Gilmore Girls Set Up Dean's Downfall In Its Very First Episode & It Took Me 25 Years To Realize It

Upon first viewing Gilmore Girls, Dean seems like the ideal first boyfriend - an illusion that subsequent rewatches shatter almost immediately. Dean was sweet, attentive, and - at least at first - appeared to be the safe, supportive choice for Rory Gilmore. As Stars Hollow’s resident tall, floppy-haired heartthrob, Dean quickly won over fans in the early 2000s. However, after rewatching the pilot decades later, I realized something unnerving: the show may have been warning us about Dean’s trajectory from day one. While many of us rooted for Dean in season 1, Gilmore Girls quietly planted the seeds of his eventual downfall in the very first episode, and the signs are easy to miss unless you're paying close attention.