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, ive 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.

This isn't a takedown of Jared Padalecki’s performance or an argument that Dean was always terrible. Looking at how Dean’s character evolves - and especially how his darker traits subtly creep in over time - it’s impossible to unsee what the pilot was trying to tell us. From “I've been watching you” to his obsessive behavior and escalating jealousy, Dean’s downward spiral doesn’t come out of nowhere. In hindsight, it's clear the groundwork for his controlling and toxic tendencies was laid in Gilmore Girls long before the drama with Jess or his affair with Lindsay.

Dean's Character Gets Worse & Worse As Gilmore Girls Continues

Dean's Story Starts Strong But Slowly Unravels As His Insecurities Take Center Stage

When Gilmore Girls introduced Dean Forrester, he was everything Rory (and viewers) thought a first boyfriend should be. He was kind, grounded, and had that charming, wide-eyed fascination with Rory’s bookish personality. However, Dean in Gilmore Girls didn’t stay that way. His character quickly shifted from sweet to smothering, especially as Rory began growing and changing. Dean was initially ive of her ambitions, but over time, his resentment toward her evolving identity became clear.

By Gilmore Girls season 2, Dean’s jealousy rears its head, particularly when Jess Mariano enters the picture. Suddenly, Dean isn't just Rory's boyfriend - he’s her emotional gatekeeper, constantly monitoring who she spends time with and how much attention she gives them. His discomfort with Rory’s intellectual world becomes more apparent, and it starts to feel like Dean isn't interested in growing with her, he just wants her to stay the same. The more Rory matures, the more threatened Dean becomes.

Dean’s lowest point arguably comes in Gimore Girls season 4, when he marries Lindsay but continues pining for Rory.

Dean’s lowest point arguably comes in Gimore Girls season 4, when he marries Lindsay but continues pining for Rory. His eventual affair with Rory, despite being married, solidified his fall from grace. Not only did this destroy his marriage, but it also tainted his once-innocent romance with Rory. Instead of communicating maturely or facing his feelings responsibly, Dean spirals into ive-aggressive resentment and guilt.

Even by the time Dean exits Gilmore Girls for good, his character never really rebounds. Unlike Jess or Logan, who at least attempt growth, Dean remains stagnant. He doesn’t try to understand Rory’s ambitions or change his own worldview. His early sweetness fades completely, replaced by a possessive bitterness that undercuts the boy viewers once rooted for. When you watch the show with the full context of his arc, it becomes hard to why anyone ever thought he was the “safe” choice.

Gilmore Girls Warned Us About Dean's Downfall In The Very First Episode

Dean’s “Not Creepy” Line In The Pilot Hinted At Exactly Who He Would Become Later

Dean in Gilmore Girls was introduced as Rory’s tall, sweet, seemingly respectful first love - someone safe and grounded, especially compared to the chaos of her future relationships. However, on a closer rewatch of the Gilmore Girls pilot episode, Dean’s introduction isn’t as harmless as it seemed in 2000. In fact, it contains one moment that now plays like a flashing red warning light: “I’ve been watching you.” It’s a line that many fans brushed off at the time, especially with how casually Dean delivers it, but in retrospect, it’s impossible to ignore how unsettling it actually is.

When Dean approaches Rory at Stars Hollow High, he tells her he’s noticed her reading habits - how she always has a book, how she never talks to anyone, how she seems different. Then he says, “I’ve been watching you,” and, sensing how that sounds, immediately adds, “Not in a creepy way.” But it is creepy. He’s essentially itting he’s been studying her from afar and has decided she’s worth pursuing before they’ve even had a real conversation. It’s framed as romantic curiosity, but it’s built on observation, not connection.

This isn’t to say that Dean in Gilmore Girls was always a bad boyfriend, but it does suggest the series planted the seeds of his flaws from the start.

At the time, that scene was meant to signal Dean’s attentiveness. He notices Rory when no one else does. But rewatching it after seeing where his character arc goes, it feels a lot more like the beginning of a pattern. Dean doesn’t fall for Rory because of who she is, he falls for the version of her he’s created in his head. When she inevitably grows beyond that version, he doesn’t handle it well. His possessiveness and jealousy later in the series can be traced right back to this first interaction, where he essentially treats her as an ideal instead of a person.

This isn’t to say that Dean in Gilmore Girls was always a bad boyfriend, but it does suggest the series planted the seeds of his flaws from the start. The pilot shows a guy who wants Rory but doesn’t truly know her, who observes her from a distance rather than engage with her authentically. That kind of iration can quickly sour when challenged, and that’s exactly what happens across the show. The moment that once seemed like teen awkwardness now feels like a carefully placed clue about the real Dean - for those willing to see it.

Rewatching Season 1 Proves Dean Isn't The Perfect Boyfriend Rory Thinks He Is

Dean's Early Behavior In Season 1 Shows Signs Of Possessiveness That Only Get Worse Later

When you revisit Gilmore Girls season 1, it’s easy to see why Rory falls for Dean. He’s the sweet new guy who gives her a handmade bracelet, builds her a car, and listens to her talk about Tolstoy. However, watching the season again after knowing how Dean in Gilmore Girls turns out reveals a more complicated picture. From the very start, Dean expects things from Rory - her attention, her time, her iration - and bristles the moment she deviates from that.

Dean lashes out when Rory’s schedule doesn’t revolve around him, and he constantly needs to be reassured of his place in her life.

Gilmore Girls episodes like “Rory’s Birthday Parties” and “The Breakup, Part 2” show just how fragile Dean’s confidence is. Dean lashes out when Rory’s schedule doesn’t revolve around him, and he constantly needs to be reassured of his place in her life. He’s easily threatened and quick to anger, even over minor misunderstandings. For someone who was supposedly so secure in season 1, Dean reveals just how much he struggles with not being the center of Rory’s world.

It’s clear in hindsight that Dean’s flaws didn’t come out of nowhere. They were there all along, hidden under a layer of puppy-dog charm and teenage romance. Rory may have believed he was perfect, but Gilmore Girls season 1 proves he never really was.