunited in the Gilmore Girls revival rather than in the latter half of the original series. Georgina (like revival Rory) is totally lost in her career and her personal life. When she unexpectedly meets Lucas, her first love, everything changes.
'The Sun Is Also A Star' by Nicola Yoon
If that exciting, all-encompassing emotion of first love is the real reason you still ship Rory and Dean, you're definitely going to love The Sun is Also a Star. This book — which follows Natasha and Daniel as they fall in love on a whirlwind day in New York City — is about as earnest as it gets, full of the kind of romance you can only have when you're young.
'Second Chance Summer' by Morgan Matson
When Taylor Edwards and her family return to their house in the Pocono mountains under tragic circumstances, Taylor reunites with her first boyfriend. Small-town charm mixes with first love, family dynamics, and ruminations on life and second chances — and it's perfect for fans of Gilmore Girls and, of course, its inaugural teen couple.
