Summary

• Lorelai's romantic relationships had a significant impact on her complex family dynamics and the relationships she had with her parents and daughter throughout the series.
• Some of Lorelai's boyfriends, like Rune and Jason, were ill-fitting and had negative effects on her life and overall happiness.
• Luke Danes was the ultimate love interest for Lorelai, as they understood and ed each other, making them the perfect match.

Gilmore Girls has long been beloved for its portrayal of complex family relationships, especially between parents and their children, but romance, and particularly Lorelai's boyfriends can affect those complex relationships. 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-encoming grasp on popular culture.

Lorelai and Rory Gilmore set high expectations for a generation of television viewers, not only in of the relationship they had with each other but also in 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. 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.

Rune Belleville

Although Rune wasn't actually Lorelai's boyfriend, dates don't get much worse than him. 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, 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. To Rune, dating Lorelai is unthinkable. It was confusing why Lorelai even went on the date, to begin with. It's entirely possible that his complaints are because he was roped into a date he wasn't interested in as well. The entire experience is unpleasant for both characters, and it's clear they would have been ill-fitting.

Jason "Digger" Stiles

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. That flirtation didn't lead to Digger being Lorelai's boyfriend at the time though.

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. As rocky as Lorelai's relationship with her parents could be, that's something she couldn't forgive.

Christopher Hayden

Plenty of Lorelai's teenage dating history didn't translate well to Lorelai's boyfriends as an adult. 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. Christopher didn't really know the adult version of Lorelai, only the teenage version.

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 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.

Lorelai is properly horrified 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 and doesn't officially become one of Lorelai's boyfriends after that initial interest.

Paul

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. There's no future for their relationship as soon as Lorelai realizes just how young he is. Although Lorelai did have her immature moments, she continually looked for a stable and mature partner who could understand them.

Alex Lesman

Alex wasn't necessarily one of Lorelai's boyfriends, but that was 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 meet, 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 that 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. It's likely actor Billy Burke had another project, but there's never an in-universe explanation for his disappearance.

Max Medina

Luke Danes may be Lorelai's soulmate, but that doesn't necessarily make him the best boyfriend she's ever had. Max Medina was one of Lorelai's better boyfriends and eventual fiancé. 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.

Luke Danes

From the show 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 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. Luke is the fan favorite of Lorelai's boyfriends and her eventual husband in Gilmore Girls.