Gilmore Girls is widely known for its cozy autumnal aesthetic along with its heartwarming story centered around female narratives. The show follows the titular Lorelai (Lauren Graham) and Rory (Alexis Bledel) Gilmore as they navigate life and love across generational lines that are often more blurred than they appear. While the heart of Gilmore Girls is certainly its central relationship between mother and daughter, The show’s male love interests remain a hotly debated topic of conversation.
From the jealous Dean Forrester (Jared Padalecki) to the patient Luke Danes (Scott Patterson), Gilmore Girls has a real talent for exploring the complexities of romantic relationships. None of the men Gilmore Girls are perfect, and their failures make their breakups and makeups with the Gilmore women even more realistic and true to life. The show begins when Rory is a high school student and Lorelai, in her 30s, runs a local inn. Lorelai and Rory’s life positions introduce them to men from diverse walks of life, with the latter occasionally following her mother’s pattern. After all, like mother, like daughter.
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Christopher Hayden
Rory and Lorelai’s Father’s First Love Is Incredibly Inconsistent
Christopher Hayden (David Sutcliffe) is Lorelai’s first love since high school. Lorelai became pregnant with Rory when she was 16, and her wealthy parents and Christopher’s powerful family urged the young couple to marry for the sake of their stability. Lorelai felt pressured and left her upper-class life in Hartford, Connecticut, for the small town of Stars Hollow, not ready to make the commitment at such a young age. Although Lorelai continues to be a devoted mother to Rory, inspiring her dedication to academics that drives her to attend Yale, Christopher comes in and out of their lives and is incredibly emotionally inconsistent.
Christopher certainly could have tried harder to be an active father to Rory. Although he learns from his mistake and tries to be a better father to Gigi, his second daughter, with his relationship with Sherry (Mädchen Amick), Christopher continues to struggle with the responsibilities of fatherhood. Even in his relationship with Lorelai, he struggles to offer her the stability and unconditional love she needs. He can barely resist his own parents’ harsh criticism of Lorelai, and this leaves him ranked last among Lorelai’s love interests. Gilmore Girls.
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Dean Forrester
Dean Started Out As A Great First Boyfriend, But Things Changed
Dean starts out as a great first boyfriend for Rorywhen he helps her carry her books for the first time on her last day at Stars Hollow High before she transfers to Chilton Academy. Your healthy passion blossoms into something more iconic Gilmore Girls season 1 episode “Kiss and Tell”, when he becomes Rory’s first kiss at Doose’s Market, leading Rory to accidentally steal some cornstarch in her love-sick haze. Their relationship continues with movie dates and book recommendations and ends when the brooding Jess Mariano (Milo Ventimiglia) arrives in town.
Dean takes a much more significant turn for the worse in Gilmore Girls season 4.
Although Rory didn’t get over her first breakup with Dean smoothly amid her growing feelings for Jess, the breakup was always coming. Dean did not fully understand Rory’s aspirations to pursue an Ivy League education and career, as illustrated by his distaste for her constant commitment to college prep work. Dean takes a much more significant turn for the worse in Gilmore Girls Season 4, when he marries Lindsay Shaw (Arielle Kebbel) at just 18 years old. Shortly after their wedding, he sleeps with Rory and begins an affair with her behind Lindsay’s back.
Although the case puts Rory and Dean in a negative light (especially since Rory now only wants him back when he is taken), Dean is significantly more to blame since he was the one who was married to someone else. Dean’s willingness to lie to the innocent Lindsay was a major character flaw, making him arguably the worst of Rory’s love interests Gilmore Girls.
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Richard Gilmore
Richard was generally a good husband and father, but also a product of his time
Richard Used to Be an Empathetic Father to Lorelai when her mother, Emily, criticized her harshly. Richard is also a wealthy Yale-educated insurance businessman who is always ready to defend his wife, daughter, and granddaughter in their wealthy circles. The social scene to which the Gilmores belong has long been critical of Lorelai’s teenage pregnancy, and Richard is always the first to defend his family. This especially comes into play when Richard learns of the Huntzbergers’ harsh treatment of Rory.
However, although he apparently did not commit infidelity, throughout Gilmore Girls it is revealed that he is still in contact with his ex-girlfriend Pennilyn Lott (Linda Gehringer)who he was in a relationship with before meeting Emily. Additionally, Emily often feels conflicted about her purpose in life, often saying that she does not remember a time when she was Richard’s wife. Unfortunately, its dynamics are clearly a product of its time.
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Max Medina
Lorelai’s first fiancé
Max Medina (Scott Cohen) is one of Rory’s teachers at Chilton Academy. He meets Lorelai by chance after a chaotic first day of school for Rory, and the two begin a relationship after a first coffee date. Max is kind and patient with Lorelai, who has strict limits on her love life as a single mother. Max also understands the impact of their relationship on Rory and keeps his personal relationship with Lorelai separate from his treatment of Rory at school.
Rory, although initially hesitant, warms to Max when she sees how well he treats her mother. Max still manages to accomplish the impossible and enchants Richard and Emily Gilmore. Near the end of their relationship, Max begins to express jealousy of Lorelai’s platonic relationship with Luke. This was probably a factor in Lorelai realizing that although Max was great in the role, he just wasn’t the right person for her. Lorelai finally leaves Max at the altar in Gilmore Girls season 3, and leaves town on the day they were supposed to get married.
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Morey Dell
Lorelai and Rory’s neighbor and Babette’s husband
Lorelai and Rory’s eccentric neighbors, Morey (Ted Rooney) and Babette Dell (Sally Struthers) are one of the most wholesome couples. in Gilmore Girls. Known for her husky voice and humorous storytelling, Babette has several unique hobbies and treats her cat as if it were her child. The understated, quiet Morey is the perfect foil to balance her, and their uniquely humorous dynamic creates a sense of unconditional support.
The quirky couple is an underrated pair in the world of Gilmore Girls.
This is seen when Morey is immediately willing to do whatever he can to help with his cat’s funeral in Gilmore Girls season 1. Morey is also very tall and Babette is very short, and he lives in a house with lower sinks and appliances suited to Babette’s height, even though this is a nuisance for him. The quirky couple is an underrated pair in the world of Gilmore Girls, as they experience the simple pleasures of life together while consistently giving back to their community.
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Jackson Belleville
Sookie St.’s Husband
Jackson Belleville (Jackson Douglas) starts off as a lovable curmudgeon who works as a farmer and independent product supplier. He supplies the products to the Independence Inn, where Lorelai works as a manager and Sookie works as a chef at the beginning of Gilmore Girls. The pair’s relationship begins with constant witty banter about the quality of their vegetables and how Sookie can use them in her dishes. Their fight eventually turns romantic when Sookie asks Jackson out on a date. Gilmore Girls season 1.
Although Jackson is another example of Gilmore Girls man who is a supportive and generally emotionally intelligent partner, he is not without his flaws. After the two get married and she gives birth to their second child, Sookie tells Jackson to have a vasectomy to avoid pregnancy in the near future. Although Sookie orders Jackson to have this procedure immediately after giving birth, and it could have warranted a longer conversation, Jackson is dishonest about it. He never has the procedure, resulting in Sookie’s third pregnancy in Gilmore Girls 7th season. Jackson’s dishonesty is the reason he is ranked lower than some of the other men in Gilmore Girls.
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Logan Huntzberger
Rory’s last boyfriend on Gilmore Girls and likely father of her child
Logan Huntzberger (Matt Czuchry) is introduced as a rich playboy who Rory dates at Yale. Logan is initially a womanizer, and Rory agrees to a casual relationship because she has just ended her affair with Dean. Upon realizing that she doesn’t want a casual relationship, Logan immediately recognizes Rory’s worth and commits to a monogamous relationship. All over Gilmore Girls, Logan grows up and becomes increasingly aware of his privilege as he charts his own path separate from his father’s publishing business.
Logan is one of the only characters in Gilmore Girls who offers Rory constructive criticism while remaining a source of unconditional love in her life. He encourages Rory to challenge herself and understand that even though she was raised by a single mother, she is still more privileged than most. Although Logan is arguably Rory’s best match in adulthood, Rory broke off her engagement to him at the end of Gilmore Girlsand it is revealed that she is having an affair with him in Gilmore Girls: A Year in the Life.
Logan is likely the father of Rory’s child.
Logan is likely the father of Rory’s child. While their strong bond and compatibility make Logan a strong contender as one of Rory’s main love interests in Gilmore Girls, his eventual inability to face the pressures of high society are his downfall. He is engaged to an heiress named Odette in A year in the life, and it is strongly insinuated that the engagement was arranged to elevate his status. His lack of integrity in the case is what took him out of the top three love interests in the country. Gilmore Girls.
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Jessica Mariano
Rory’s second boyfriend in Gilmore Girls
Jess is introduced as Luke’s brooding nephew who moves to Stars Hollow after finding himself in trouble at his home in New York City. Jess is sarcastic and harsh, although he is highly intelligent. His love of books is the first thing he establishes with Rory, and the pair’s strong connection comes through easily to them. However, Jess’s emotional immaturity gets in the wayand as a young adult, he is not a good match for Rory.
Later in life, after a stint in California with his father and a published novel, Jess clearly worked on himself and became a strong character as an adult. Even though they are no longer romantically involved, Jess is the only person who encourages Rory to return to Yale after a leave of absence and really work on finding herself. He is incredibly selflessand even reappears in Gilmore Girls: A year in the life with the same purpose of inspiring Rory to believe in herself.
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Dave Rygalski
Lane Kim’s First Boyfriend
Dave Rygalski (Adam Brody) is Lane Kim’s (Keiko Agena) first boyfriend. Dave, a member of Lane’s band Hep Alien, is presented as a compassionate and understanding character who is more than willing to embrace Lane’s Korean roots despite coming from a different cultural background. Since Dave is Jewish and Lane comes from a devout Christian family, Dave even reads the entire Bible in one night to win over her mother and ask to take her to the dance.
Although Dave is seen as calm, collected, and emotionally advanced for his age, his relationship with Lane is short-lived. Dave is scheduled to go to college, when in reality, Brody left to join the main cast of The CO. It’s unclear what Dave and Lane’s relationship would have been like if the character had been on the show longer, but he’s certainly a contender for best love interest in Gilmore Girls.
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Lucas Danes
Gilmore Girls’ best love interest
Luke Danes wins first place as best love interest in Gilmore Girls. Luke is always a devoted friend to Lorelai and a father figure to Rory in Christopher’s absence. Despite his grumpy exterior, he is often incredibly selfless and helpful to various members of the community. He offered unconditional friendship to Lorelai, even when he knew she was not interested in him romantically, and remained devoted to her when they reunited in “Raincoats and Recipes”.
An important aspect of realism Gilmore Girls are its complex characters and, of course, Luke Danes isn’t perfect. He later discovers that he has a daughter from a previous relationship that he was unaware of and immediately enters her life. This causes a brief rift between Luke and Lorelai, rooted in Luke’s constant feelings of remaining a stable pillar for everyone in his life. Luke is always there for Lorelai and Rory, seen through his grand gestures of sewing a tarp for Rory’s rainy graduation party, building a chuppah for Lorelai, repairing her house whenever she needs it, and more.
Luke’s selflessness and honesty is what continues to make his character resonate.
Luke is very supportive and understanding of Lorelai’s trauma associated with her family and high society expectations. At the same time, he is unapologetically himself, and although Emily, in particular, dislikes him at first, she comes to respect his integrity. Luke’s selflessness and honesty is what continues to make his character resonate with generations of Gilmore Girls spectators.