One of the most iconic mother-daughter relationships made its screen debut on Gilmore Girls in 2000. The connection between Lorelai (Lauren Graham) and Rory (Alexis Bledel) was unique for many reasons: the witty banter, Rory’s coming-of-age story running parallel to Lorelai chasing her dreams, and the inevitable male suitors of the blue-eyed beauties. Though the duo tried to establish some boundaries with one another as mother and daughter, their friendship always prevailed.

As a single mother, Lorelai focuses on making sure Rory has every opportunity in front of her. She wants her daughter to attend college, pursue her own career path, and simply enjoy the childhood she never had. One aspect that may have slipped Lorelai’s mind was that her only daughter would soon be dating. Given that Lorelai got pregnant with Rory at the age of 16, she is a bit of a novice herself when it comes to the dating world. From all the bad dates to the ones who made the cut for the official title, here are the best and worst boyfriends the Gilmore girls made exclusive.

8 Paul

Paul is Rory’s boyfriend of two years in the Netflix reboot, Gilmore Girls: A Year in the Life, but do not fret if you don’t remember him; that was his gimmick. When he accompanies Rory to her childhood home to have dinner with Lorelai and Luke, neither can remember meeting him. Rory often forgets that he is supposed to tag along to places, so he tends to get left behind. This pairing never felt right. He brought little to no backstory, he did not fit in with the rest of the eccentric characters in Stars Hollow, and he is simply forgettable. Rory even mentions several times that she means to break up with the guy, but she forgets! Between Rory cheating on him and his lack of personality, fans were not upset when the two did not work out.

7 Jason

The foundation and appeal of Jason’s relationship with Lorelai was that it was a secret. Though Jason essentially is Lorelai’s male counterpart — he comes from money, he grew up going to the same camps as Lorelai, and he is seen as the black sheep by his parents — Lorelai cannot help but enjoy the fact that her mother would not approve of the match. He, like many of the other men, questions her friendship with Luke. He does not seem to care for the chaotic yet slow lifestyle in Stars Hollow. Lastly, there is nearly no connection between him and Rory. Lorelai’s relationship with Jason seems more strategic and convenient rather than one sparked out of passion and mutual interests. When she called it quits after Jason files a lawsuit against her father, little to no fans were upset.

Related: Gilmore Girls: The Best Characters, Ranked

6 Jess

While Jess is a fan favorite, he simply was not a good boyfriend to Rory. The two begin dating moments after Rory breaks up with Dean. She started to have feelings for Jess, and he took pleasure in taunting Dean with their chemistry — this should have been the first red flag in their relationship. There is no argument that his love for books made him seem like the perfect intellectual match for Rory. However, his aloofness and secret-keeping did not win him any points in the romance department. Their relationship as a couple was short-lived and filled with jealousy and doubt, but their friendship years later made him a redeemable guy. Perhaps if they dated while Rory was in college or even as adults in the revival, Jess would have made a much better match.

5 Max

Having raised a daughter by herself for 16 years, it makes sense that Lorelai has not had very many boyfriends. Max is essentially her first adult relationship, so their quick feelings, dating life, and fast engagement makes sense. Max is a genuine guy, he cares for Lorelai’s wellbeing as well as Rory’s, and he accepts the craziness of Stars Hollow. In short, he seems like the perfect guy for Lorelai. However, Lorelai still chose to walk away before their wedding for good reasons. Luke, aside from being a target of jealousy on Max’s end, brought up relevant questions to her about their living situation, kids, and just her future with Max in general. A bit taken back, Lorelai was unable to answer his questions, so she became defensive of her relationship. Max may have been the right guy for Lorelai, but it was the wrong time to be the rebound into the dating world.

4 Dean

Dean was Rory’s first love, so there will always be a tenderness to their relationship. Overall, he was an incredible guy for Rory. He got along very well with Lorelai, he put a lot of effort into his relationship with Rory, and he paid attention to her interests even when he did not care for them himself. Some will say Dean was possessive of Rory, but that only came up when he felt (rightfully) threatened by Jess encroaching into their relationship. His biggest downfall was that he cheated on his wife with Rory and then pursued an already-tainted relationship with her after his divorce. As a young man and Rory’s first boyfriend, he was every mom’s dream, but as a grown man hooked on his first love, he was not right for Rory.

Related: Why Luke Danes Was the Only Likable Character on Gilmore Girls

3 Christopher

Being that Chris is Rory’s father, a successful and exclusive relationship with Lorelai makes perfect sense. After a couple failed attempts, including Lorelai shooting down his marriage proposal at the age of 16 and an unforeseen pregnancy with his previous girlfriend, the two finally found themselves in the right place and time to begin a relationship. Christopher shares Lorelai’s background as far as coming from money and knowing how to navigate the Gilmore parents, and he also shares her witty banter and musical interests. He appears to be perfect. It is simple bonus points that with him in the picture, Rory has both of her parents under one roof. Unfortunately, Christopher does not fit into Lorelai’s Stars Hollow life. The town has watched the chemistry grow between Lorelai and Luke for over a decade, and Chris, unbeknownst to her for quite some time, cannot compete. Lorelai even admits to him that she wants to want him, but her heart clearly wants Luke.

2 Logan

Logan’s relationship originally started as a no-strings-attached deal, but it inevitably grew into so much more. He often challenges Rory to go out of her comfort zone, he communicates his feelings and thoughts rather than waits for Rory to take the reins on a conversation, and he is honest about his upbringing and privilege. Logan genuinely wants the best for Rory, and he consistently puts in the effort with grand gestures as well as intimate and personal occurrences. Perhaps it is because Logan (aside from the forgettable Paul) was Rory’s only successful adult relationship. He made plans for the two of them to get married, but that ended up being his downfall. Rory felt that he was moving at a faster pace in their relationship, and she wanted to weigh her options with a career. Watching them split up near the end of the series was heartbreaking but ultimately for the best.

1 Luke

The relationship the entire town waited for finally came to be in the season 4 finale. Luke expresses his feelings for Lorelai the same night he has to wrangle a naked Kirk, and fans would not have it any other way. He may not always understand Lorelai’s rationale or bits, but he does his best to go along with what she needs. He has been a father figure to Rory for most of her life even when he and Lorelai were not on speaking terms. Most importantly, he wants Lorelai to be happy. As the series goes on, even when they are not a couple, fans can see that Luke gradually shows kindness towards others. Rory even calls him a “big old softie” when he puts together a birthday breakfast for her in the diner. Little by little, Luke reveals that he cares more about the town, especially the Gilmore girls, more than he initially lets on.