As one of the hit teen drama series of the early 2000s, The WB/CW series Gilmore Girls truly played a key role in defining the shipping culture that we know today. While most people spent their shipping energy debating the merits of Rory Gilmore's main trio of love interests, there's another list of potential relationships well worth debating when it comes to the series' other protagonist, Lorelai Gilmore.
Lorelai has her fair share of relationships during the series' original seven season run, but there are also plenty of other romantic options the series didn't pursue, but could have. Though Lorelai was clearly meant to end up with grumpy diner owner Luke Danes, here are ten other characters from Gilmore Girls she could have been with instead.
Jackson Belleville
It might be hard to picture, but in a world where hippie produce farmer Jackson Belleville didn't fall in love with Sookie St. James, he would have made quite the amusing significant other for Lorelai herself.
Jackson's high strung, neurotic, environmentalist ways would have provided a great balance to Lorelai's Type A, bold, junk food loving personality. Maybe these two wouldn't have worked out in the long run, but they would have made for some great comedy all the same.
Jason "Digger" Stiles
In a version of the series where Jason "Digger" Stiles didn't get involved in business with Richard Gilmore, and later attempt to sue him, it's entirely plausible to imagine his relationship with Lorelai continuing.
Not that we would have necessarily been on board with it, because Digger is the worst, and the chemistry was never quite there. But these two have shared history, and a certain kind of snarky spark that tends to flourish in the world of Gilmore Girls.
Finn
We might be verging into some Mrs. Robinson territory with this one, but there's no denying that Logan Huntzberger's fellow playboy friend Finn absolutely had the hots for Rory's mother on the brief occasions the two interacted.
Lorelai may have been a bit older than Finn, but something tells us that Finn of all people definitely wouldn't mind that fact. Whether Lorelai would charmed by his childish yet suave ways remains to be seen, but it sure is funny to think about.
Christopher Hayden
This one is also tough to think about, but there's no way of avoiding its inclusion on this list. Given the polarizing original final season of Gilmore Girls, there was once a world in which the relationship between Lorelai and high school sweetheart Christopher Hayden could also have been the series' endgame.
Time and again, these two proved why they were terrible for one another. But time and again, they kept finding their way back to each other, even impulsively getting married. Had it not been for the final few episodes of the series, they could have stayed that way.
Paul
Finn isn't the only younger guy who could have maybe gotten Lorelai's attention. One brief relationship Lorelai has during the original run of the series does, in fact, find her dating a much younger guy, even though she's initially unaware of the age gap.
During her night business school classes, Lorelai hits it off with a fellow student named Paul, who's charming and cute and sweet, but also happens to be actually college-aged and therefore well out of Lorelai's dating comfort zone. Had that not been the case, these two would have been cute together.
Kirk Gleason
Don't laugh. There was once a time where Kirk Gleason was clearly crushing hard on Lorelai Gilmore, and who could blame him? Though he may be one of Stars Hollow's weirdest residents, there's no denying that Kirk is also one of its most reliable.
And he also happens to be there time and again for Lorelai all throughout the series, even though its often in his own quirky, unexpected ways. A relationship between these two might seem wildly unrealistic, but it's still fun to think about all the same.
Peyton Sanders
When Jon Hamm guest starred on Gilmore Girls as a son of one of Emily Gilmore's friends, he was still an unknown in the world of pop culture. But he certainly left an impression on Lorelai in his role as Peyton Sanders, a man Lorelai immediately deemed too dull to date.
Had that not been the case, or had Lorelai given their relationship more time to develop beyond a single date, the on screen presence of Lauren Graham and Jon Hamm alone would have been more than enough to make this a relationship worth rooting for.
Sookie St. James
Few friendships in the entire series are more devoted, more reliable, and more all enduring than the one between best friends and business partners Lorelai Gilmore and Sookie St. James. Is it really such a stretch, then, to imagine a world in which these two became the will they, won't they couple everyone was rooting for?
Gilmore Girls, as a product of the early 2000s, wasn't particularly known for its LGBTQ representation. But had it been, these two would have been a great example.
Alex Lesman
Lorelai only has a handful of real relationships over the course of the series, but the one that receives the least attention and least explanation for its ending also just so happens to be one of her best.
Her short-lived relationship with Alex Lesman, portrayed by Billy Burke, introduces a side of Lorelai we don't see often: a Lorelai who's willing to try new things. Plus, their bond over coffee and the natural ease and chemistry in each of their scenes made their relationship a treat to watch, no matter how brief it may have been.
Max Medina
But if there was one character that Lorelai truly could have had it all with, it was Scott Cohen's Max Medina. These two had everything from the beginning: a shared sense of humor, the element of opposites attracting, a genuine interest in all aspects of each other's lives, and a truly incredible chemistry few other couples on the series could match.
If it weren't for the out of nowhere and hard to believe claim that Lorelai didn't love Max after all, these two very likely would have gotten married. And we'd be lying if we tried to claim we don't often wonder what that series would have looked like.