Once Your Heart Gets Involved, it All Comes Out in Moron: Dating Advice From the Gilmore Girls

Author: Alli Jean, The Dating Game

**Warning: spoilers herein if you haven’t seen Gilmore Girls seasons 1-through-7. If you haven’t, order a pizza, get candy and junk food and coffee and start watching NOW**

It’s fall, so tis the season for apple picking, pumpkin spice lattes…and Gilmore Girls, the iconic WB turned CW dramedy that ran from 2000-2007 and starred Lauren Graham as Lorelai, the flawed, witty and always relatable 32 year old mother of 16 year old Rory, the type-A bookworm with a heart of gold.

Set in fictional Stars Hollow, Connecticut, Rory and Loreai’s stories of steadfast friendship, quirky town traditions, academic pursuits, struggles for acceptance (with their parents and grandparents), and tales of dating, love, and loss resonated with viewers. Although the true #relationshipgoal of this show was to have a relationship with your mom as devoted and realistic as Rory does with Lorelai, that didn’t stop viewers from having fervent opinions about the “Gilmore boys,” who waltzed in and out of the lives of our heroines.

Whether you were Team Dean, Team Jess, Team Logan, Team Luke and/or Team Chris, the Gilmore girls and their various love interests over the years taught us some valuable lessons about dating, loss and love.

Don’t be afraid to say I Love You
For Rory, Dean was the perfect first boyfriend. He was thoughtful, he made her feel special and he respected Lorelai. However, on their three-month anniversary, after a romantic dinner (that yes, involved Rory bringing home a meatball in a reference to Lady and the Tramp), Dean took Rory to show her the car he had been hand-building her, and dropped a bombshell: he said ‘I love you.’


While Rory was flattered and cared about him a lot, she couldn’t reciprocate by saying it back to him, causing him to break up with her. In the midst of allowing herself to wallow, Lorelai told Rory that if she genuinely didn’t feel the same way that’s fine, but after struggling with maintaining relationships for years, she “hoped she didn’t raise a kid who couldn’t say I love you.” Shortly after, Dean shows up at Rory’s private high school and after fighting in front of everyone, Rory finally shouts “I love you, you idiot” (a line, I might imagine many of us have been attempted to use at one time or another).

Despite their fast-paced talking and topical pop culture references, when it comes to relationships and dating, communication is a frequent issue for the Gilmore girls. Early on, Lorelai dates Rory’s English literature teacher, Max Medina, and they eventually get engaged (after he proposes with a thousand yellow daisies, of course). However, Lorelai breaks it off the morning after her bachelorette party, when she realizes she has unresolved feelings for Rory’s father, Christopher, that she has been unable to relay (quick background: when Lorelai got pregnant at 16, Christopher wanted to get married but Lorelai knew they were too young. Christopher has been an absentee father at best ever since but tries to make amends once Rory is in high school).

Speaking of Lorelai and Christopher, things start to heat up for the pair when Christopher starts to regularly visit Stars Hollow. The two finally sleep together the night before Lorelai is due to be the maid of honor in her best friend Sookie’s wedding, when Christopher learns that Sherry, his girlfriend he has just separated from for Lorelai, is pregnant. Since he wasn’t around while Lorelai raised Rory, he doesn’t want to repeat his mistakes and goes back to Sherry. However, neither Lorelai nor Christopher convey how heartbroken they are, which will create unresolved emotions down the line.


Things between Rory and Dean were going well until Luke’s rebellious, literature enthusiast nephew, Jess, arrived in Stars Hollow. Luke’s attempts to turn his nephew’s life on the straight path were fleeting at best, but it was Rory’s intellect and beauty that captivated Jess. Sharing a love of classic and beatnik literature and sense of humor, Jess quickly became the most popular of Rory’s boyfriends among fans.

However, Jess’s teenage angst and tumultuous past made him wary of getting too attached to anyone, even Rory. Jess’s inability to deal with his emotions gets the better of him, he skips out of being her prom date, doesn’t graduate, and takes off to meet his biological father as Rory celebrates being valedictorian at her high school graduation. After she goes to Yale, Jess finally admits how much he loves her and suggests they run away together, but Rory turns him down. Their story isn’t quite finished though, and Jess comes to town on his independent book tour (you wrote a book!) and gives Rory the wakeup call she needs to turn her life around after she has dropped out of Yale. Will the Gilmore Girls revival bring Jess into Rory’s life again? We’ll have to wait and see…

Perhaps there was no bigger struggle to communicate than between Lorelai and Luke, the curmudgeon diner owner who held a torch for Lorelai for eight years, who saw her go from Max to Christopher, to Alex, to Digger (insert collective groan, please). They were a constant source of comfort to each other. Luke was a surrogate father for Rory, he made her coffee cake on her birthday and sobbed at her high school graduation and showed up at the hospital when Lorelai’s father had a heart attack. After dodging questions for years from the gossiping residents of Stars Hollow and Lorelai’s mom, Emily, finally, finally after years of being with the wrong people, Luke and Lorelai made it work…for a while.

In the midst of being in a fight with Rory, Lorelai proposed to Luke, but he couldn’t commit when she wanted to leap forward. Then, through a divisive move from the writers, Luke discovers he has a 12 year old daughter, April, who Luke accepts into his life with open arms while simultaneously keeping Lorelai at a distance. Even a ballad from Fiddler On the Roof couldn’t make Lorelai and Luke communicate what they needed…at least not then. Oy with the poodles!

You Can’t Help Who You Love/It Won’t Necessarily Be the Person Everyone Expects
This message culminates when after her relationship with Luke, a heartbroken Lorelai sleeps with Christopher, dates him, and goes with him to Paris, where they elope. Now, Christopher and Lorelai knew each other since they were teenagers and had Rory, and finally, it seemed as though the timing was right for them to get together. Even after Rory accepted what was happening, Lorelai knew it wasn’t right and tearfully claimed to Chris “you’re the man I want to want.” But he wasn’t.heart

Even though he was Rory’s father and they had so much shared history and they came from the same background, it wasn’t right. Luke was right, it was always Luke. And even though her parents couldn’t necessarily see it and even though it took them over ten years to get together (with a little help from Lorelai singing I Will Always Love You at karaoke night), at the series finale, they finally got their happy ending after Luke worked with the entire town of Stars Hollow to throw Rory a goodbye party before she left Stars Hollow for her first real journalism job.

As Lorelai once proclaimed, “you can’t help who you fall for, Angelina and Billy Bob are a great example of that.” Okay, so they are maybe not the best example but we can only hope that Lorelai and Luke are thriving when we go back to Stars Hollow in a few short weeks.

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