There are a number of factors that make Gilmore Girlsa timeless show that is perfect for rewatching, from the cozy town of Stars Hollow to the sharp and fast-paced dialogue. What truly makes the show so special are its characters, though. Lorelai (Lauren Graham) and Rory Gilmore (Alexis Bledel) are such complex and nuanced characters that their lives are always entertaining to watch, and that there is never a shortage of debate when it comes to the show.
Even almost two decades after it ended, there are still plenty of things about Gilmore Girls about which to share an opinion, from who was right in Lorelai and Rory's massive Season 6 fight, to whether Lorelai was too hard on Richard (Edward Herrmann) and Emily (Kelly Bishop). A major source of discourse among fans continues to be about the romances of Gilmore Girls, from who Rory should've ended up with, to who are the best and worst of the show's love interests. These are the 10 worst Gilmore Girls boyfriends, ranked.
10
Doyle McMaster
Played by Danny Strong
Image via WB
Doyle (Danny Strong) may not have been Paris' (Liza Weil) best boyfriend, but he actually turned out to be a much better match for her than Jamie (Brandon Barash). They had the pre-existing foundation of friendship and a working relationship on paper, so she was really herself with him, and they were ultimately a great pairing. They fit very well together as a couple, and were very in-sync with one another and accepting of each other's quirks.
It really was a disappointment to learn in the revival that Paris and Doyle were getting a divorce. That being said, Doyle was not always the best boyfriend, and he could be on both the best and worst lists when it comes to the boyfriends of Gilmore Girls. When they first started dating each other, Doyle was careless with Paris' feelings, and she had to push him into discussing commitment. Additionally, when Rory got the editor position during the coup against Paris, Doyle's loyalties wavered.
9
Henry Cho
Played by Eddie Shin
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Lane first met Henry (Eddie Shin) at a Chilton party, and they hit it off pretty quickly. He made a significant effort to work around her mother's (Emily Kuroda) rules, but he ultimately dumped her when the rules got to be too much for him to handle. Henry was not a bad boyfriend by any means, but it's hard to look back on him without fixating on the way his relationship with Lane ended.
The worst thing about their breakup was that Henry dumped her in a way where he made it seem like their relationship had never really mattered, and he told her that he had asked another girl to the dance before he had actually dumped her. It was a terrible end to Lane's first relationship, and it makes him look bad, particularly compared to Lane's next and best relationship.
8
Jackson Belleville
Played by Jackson Douglas
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Jackson Belleville (Jackson Douglas) is one of a handful of Gilmore Girls men who make both the best and worst boyfriends list. On the one hand, Jackson and Sookie (Melissa McCarthy) were one of the show's best couples, and in a lot of ways, he was a great husband to her. He was loving and sweet, and they had a lot of the same interests. He was also very devoted to and protective of Sookie, like when she buttt heads with Luke (Scott Patterson) over his cooking at the inn.
On the other hand, though, Jackson made some serious missteps in his relationship with Sookie where he put his own wants over her needs. His worst moment was the reveal in Season 7 that he lied about his vasectomy, but Jackson could be a bad partner to Sookie even before that. He refused to buy the basket that Sookie had worked so hard to make for him just because she hesitated about moving in together, and he got mad at her for opening up to Lorelai about his "four in four" plan.
7
Dean Forester
Played by Jared Padalecki
Image via The CW
Of Rory's boyfriends, Dean (Jared Padalecki) was the worst match for her, but he was the best boyfriend to her, at least the first time around. Like Rory and Lorelai always said, he was the perfect first boyfriend. He was kind, thoughtful, and devoted to her, and he even built her a car. Dean's only real flaw in Season 1 was the way he acted when Rory didn't say she loved him back. After that, though, he became a bad boyfriend very quickly.
At his worst, Dean was possessive, controlling, and very needy. Rory definitely crossed the line with Jess (Milo Ventimiglia) a number of times when they were together, and Dean was justified in the way he broke up with her. Before that, though, Dean played a large part in pushing her away. Later, he was an awful husband to Lindsay even before he cheated on her with Rory (Arielle Kebbel), and he completely dragged Rory down the second time they dated.
6
Jess Mariano
Played by Milo Ventimiglia
Image via Warner Bros. Television
Jess is easily one of the very best Gilmore Girls men, and the best fit for Rory, but he wasn't a very good boyfriend when they actually dated. His best moments with Rory came during his courtship of and friendship with her, before they started dating. He was charming and thoughtful, and he really challenged her and was able to share her love of books. He was also thoughtful and caring with her, like when he brought her food during her night alone.
When Rory and Jess started dating, though, he majorly dropped the ball. He didn't make an effort to plan dates with Rory or do things that she wanted to do, he lied to her about the swan situation, and, of course, he completely skipped town and ghosted her after he learned that he would have to repeat the school year. Jess grew into a character who would have made a great boyfriend for Rory, but at the time, he really fell short.
5
Logan Huntzberger
Played by Matt Czuchry
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This is certainly a controversial one, but Logan Huntzberger (Matt Czuchry) was, more times than not, a bad boyfriend to Rory. Like Jess, he was much better to her before they started dating. It was fun to watch him win her over with flirty banter and helping her on her article on the Life and Death Brigade. Once they got together, there were even a few great moments, like when he defended her to his family and when he helped her put out an issue of the Yale Daily News in just one night.
Ultimately, though, Logan was not a great boyfriend. In every one of his fights with Rory, he was deeply manipulative of her, twisting her words so that she could not be mad at him or disagree with him. He watched her get to her rock bottom without fighting her on it, not when she stole a yacht, dropped out of Yale, or didn't speak to Lorelai for months. He also didn't hesitate to hook up with other women during their fight. The revival was certainly unfair to his character in how he treated Rory, but he was a bad boyfriend long before that.
4
Jason Stiles
Played by Chris Eigeman
Image via The WB
Every one of Lorelai's boyfriends pales in comparison to Luke, but there was always just something off about her relationship with Jason. The way it ended was not his fault at all, and the two of them were put in a terrible situation after Richard's betrayal. That being said, though, Jason was not a great boyfriend to Lorelai most of the time that they were together, and it wasn't a bummer to see him go.
Jason was very set in his ways and focused on himself, and he often failed to think about Lorelai's feelings. Jason, to his credit, generally made an effort whenever Lorelai made it clear that he was upsetting her, but he just didn't really get her. Jason may not have been Lorelai's worst boyfriend, but he was not thoughtful enough to be a good boyfriend, and it was never a question whether Lorelai would pick her family over him.
3
Zack Van Gerbig
Played by Todd Lowe
Image via Warner Bros. Television
The O.C.'s Seth Cohen is such a great TV character that he almost makes Adam Brody's exit from Gilmore Girls worth it, but it is still devastating that Dave Rygalski had to leave. Compared to Dave, no boyfriend of Lane's could have possibly lived up to him, and Zack (Todd Lowe) was particularly disappointing. Zack was great as a friend to Lane. He was sweet and funny, and he and Brian (John Cabrera) were very supportive of her during her rift with her mom.
After Lane and Zack started dating, though, his lack of effort became frustrating instead of funny. He mostly just skated through his relationship with Lane, and even ruined a huge opportunity for the band out of random jealousy when he was the one who had chosen not to write her a song. It was disappointing to see them get married, and to see Zack continue to do the bare minimum once he became Lane's husband.
2
Asher Fleming
Played by Michael York
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In theory, Asher Fleming (Michael York) treated Paris well enough when they were together. He dedicated his book to her, took her traveling with him, left her a printing press in his will, and seemed to really care about her. Still, he is easily one of the worst Gilmore Girls boyfriends. Their entire relationship just felt icky, due to both the massive gap in their ages and the huge issue of the power dynamic of him being a professor and her being a student.
The problems with Asher as a boyfriend primarily stemmed from this major issue. Paris was held back while dating him, and couldn't have a normal relationship for the most part, at first due to the secrecy, and then due to their major gaps in life experience. Whereas the best Gilmore Girls relationships saw the characters becoming massive parts of each other's lives, Paris was the one having to insert herself into Asher's life and grow up too quickly.
1
Christopher Hayden
Played by David Sutcliffe
Image via WB
There is no Gilmore Girls boyfriend worse than Christopher (David Sutcliffe), even focusing strictly on his relationship with Lorelai and not how he failed Rory as a father. Lorelai and Christopher were cute in the flashback episode, and it is clear that they were once a good couple. As an adult, though, Christopher always disappointed Lorelai. He was charming but flaky, and rarely delivered on his grand promises and declarations.
Season 7 tried to retcon Christopher's character by making him the heartbroken one when Lorelai wanted a divorce, but he was never the type who would stick around for her. He promised her in the Season 2 finale to be all in, then left her once Sherri (Mädchen Amick) got pregnant. Later on, he came between Lorelai and Luke even though she was happy, both by asking her for parenting help and then later showing up at her parents' second wedding.
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