Relationships unfold as fast as Rory and Lorelai's dialogue in Gilmore Girls, which means that there were quite a few of them throughout the show's seven seasons. The residents of Stars Hollow are generally pretty quirky people, which was only exacerbated when they got romantically involved. Most relationships on the show were doomed from the start, since main characters have a tendency to overlook all the red flags and never think things through.
Despite being mostly dysfunctional, most Gilmore Girls relationships were fun to watch. Unhealthy relationships bring along a whole lot of drama, which is always welcome in the world of TV series.
Luke And Nicole
Luke and Nicole's relationship is one of those storylines that got way too much attention on Gilmore Girls. Luke started dating Nicole after Jess mocked him for longing for Lorelai. Luke then went to do something utterly unpredictable: he went on a cruise, fell in love with Nicole, and even agreed to marry her while drunk.
Luke is not an impulsive guy at all and he would never date someone he has nothing in common with. This relationship dragged on for way too long and we all knew it was bound to end at some point.
Lorelai And Max
Max and Lorelai's relationship might have been okayish if they were teenagers. What these two seem to be forgetting is that they are fully fledged adults. Max proposing to Lorelai was outright ridiculous, especially since they never had any actual conversations about their relationship. It's as if Rory getting a new step-father wasn't an issue worth discussing.
Neither of these two are bad people. It was just really unfortunate how it all panned out. Max only proposed out of fear of abandonment, and Lorelai agreed just because she finds it difficult to say no to people. Lorelai was very inconsistent with Max, but she learned how to stay true to herself later on.
Rory And Jess
Even though there were far more "team Jess" fans out there than "team Dean", there is no denying that Jess and Rory's relationship was toxic. Jess really liked Rory and they had a lot in common, but he, unfortunately, couldn't open up to her and commit.
If it were up to introverted Jess, he would only spend time alone with Rory. She wanted him to become a part of her life, which included attending Stars Hollow events and meeting her friends. Once Jess got the girl of his dreams, he unfortunately didn't know how to be in a relationship. We are all still mourning what could have been.
Lorelai And Christopher
Rory's parents were just teenagers when they had a baby, putting a huge strain on their romance. Despite not staying together, they were always in good relations and clearly still liked each other. They were each other's "what if" person, so they decided to give it a shot again in season 7 and got married.
It would do so many Gilmore Girls characters good if they didn't rush into marriages. Things didn't work out between them after all, but at least they knew for sure this time. It was still a better Lorelai subplot than her relationship with Digger.
Rory And Dean
Dean is everything a teenage girl wants in her first boyfriend: he is considerate, handsome, and well-liked in the community. But Rory was no ordinary girl: it wasn't long until Dean started boring her and she didn't appreciate his rather aggressive advances. When she didn't say "I love you" back, he threw a full-blown temper tantrum and revealed his true colors. There were other times when he was absolutely the worst.
For example, he wanted Rory to spend more time with him rather than to focus on her own ambitions. Despite their youthful differences, Rory held Dean sweetly in her heart. When the two later on reunite and have an affair, Rory refers to him as "my Dean", even though he was, as Lorelai pointed out, "Lindsay's Dean".
Rory And Logan
Logan was by no means the perfect man for Rory, but at least he came from a similar background and shared the college experience with her, which especially delighted Emily. Their relationship was full of drama and ups-and-downs that Rory shouldn't have tolerated.
Rory clearly had some issues stemming from her family of origin, since she always found herself in the role of another woman. Even though they had been through a lot together, they were at least honest with each other every step of the way.
Sookie And Jackson
The fact that a dysfunctional couple such as Sookie and Jackson rank so high on this list just goes to show that there are essentially almost no healthy couples featured on the show whatsoever. Sookie and Jackson's romance started off in such a cute way, but it wasn't long until they started bickering over the silliest things. Perhaps the marital spats were supposed to seem funny, but they were mostly really hard to watch.
Sookie really got worse and worse, especially after she started working for Lorelai. The two went behind each other's backs a lot, but they managed to weather any storm, which is also worth something. They have a big family together and there was no talking of divorce in sight.
Lorelai And Luke
It's funny how these two decided to marry left and right, but it took them so long to finally find a way to each other. Luke and Lorelai complement each other really well. Luke loves taking care of her and she brings a little spark to his overly-realistic outlook on life.
For seasons, we had to watch Luke pine for Lorelai and when they finally got together, they still didn't manage to make it work. All turned out well in the end though: Lorelai finally married him in Gilmore Girls: A Year In The Life.
Richard And Emily
Lorelai's parents are clearly both products of their time. Emily always puts Richard's needs first, but gets little respect in return. He doesn't take her social events seriously and keeps his lunch dates with his ex-fiancé Penny Lott to himself. When Emily started standing up for herself, the couple almost divorced.
There was definitely a lot of room for improvement in this marriage too, but these two decided to stay together through thick and thin. They also shared some interests, which further strengthened their relationship.
Paris And Doyle
Paris found her match in Doyle and they make for an extremely quirky, yet lovable couple. While most find Paris's intensity insufferable, Doyle adores her for it.
They got married, but were unfortunately in the process of getting a divorce. Die-hard fans were pretty upset when the revival didn't elaborate on Paris and Doyle's future. Some are speculating that they will reconcile and have a baby. After all, Paris did say that she is late on the revival. If that is where they are headed, they are definitely the most successful relationship of them all.