The focus of Gilmore Girls was family but Lorelai's boyfriends were also a big part of the show. Here, we rank all of her boyfriends from the series.

Gilmore Girls has long been beloved for its portrayal of complex family relationships, especially between parents and their children. The cult series, 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 throughout the series. While Rory's relationships may have been more hotly contested Lorelai had her fair share of relationships, too.

Updated on June 6th, 2022, by Lynn Gibbs: Although Gilmore Girls is ultimately about the mother-daughter relationship between Lorelai and Rory Gilmore, there's also a heavy focus on romantic relationships. Lorelai's boyfriends varied throughout the original series. From short dates to longtime relationships, some were successful while others went up in flames. In the end, diehard fans know who Lorelai ended up with but she wouldn't have been ready for that relationship without dating some of the men on this list. 

8 Lorelai's Date With Rune Was Horrible

Although Rune wasn't Lorelai's boyfriend, dates don't get much worse than him. 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 his date with Sookie. 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. But to Rune, dating Lorelai is unthinkable. It was confusing why Lorelai even went on the date, to begin with. Thankfully, one date was enough.

7 Jason "Digger" Stiles Was The Lorelai's Male Counterpart

Having a shared history doesn't exactly mean that these two were supposed to be a good fit as a couple in the future. 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.

Fast forward 20 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. While some felt Lorelai should have stayed with Jason, they were never going to work. Especially after Jason betrayed his business partner — who just so happens to be Lorelai's father, Richard.

6 Christopher Hayden Didn't Know The Adult Version Of Lorelai

Speaking of teenage histories not exactly translating well into present-day relationships... As Rory's biological father, Christopher is about as unreliable as they get. 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, and 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. As expected, their marriage was a bad idea and there were more than enough moments that led to Lorelai and Christopher's divorce. These two were good for each other at 16 years old but not as adults.

5 Lorelai Never Would Have Fit Into Peyton Sanders' World

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 season 3 when attending an auction. Jon Hamm's Peyton Sanders turns out to be the son of some of Emily and Richard's ultra-elite friends and hits it off with Lorelai.

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 their date.

4 Paul Was Young But More Lorelai's Speed

One of Lorelai's best storylines takes place in the series' first couple of seasons when she attends night classes for business school to prepare herself for opening her dream inn one day. During 'Run Away, Little Boy,' Lorelai has a sweet, cute flirtation with a fellow business school classmate named Paul. The two never dated but Lorelai didn't rule it out.

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. Although Lorelai did have her immature moments...

3 Was Alex Lesman The One That Got Away?

Alex wasn't necessarily Lorelai's boyfriend but that's the direction they were heading in until he disappeared without a trace. Alex is another date that Lorelai meets thanks to Sookie. 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. Trying new things is one of Lorelai's best traits. They remain together for most of the third season but then, without a word, they're no longer together.

2 Max Medina Was A Great Boyfriend (But Far Too Pushy)

Luke Danes may be Lorelai's soulmate, but that doesn't necessarily make him the best boyfriend she's ever had. Max Medina was arguably one of her better boyfriends and eventual fiance. Out of all the men that Lorelai dates, Max had Lorelai's best interest at heart. 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. Had they met a little later in life, these two could have worked out. But at the time they were engaged, Lorelai wasn't mature enough or ready 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. As wonderful as he was, Max was pushy and rushed Lorelai into things she wasn't necessarily ready for. Although Lorelai and Max were good together, she would have always had lingering feelings for Luke.

1 Luke Danes Was Endgame

From the pilot, it was instantly clear that Gilmore Girls truly had something special in the relationship between the ever-perky and caffeinated Lorelai Gilmore and the grumpy diner owner Luke Danes. 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.

NEXT: Luke and Lorelai's Relationship Timeline, Season By Season

Next 10 Highlights Of The Golden Age Of Television, According To Reddit