Books
One of the TV shows I most viscerally remember falling for in high school is Gilmore Girls, the show about mom Lorelai and daughter Rory's relationship and adventures. Sure, I watched lots of other stuff, too, of course. But even now I can actually picture myself perfectly, propped up on pillows in my old bedroom, with the massive TV-stand-on-wheels pulled all the way up to the edge of my mattress, so I wouldn't miss a single moment. And yes, the continuing small-town hilarity and complicated mother-daughter relationships were a huge part of the draw. Lorelai, Rory, and Emily Gilmore were the backbone of the series and are the main reasons why my love for the show is so enduring. But I'd be totally lying if I said my teenage self wasn't super tuned in to the romance on the show, too — especially the one between Rory and Jess.
Ah, Jess Mariano. The sarcastic bad-boy with a secret heart of gold, who grew up to become a responsible creative with biceps that just won't quit. I have always been staunchly Team Jess when it comes to Rory's trio of boyfriends (which, for those unaware, include her first love Dean and her college fling Logan) and I will ship them forever. If you're in the same boat as me and you want to read some books with romances that mirror theirs — think bad boy romances, love triangles, second-chance love stories and, of course, bookish couples galore — check out the 13 books below.
'The Unexpected Everything' by Morgan Matson
This rom-com follows Andie, an ambitious teen whose life takes a, well, unexpected turn and Clark, the famous teen author she meets through her dog-walking job. Rory/Jess shippers will obsess over this relationship between a driven high schooler and the bookish guy who helps her see that there's more to life than check-lists.
'By The Book' by Julia Sonneborn
This romance between an English professor and the new president of her college — who just so happens to be her ex-fiancé — has everything a true Rory/Jess shipper needs: A love triangle, a second chance romance, and lots and lots of bookishness.
'One Of Us Is Lying' by Karen McManus
OK, so a mystery-thriller might not be very Gilmore Girls but stick with me, here because there is a romance in the pages of One Of Us Is Lying that just screams Rory/Jess and it will give you all the feels. Seriously, if you're looking for a misunderstood bad boy, a shy bookish gal, and some major sparks flying when the two start to realize their feelings for each other, pick this one up.
'By Your Side' by Kasie West
If you're more a fan of the "wrong side of the tracks" aspect of Rory and Jess's romance, bringing together one teen from a well-to-do family and one from a decidedly different background, you'll love By the Book. Here, Dax (the "troubled" guy) and Autumn get locked in a library together, where they make an unexpected connection.
'The Hating Game' by Sally Thorne
Major Rory/Jess stans will know that the course of their relationship never did run smooth, starting from the fact that there was some major hate-to-love-you vibes at the very start. If that tension was what got you hooked on the couple in the first place, you'll live for the antics between co-workers, and sworn enemies, Lucy Hutton and Joshua Templeman.
'Love, Rosie' by Cecelia Ahern
Two people who are so obviously meant to be together but just can't seem to get right? Love, Rosie is a romance that Team Jess will feel in the depths of their shipping souls. Rosie and Alex seem destined, but so many things get in the way, including school, jobs, distance, and other relationships. This one will get you particularly in your feels if Rory and Jess's relationship in the Gilmore Girls revival made you cry for three days.
'P.S. I Still Love You' by Jenny Han
OK, so you've already read and re-read Jenny Han's To All the Boys I've Loved Before, right? If so, you're going to need the sequel P.S. I Still Love You which places Lara Jean (a kindred spirit to teenaged Rory is ever there was one) in the sort of love triangle that Rory/Jess shippers live for. If you're a fan of the "girl is loved by two handsome, boyfriend-worthy guys whomever will she choose?!" trope, you need this ASAP.
'Anna And The French Kiss' by Stephanie Perkins
You want slow burn romance? You want a love triangle? You want a shy girl, play-it-safe girl falling for an effortlessly cool guy who maybe screws up a lot but is also sweet and smart and gets her out of her comfort zone? Yeah, pick up Anna and the French Kiss without delay. If Etienne St. Clair doesn't give you Jess on his best day vibes, no one will.
'The Education Of Margot Sanchez' by Lilliam Rivera
OK, so Margot Sanchez might be a lot more street smart than sheltered Rory Gilmore, but they actually go through a lot of the same high school experiences. They both attend a prep school where they don't really fit in, they both fall for a "bad boy" with a soft heart who their parents simply don't approve of, and they both have super complicated relationships with their fathers. If you want those same feels, along with some Rory/Jess forbidden romance vibes, pick this one up ASAP.
'How To Love' by Katie Cotugno
You might get some initial Lorelai vibes from this one because, well, teen pregnancy. But Cotugno's book follows sweet Reena and bad boy Sawyer, who fall in messy, complicated love before Sawyer skips town. When he suddenly returns years later, no one wants them together and they both have to decide whether they're meant to be or should let each other go. Which...could they be any more Rory and Jess, or what?
'The Boy Most Likely To' by Huntley Fitzpatrick
When bad boy Tim falls for his best friend's older sister, they both know it's not the best idea. But Tim has never been known for making the smart choice, and Alice is starting to wonder if the “smart” choice is always the right one. This book is about what happens when the charming screw-up and responsible control freak fall in love. Major Rory/Jess feels are about to ensue.
'The Summer I Turned Pretty' by Jenny Han
If small town vibes, complicated family dynamics and the kind of epic love triangle including one sweet, uassuming guy and one "the world is out to get me so I'm going to be a surly as possible even though my heart is secretly on my sleeve" guy is your thing (and, I know it is) get this first book in a trilogy on your shelf ASAP and then marathon read the whole thing before the chilly nights of fall arrive. You won't regret a moment.
'Everything, Everything' by Nicola Yoon
Rory definitely took a risk by dumping her universally beloved boyfriend Dean to follow her heart and date Jess. And Madeline takes an even bigger risk by falling for Olly, who also has a complicated past. If you loved the star-crossed lovers aspect of Rory and Jess's relationship, you'll fall just as intensely in love with the love story in Everything, Everything.
