Gilmore Girls might be primarily about the relationship between Lorelai, Emily, and Rory (they are the titular 'girls', after all), but their love lives are no small part of the series, either. Whether it's Lorelai's search for love (and her long and complicated history with Christopher and Luke), Rory's first relationships, or their friends' attempts at finding someone to settle down with, romance is just as much at the heart of Gilmore Girls as family is.
Of course, while there were plenty of relationships in there that kept fans guessing, and others that took them completely by surprise, there were also a few that were clearly never going to make it to the end... no matter how much fans wanted them to.
Rory & Dean
Dean may have been the perfect first boyfriend for Rory, but everyone knew that he would only be that 'first' boyfriend, not her last. The Star's Hollow sweetie was kind and handsome, and they had a lot in common as teenagers. But the likelihood of Rory - with all her big dreams of Harvard and traveling the world and building her career - settling down with her first ever boyfriend in her hometown was never good. It was perfect for what it was, but this was never going to be endgame.
Paris & Tristan
This barely counts as a relationship, because it was really just Paris's unrequited crush on the cool boy at school - and it was never going to go anywhere. Tristan himself clearly carried a torch for Rory (although he showed it in ridiculous ways, teasing her and annoying her), and he had essentially no interest in Paris. Fans empathized with Paris, of course, as an unrequited crush on the cool kid is a part of many people's high school experience, but this was never going to turn into something real.
Lorelai & Rune
There was definitely no chance of this turning into something - and Lorelai's first ill-fated date with Rune was one that would go down in Gilmore Girls history as one of the worst!
Lorelai only went out with Rune in the first place because Sookie and Jackson needed a double date, and Rune was rude from the first moment he walked in.
Paris & Asher
Paris and Asher actually managed to have quite an intense and serious relationship for a while, but fans knew that this wasn't going to last - after all, Asher was a professor at Yale, and Paris was a student. Add in the absolutely huge age gap (Paris was barely in her twenties and Asher was in his sixties), and it's clear that this didn't exactly have long term potential. In the end, of course, it actually ended because Asher had a heart attack and passed away, leaving Paris broken hearted.
Emily & Simon
While Emily and Richard spend most of the series as an absolutely devoted pair, there was a brief moment where things went downhill for the Gilmores, and they separated. While this was short-lived, Emily did go on a date during this time, with a lovely man named Simon. And while the date itself was fine, it was clear that she belonged with Richard - especially as she got inside after saying goodnight... and cried.
Lorelai & Jason
Jason was an odd choice for Lorelai from the start. Sure, they had a similar sense of humor and approach to life, but beyond that, there was never enough there. Jason worked with her father, which was a strange dynamic, and the pair lacked real chemistry. It was no surprise when everything went south (and the business relationship had a lot to do with it). And, of course, everyone knew that Luke and Lorelai would end up together.
Dean & Lindsay
It's hard not to feel sorry for Lindsay. She was Dean's rebound relationship, and then he ended up marrying her, which was a terrible decision all around. It was clear that this was a relationship built more on getting back at Rory than anything else, and it quickly went off the rails.
They married extremely young, and Lindsay ended up pushing Dean to take on more hours so they could buy a house, rather than supporting him in going to college. When Dean cheated on her with Rory, fans were disappointed, but not particularly surprised that it didn't work out.
Luke & Nicole
While Nicole was a lovely woman, and seemed like a great partner for Luke in a lot of ways, fans just knew that she was little more than a roadblock to his eventual happy ending with Lorelai. It was also a clear red flag when the two spontaneously married on a cruise, then moved in together (but actually didn't, because Luke continued essentially living above the diner), and then were going to divorce, and then didn't... and by the time they finally did call it quits (because she was cheating), no one was surprised at all.
Max & Lorelai
It briefly seemed as though Max might be a great fit for Lorelai, but in their heart of hearts, the audience knew from the start that this would never work out. For one thing, Max was Rory's teacher, and that was a huge issue from the beginning. It was inappropriate of Lorelai, and caused issues at school. Add to that that everyone knew Lorelai would end up with Luke (or maybe, possibly, Christopher), and the issue of this being an early season relationship in a genre that tends to keep the main character single till the end, and it was clear this wasn't going to go the distance.
Rory & Jess
Rory and Jess may be a fan-favorite pairing, but they were always going to be doomed... at least, the first time around. Jess was great for Rory in so many ways, but he was just too much of a teenage bad boy, and she had a big bright future ahead that didn't have too much space for a sulky kid in a leather jacket. Of course, many fans would argue that if they had been given a chance to reconnect later in life, they would have been perfect together, but that just never seemed to line up.