Gilmore Girls has long been beloved for its portrayal of complex family relationships, especially those between parents and their children. The cult hit series, which ran for seven seasons from 2000-2007 on The WB and The CW, as well as a limited series revival on Netflix in 2016, is renowned for its honest discussions of difficult issues facing women and families, its signature joke-per-second brand of humor, and its all-encompassing grasp on popular culture.
Lorelai and Rory Gilmore set high expectations for a generation of television viewers, not only in terms of the relationship they had with each other, but also in terms of the romantic relationships they had over the course of the series. While Rory's relationships may have been more hotly contested, featuring passionate fans on various teams, such as Team Jess or Team Dean, Lorelai had her fair share of relationships, too.
Some of Lorelai's relationships were much better than others, however - and though she would eventually wind up with lovable curmudgeon and diner owner, Luke Danes, it's long been debated whether he's the best of all her love interests. We offer our take on the debate below.
Boyfriends don't get much worse than Rune Belleville. Honestly, Gilmore Girls characters don't get much worse than Rune Belleville. When Jackson's cousin Rune comes to visit Stars Hollow, it just so happens to coincide with when Jackson and Sookie are planning to go out on a date. So, in order to keep his obnoxious cousin occupied, poor Lorelai gets roped into a double date.
Rune never has a single pleasant thing to say, complaining about everything about the evening, and about Lorelai herself - who is, without question, extremely far out of his league. But to Rune, dating Lorelai is unthinkable. Thankfully, it never happens again.
7 Jason "Digger" Stiles
Having a shared history doesn't exactly mean that you're going to be a good fit as a couple in the future - especially when that history took place when you were dumb, hormonal teenagers. Lorelai and Jason "Digger" Stiles met at a summer camp when they were younger, and took part in a very childish, pigtail pulling sort of flirtation that involved Jason publicly humiliating Lorelai by soaking her t-shirt.
Fast forward twenty years later, and their mutually snarky brands of humor somehow lent themselves to a relationship that never should have happened in the first place. From the moment they shared the screen, these two just didn't fit. And that, of course, was long before Jason betrayed his own business partner - who just so happens to be Lorelai's father, Richard.
6 Christopher Hayden
Speaking of teenage histories not exactly translating well into present-day relationships, have you met Christopher Hayden? As Rory's biological father, Christopher is about as unreliable as they get - until he wants something, conveniently. He drops in and out of Rory and Lorelai's lives, leading Lorelai on time and again even when he's currently in a relationship. They banter, they reminisce, they inevitably kiss or sleep together at the wrong time.
It's a tired pattern the show uses and abuses far too often - a pattern that's stretched to the point of ludicrousness in the show's widely maligned final season, which finds Lorelai and Christopher eloping on a vacation to Paris. First of all, the thought that Lorelai would get married without Rory present is an insult all on its own. But furthermore, the fact that these two would ever be marriage material - after all they went through - may be the biggest joke in the ever witty series.
5 Peyton Sanders
From the very beginning of the series, one thing is clear about Lorelai Gilmore: she does not want to be part of her parents' world - and yet, she finds herself drawn back into it over and over again. One of the most surprising examples of that comes in the third season when, attending an auction, Lorelai hits it off with a mystery man. Jon Hamm's Peyton Sanders turns out to be the son of some of Emily and Richard's ultra-elite friends.
Cue Lorelai's horror when she finds herself retreating to her parents with her tail between her legs, seeking their help arranging a date between them. But, of course, Lorelai being Lorelai, her opinion of Peyton is soured from then on - and only compounded further by how utterly boring she finds him to be. Peyton is never seen again after that.
One of Lorelai's best storylines takes place in the series' first couple seasons, when she attends night classes for business school in order to prepare herself for opening her dream inn one day. During the second season episode "Run Away, Little Boy," Lorelai has a sweet, cute flirtation with a fellow business school classmate named Paul, portrayed by eventual Pretty Little Liars recurring star Bryce Johnson.
It seems like there's a promising future for these two - until Paul arrives at Luke's Diner a few days later, looking especially boyish, and accompanied by his parents, who can't be more than 10-15 years older than Lorelai at the time. It suffices to say there's no future for their relationship as soon as Lorelai realizes just how young he is - but that certainly doesn't stop Luke from having a field day with it.
3 Alex Lesman
One of Lorelai's best boyfriends - who inexplicably, and disappointingly, disappears without a trace - is undeniably Billy Burke's Alex Lesman. Alex is another boyfriend that Lorelai meets thanks to Sookie, since he is working with one of Sookie's former friends. When Lorelai and Alex met, there's immediately a spark - one that only grows when it turns out that the first date he asks Lorelai out on winds up being a coffee tasting adventure.
And if there's a direct way to Lorelai's heart, coffee is most certainly it. Alex is around for a few episodes in the third season, including one that finds Lorelai stepping out of her comfort zone and learning how to fish so she can accompany him on a fishing trip. They remain together for most of the third season - or at least we're told so - but then, without a word, they're no longer together.
2 Luke Danes
From the pilot episode, it was instantly clear that Gilmore Girls truly had something special in the relationship between the ever perky and caffeinated Lorelai Gilmore and the lovably grumpy diner owner Luke Danes - especially considering Luke's character was never meant to exist in the first place. For the first four seasons, the series plays the "will they, won't they" game with these two - and does so incredibly well.
Despite many other relationships and roadblocks along the way, these two find their way to each other time and again. They understand each other, and they support each other, even when they're at their worst. And though they may not always be the best at communicating clearly, it's clear that these two are made for each other. After all, who else would make Lorelai all the coffee she needs?
1 Max Medina
Luke Danes may be Lorelai's soulmate, but that doesn't necessarily make him the best boyfriend she's ever had. That distinction instead belongs to Max Medina, Lorelai's boyfriend and eventual fiance - who also happens to be Rory's English teacher at Chilton. Out of all the men that Lorelai dates, Max is the best of them all. He's kind, smart, sensitive, and always willing to do whatever Lorelai and Rory need him to do.
He loves Lorelai enough to give her everything she'd ever dreamed of - even a proposal with a thousand daisies. Had they met a little later in life, it's possible that these two could have worked out, in the end. But at the time they were engaged, Lorelai wasn't mature enough, or ready enough, for that kind of commitment. And when they meet again, it's clear that the feelings are still there. But sometimes, that's not enough. We just hope Max, who disappears after the third season, got the happiness he deserved.