Airing from 2000 to 2007 on The WB and The CW, and with a revival miniseries released on Netflix in November 2016, Gilmore Girls wasn’t just your average teenage drama. As a multi-generational story, the world of Gilmore Girls was packed to the brim with characters, and characters looking for love in the wrong and right places as well. Leading ladies Rory and Lorelai had their fair share of failed relationships, most of which fans have come to have incredibly passionate feelings about in time.
But no matter which team you may subscribe to, or which storylines you were pleased or dissatisfied with, it’s clear that not all of the romantic relationships within the world of Stars Hollow were given the same quality of development and writing. Some relationships served the series and its characters much better than others, while some relationships only hindered growth and reduced the series’ overall quality. We rank the best and worst couples in the show below.
Best: Zack and Lane
From day one, it was clear that Lane Kim had aspirations for a life larger than what Stars Hollow could offer her. A true rocker in her soul, Lane wasted no time in trying to find likeminded musical individuals. And though it took some time, she eventually found her other half and perfect match in her eventual bandmate, the awkward ladies’ man Zack Van Gerbig.
It took these two a bit of time to finally sort out their feelings and issues and make it work, but as soon as they got together, they made sweet music together, both figuratively and literally. The show may have taken a real misstep with these two in its final season, by making Lane wind up pregnant with twins immediately after they finally got married. But at the end of the day, these two are soulmates, in music and in life.
Worst: Rory and Paul
Oh, Paul. Poor forgotten Paul. For some reason in the revival miniseries Gilmore Girls: A Year In The Life, the decision was made to give Rory a perfectly nice and boring boyfriend named Paul that she would quite literally forget existed, at the drop of a hat. As if that was something people actually do. Making matters worse, Lorelai never seemed to remember that Paul ever even existed either.
We’re sure Paul is a perfectly nice guy, which makes Rory’s selfish and cruel behavior all the more disturbing. And that’s all before even taking into account the multiple occasions in which Rory cheats on him. Thankfully, Paul breaks up with Rory at the revival’s end. He deserves better - and someone who will actually remember he exists.
Best: Lorelai and Max
It’s practically unheard of for a character in any drama series to wind up with their first love interest. But if Lorelai Gilmore and Max Medina had wound up together in the end, would that really have been so bad? From the moment Lauren Graham and Scott Cohen shared the screen, the chemistry was undeniable, no matter the awkward scenario of Max being Lorelai’s daughter’s teacher.
Max and Lorelai both educated each other about different aspects of life that neither one of them knew very much about. Max also cared deeply about Rory, and would have been a wonderful father to her, something they both even discuss. The way the series handles the dissolution of Max and Lorelai’s relationship and engagement is still unsatisfying after all these years, because these two really could have made it work.
Worst: Rory and Dean
First loves are formative experiences that can really do a lot in terms of shaping who people will eventually become. Unfortunately for both Rory and Dean, their first love made them both ugly, selfish, careless people. In the early days of their relationship, they were sweet and harmless enough. But over time, Dean began to show his ugly jealous side, while Rory showed her first signs of being willing to cheat on someone, no matter how it might hurt them.
They would break up and get back together a few times during their primary relationship. It even seemed like things would be over for real this time when Dean married Lindsay, another student at Stars Hollow High. But of course not. Rory and Dean engaged in an affair, publicly ruining lives and humiliating themselves in the process, before attempting an abbreviated, uncomfortable relationship yet again.
Best: Rory and Jess
Opposites certainly do attract in the world of Gilmore Girls, but sometimes, there’s no denying a connection found with someone you share all the important things with. From the moment he set foot in Stars Hollow, Luke’s nephew, Jess Mariano, was guaranteed to shake things up. Jess immediately sparked with resident good girl Rory, and the two would go on to share books and notes and engage in secret meetings, despite Rory’s boyfriend’s misgivings.
In the end, these two couldn’t deny their feelings for each other. Unfortunately, the show seemed to give up on their relationship long before it actually ended, leading to multiple out of character decisions on both character’s parts. By the end of the series, and the revival as well, Jess had matured and grown the most out of Rory’s love interests, proving that he might just be Mr. Right for her after all, if she ever opens her eyes to that possibility again.
Worst: Lorelai and Jason
Gilmore Girls never shied away from putting two people in relationships after they got off to a rocky start. Take, for example, the terrible choice to put Lorelai in a relationship with Jason “Digger” Stiles, a petulant man child she’d once attended summer camp with and been tormented by during their years of puberty.
Jason and Lorelai had absolutely nothing in common when they were teens, other than an attitude problem, and that same lack of similarity persisted into adulthood. Add in a total lack of chemistry between actors, and Jason’s complete betrayal of onetime business partner Richard Gilmore, and this relationship was nothing more than a hot mess.
Best: Richard and Emily
Whether you loved them and their world of glitz and glamour, or felt irritated by the lifestyle they represented, there’s no possible way of denying that the love between Richard and Emily was one of the series’ most reliable and strongest plot points. Whenever these two were on the outs with each other, nothing felt right in the series’ universe. They were true partners, in love and life and so much more.
They even received the honor of having their wedding vow renewal serve as the series’ landmark hundredth episode, which just signifies the strength and significance of their relationship. Following Edward Herrmann’s tragic passing, Emily is entirely lost as to what her life should be now in the revival. In time, she figures things out; but Richard’s absence and the legacy of their love looms large.
Worst: Rory and Logan
The central conflict at the heart of Gilmore Girls, beyond the generational family feud, was the push and pull between the upper and lower class structures that the Gilmore family inhabited. Richard and Emily represented the wealth that Lorelai deliberately raised Rory away from. But in the end, Rory found herself drifting away from the hardworking life, taking up with the human embodiment of privilege in Logan Huntzberger.
From day one, these two brought out the worst in each other, and it only became apparent over time. From repeated instances of cheating and public humiliation, to encouraging Rory to steal a yacht and drop out of Yale, and all the way to the disappointing affair storyline in the revival series, Logan made Rory an almost completely unlikable person.
Best: Lorelai and Luke
Rory’s romantic options may have taken up most of the discussion in the world of Gilmore Girls relationships, but here’s the real truth: the love story most worth rooting for in the series was the one between a grumpy diner owner and a coffee addicted single mom. From day one, Luke and Lorelai understood each other in ways no one else could.
They might not have been an intentional relationship, but sometimes, you just can’t fight chemistry that naturally develops. While these two took their sweet time getting together, and were ultimately derailed in the series’ final two broadcast seasons by some poor writing decisions, Luke and Lorelai’s relationship is one of the strongest parts of the series, and has stood the test of time as one of the best love stories in the modern era of television.
Worst: Lorelai and Christopher
As we’ve previously explored, just because people are each other’s first loves, that doesn’t mean that they should be together forever. Nor does having a child together make two people each other’s soulmates. The totally toxic relationship between Lorelai and Christopher is a perfect encapsulation of both of those facts.
Despite their past as high school sweethearts, Lorelai and Christopher routinely proved that they were completely wrong for each other again and again. Christopher was never reliable, often stringing Lorelai along with promises of a life he would never actually commit to - at least not with her. When the series’ polarizing final season on The CW had these two briefly get married, the show had well and truly finally jumped the shark.
