Lorelai Gilmore’s Love Interests Ranked: From Best to Worst

Gilmore Girls might not have been about romance, but plenty of romantic liaisons during the show’s seven-season run. Lorelai Gilmore’s dating history remains a topic of conversation for fans, 15 years after the original series ended. We’ve ranked Lorelai’s love interests from the absolute best to the absolute worst. 

Luke Danes was Lorelai Gilmore’s endgame relationship 

Luke and Lorelai are beloved by Gilmore Girls fans. Their chemistry was apparent in season 1, and by season 5, it was obvious that they belonged together. Luke’s grumpy and responsible nature perfectly complimented Lorelai’s penchant for whimsy and optimism. The couple, in many ways, managed to ground each other. 

They had the perfect mix of similar interests and differences to keep things interesting. The fact that Luke was eventually willing to work through issues with the Gilmore family ensured he was the right man for Lorelai. Sure, the couple had troubles, but they still managed to make it work. Thankfully, they did get married in the end. 

Jason Stiles was actually Lorelai’s love interest that she had the most in common with 

Jason Stiles and Lorelai Gilmore had a lot in common. Her season 4 beau grew up in the same lifestyle, had a similarly rebellious streak, and was quirky, too. Jason was strange in ways different from Lorelai. Their quirky personalities allowed them to get along well. It seemed like a perfect match. 

The only real downside for Jason was that he wasn’t Luke. If Richard had not tried to destroy him, forcing Jason to sue him, things might have been different. If the family and business drama hadn’t happened, we could see Lorelai and Jason marrying. 

Lorelai Gilmore briefly dated a man named Alex 

There was nothing inherently wrong with Alex, but there wasn’t anything particularly right about him. Alex has to be Lorelai’s most inconsequential multi-episode love interest. He appeared in just a couple of episodes before he was phased out. 

One minute, Lorelai and Alex were heading off to New York to see a play and enjoy a weekend in Manhattan. He disappeared shortly after. Alex did have one positive; he loved coffee. His biggest drawback was the fact that he seemingly ghosted Lorelai. Alex is the absolute middle of the pack of Lorelai’s love interests. 

Christopher Hayden and Lorelai Gilmore couldn’t manage to get it right 

Christopher Hayden was spoiled, entitled, and incredibly impulsive. Lorelai Gilmore was the same. While the similarities could have made him one of Lorelai’s most intriguing love interests, it just didn’t work. The couple, who had a long and sordid history, could never manage to get on the same page because they were far too alike. 

Christopher often claimed he wanted to show up for Lorelai, but he could never actually make it happen. Lorelai wanted to want Christopher, but her heart was never 100% in it. His penchant for getting angry and running off meant he wasn’t the right guy for Lorelai. He’s not the worst of Lorelai’s love interests, though. At the very least, the couple had serious chemistry, unlike her worst romantic partner. 

Max Medina proposed to Lorelai, but it never made much sense  

Lorelai’s season 1 love interest has to be one of the most perplexing and polarizing of the series. During the show’s first season, Lorelai met, dated, and broke up with Max Medina. They also got back together, became engaged, and called off the wedding, all before knowing each other for an entire year. The couple jammed a lot of action into a single school year. 

Max Medina was attractive, well-read, and overall a sweet guy. He, however, didn’t spend any time trying to understand Lorelai and only proposed to her because he was jealous of Luke Danes. Even ignoring the jealousy issue, Max and Lorelai were deeply mismatched and didn’t have much in the way of chemistry. The relationship was doomed from the start, and if they had wed, they likely would have ended up divorced in relatively short order. The couple would have figured that out quickly had Max not proposed out of possessiveness. 

While it’s an unpopular Gilmore Girls opinion, Max was the worst of Lorelai’s love interests. Even Christopher, who was problematic in his right, fit Lorelai’s life better.