Gilmore Girls may have had the perfect set-up for Halloween episodes, but the series only did one in its 7 season run and the installment was a huge missed opportunity. The CW dramedy series Gilmore Girls is a classic cozy TV institution, and as such, the series has its fair share of holiday specials.
But strangely for a show with so many Christmas specials (7 episodes in 7 seasons), the eponymous Gilmore Girls only celebrated Halloween once, and the episode wasn't even a true Halloween outing. Throughout both its original 7 seasons and its divisive 2016 revival miniseries A Year in the Life, Gilmore Girls frequently used special occasions such as Christmas, Valentine’s Day, and even graduations to ground its biggest moments.With its small-town setting and a cast of characters like Taylor Doose who are defined by their love of local traditions and celebrations, Gilmore Girls couldn’t have been better suited to doing a Halloween episode.
So why did Gilmore Girls never do a proper Halloween episode? For whatever reason the series never did get into the spirit of the holiday, wasting its lone Halloween episode on the bittersweet season 6 episode ’21 Is The Loneliest Number’. It’s the one where Rory reaches the titular milestone but is on the outs with Lorelei and if a lot of viewers forgot that episode was set at Halloween, it's more than a little understandable. Where shows like That '70s Show, How I Met Your Mother, and Community went all out for the spooky season, this episode doesn’t make much use of the holiday despite the seemingly obvious potential of a Gilmore Girls Halloween.
Early on in this Gilmore Girls episode, there’s a bit of arguing between Babette (and later Luke) about how Lorelei wants to decorate for Halloween, but it’s just (literal) window-dressing in an outing that is mostly centered around Lorelei and Emily’s competitive attempts to influence Rory. Sure, nothing is spookier in the world of Gilmore Girls than parental manipulation, but it’s bizarre that viewers never get a chance to see Taylor worrying about excessively scary public decorations or to find out what movies beloved local oddball Kirk is showing at his home cinema to celebrate a holiday tailor-made for outcasts like him. It’s a shame that viewers didn’t get another surreal, David Lynch-style film from Kirk to celebrate Halloween, but this is not the only big Gilmore Girls failure which saw the creators miss out on an obvious opportunity.
Before this middling outing, season 5 of Gilmore Girls also wasted a potentially great plot with the messy, dissatisfying temporary break-up of Emily and Richard. Like the failure to utilize Halloween as a perfect set-up for a holiday special, Emily and Richard’s brief breakup epitomizes a recurring issue with later Gilmore Girls seasons. Gilmore Girls often began a new plot well, but soon abandoned the idea that drew viewers in before exploring all of its dramatic and comedic attention. Season 7 of Gilmore Girls may be the most critically hated thanks to the departure of original showrunner Amy Sherman Palladino, but this issue can be seen in effect during season 6's Halloween episode which features Babette’s gruesome Halloween decorations early on, immediately moves in to Luke and Lorelei’s disagreements over her ambitious decoration plans, but then abandons this story in favor of focusing on an unrelated Lorelei-Rory plot that drags on for a few more episodes before reaching a predictable conclusion. It may not be as disastrous as Gilmore Girls’ worst failures, but the largely-Halloween-free Halloween episode does show just how much Gilmore Girls struggled to play into its strengths well before the infamously uneven, fan-theory-producing A Year in the Life changed Rory's character beyond recognition.