Since its debut, Gilmore Girls has always been about relationships - and not generally the romantic ones, although of course, everyone has their romances too. The mother-daughter relationships between Emily, Lorelai, and Rory take center stage, but both Rory and Lorelai's friendships are also hugely important to the series - whether those are long-standing (like Lorelai and Sookie), or brand new (like Rory and Paris).
Despite the show's focus on friendship, there are several promising relationships it never chooses to explore. With some duos possessing compatible dispositions and others sharing remarkably similar histories, it's a wonder that many exciting pairings never came to fruition.
Babette, Miss Patty, and Miss Celine
Babette and Miss Patty are Stars Hollow's resident gossips, a chatty, nosy, and absolutely lovable duo who can often be found talking shop outside Doose's Market or at Luke's. Considering their vivacious and energetic personalities, it's a shame the pair never connected with Miss Celine, Emily Gilmore's ancient personal stylist and seamstress.
Miss Celine's constant monologue relaying tales of Hollywood stars gone by doesn't usually land with Lorelai and Rory, but Babette, and particularly showbusiness veteran Miss Patty, would have eaten it right up.
Dean and Luke
Viewers only see Dean and Luke, two men who hold important and long-lasting positions in Lorelai and Rory's lives, meaningfully interact a couple of times across Gilmore Girls' seven seasons. In season one after Dean and Rory's first breakup, they fight outside Luke's diner when Dean tries to get in to see Rory, and in season five tension between the pair derails a double date.
But couldn't they have gotten along? They're both born-and-raised Stars Hollow residents and they both have serious issues with Jess, which could have been points of connection (or at least forgiveness) after Jess's departure at the end of season three.
Sookie and Caesar
Sookie and Caesar are the only two Stars Hollow residents who viewers get to know as talented cooks, with the former running the kitchen at the Independence and Dragonfly inns and the latter manning Luke's Diner. Both clearly have skills, as Sookie can very often be seen whipping up a suspiciously vast array of dishes in practically no time, while Caesar is often called upon by Luke to run the bustling diner on his own.
Considering Stars Hollow's innumerable seasonal festivals and other highly unnecessary gatherings, the question of why the pair never ed forces to create culinary magic - especially while their colleagues Luke and Lorelai were dating - remains a mystery.
T.J. and Kirk
Kirk is dethroned as Stars Hollow's most irritating resident (bar Taylor) when Luke's sister Liz moves to town and viewers get to know her husband T.J. The goofy, loud-mouthed New Yorker usually turns up at Luke's simply to annoy the diner-owner until Lorelai tricks the jobless T.J. into believing he's the lead contractor for her home renovations.
While Kirk is usually cooking up elaborate and ridiculous business ventures and other plots about town, the dimwitted T.J. would have made an enthusiastic and equally kooky collaborator (or sidekick).
April and Tana
In season four, well before the question of Luke having a secret child is on any character's radar, Tanna is introduced as one of Rory's roommates at the Yale dorms. The child genius starts college at 15 but suffers from social awkwardness requiring her to prepare conversation topics in advance.
She would've been a perfect fit (and perhaps mentor) for April Nardini, the namesake of the season episode "Return of the Prodigal Daughter." Both girls are extremely bright, a tad nerdy, and have friendly (if eccentric) dispositions, and it would have made total sense to see Tanna return as a friend or tutor for Luke's daughter.
Emily and Michel
Although we rarely see them interact, Emily Gilmore, the fussy and critical matriarch of the Gilmore family, and Michel Gerard, the concierge at the Independence Inn and later the Dragonfly, would have made quite the dynamic duo. Both make a habit of pestering Lorelai with elaborate requests and complaints (and both seem to find enjoyment in it).
When they do cross paths, like in season one's "Emily in Wonderland," their similarities and mutual love of finery are played for laughs, but not fully explored. It would have been hilarious for Lorelai to turn up at her parents' house only to find Michel and her mother enjoying a cup of tea.
Jess and Dave
Ask any Gilmore Girls fan, and they'll have an opinion on whether Dave or Zack was better for Lane. The former, a musically gifted charmer, enjoys an adorable and collaborative relationship with Lane in season three until his departure for college in California.
At the same time, Lane's best friend Rory is dating sulky bad boy (and her eventual step-cousin) Jess. Why did Stars Hollow's cutest seniors never have a double date? Dave could have served as a much-needed friend for the equally artistic Jess, who has few allies in Stars Hollow aside from his disgruntled uncle Luke.
Lane and Sophie
Famed songstress Carole King recurs in Gilmore Girls as Sophie Bloom, former New York musician and owner of Sophie's Music in Stars Hollow. Sophie is generally a busy and irritable shop owner, and nearly brushes Lane off when the burgeoning drummer asks to meet for coffee. Before she's able to honor this commitment, Lane drunkenly accuses her of sleeping with Zack, when in fact she's been allowing the rocker to secretly play bluegrass in her shop.
With Lane's love of music proving to be her major character arc, the show could have had its famous guest star move into a more significant role as a mentor for Lane, as Luke is for new father Zack in season seven.
Emily and Mia
Mia Bass, the onetime owner of the Independence Inn and a major maternal figure in Lorelai's life, put up and employed the then-17-year-old when she fled her parents and landed in Stars Hollow. When Emily tags along to Mia's North Carolina wedding in season seven, it's revealed that Emily made the trip once before to ask for pictures of Lorelai and Rory during their absence from her life.
As Lorelai's two mothers in a sense, Emily and Mia share a bond tinged with both mutual iration and jealousy. It would have been fascinating to see the pair's relationship develop, or for a more extensive history between the two women to be revealed.
Lorelai and Anna
Lorelai never enjoys a pleasant relationship with Anna Nardini, mother to Luke's daughter April, with Luke spending most of season six cutting Lorelai out of his burgeoning fatherhood. The two moms only meet when Lorelai shows up at Anna's clothing shop to apologize for hosting April's birthday party.
The brief conversation they share is awkward yet heartfelt, and it would have been an interesting dynamic for the show to explore further. It could have been charming to see Lorelai take on a bigger role in April's life, and bond with fellow single mother Anna at the same time.