Jared Padalecki’s Best TV Role Isn’t Sam Winchester (It’s in the 26 Year Old Gilmore Girls)

by

For The CW, Supernatural was a defining show. It originally aired on The WB in 2005 and continued when the network rebranded, ultimately running for 15 seasons until 2020. The show was popular not only because of its compelling stories, but also because of the dedication of its stars, Jared Padalecki and Jensen Ackles, who played the demon-hunting brothers Sam and Dean Winchester throughout the entire series.

While Supernatural was a big hit, it wasn’t the first popular show for either of its stars. Before Supernatural, Padalecki had a notable role in a very different series, and some believe it showcased his acting skills even better. He first became well-known playing Dean Forester, a character who wasn’t always loved by viewers.

Dean Was Rory’s First High School Boyfriend on Gilmore Girls

Interestingly, before Jared Padalecki became famous for playing Sam Winchester on “Supernatural,” he actually played Dean Winchester in a different show! For five seasons, he was known as the boyfriend of the younger Gilmore sister in “Gilmore Girls,” a series about a mother named Lorelai and her daughter growing up in the charming town of Stars Hollow, Connecticut.

Lorelai deliberately chose a very different life from her wealthy parents, who lived in Hartford. When she found out she was pregnant at sixteen, she left home to raise her daughter independently. She built a successful life for herself, but never expected her daughter would eventually find herself in the same privileged world she’d rejected years before.

I was so proud when Rory got into Chilton, but Lorelai was in a tough spot – she just couldn’t afford the tuition on her own. It was heartbreaking to see her swallow her pride and ask her mother, Emily, for help. Emily agreed to pay, but with a condition: she wanted to be a real part of Rory and Lorelai’s lives again. Lorelai really struggled with that, accepting the help came with a lot of friction. And honestly, that was just the beginning of everything that was about to happen!

Rory, Lorelai’s daughter, was experiencing the excitement and worry of first love. This happened right as Rory was planning to leave her high school in Stars Hollow, and she met Dean Forester, a thoughtful and steady boy who seemed like the ideal first boyfriend. Lorelai supported their relationship, though she was a little hesitant about how quickly they became close, remembering her own experiences with teenage pregnancy.

Many teen dramas focus on idealized first loves, but Gilmore Girls felt much more real. Rory and her love interests weren’t instantly perfect; they stumbled through awkward moments and misunderstandings, and it took a long time – even until Season 1 – for them to admit their feelings. The show also didn’t shy away from the fact that relationships are often messy and imperfect, which is especially true in the quirky town of Stars Hollow.

Dean Winchester Was a Much More Complex Character Than His Brother Sam

As a critic, I always felt Jared Padalecki, despite appearing in only 63 episodes across five seasons, managed to imbue his character with a genuine quality that his brother, Sam, often lacked. Now, let’s be real, Supernatural wasn’t aiming for gritty realism. The show thrived on the connection between the brothers, and honestly, characters didn’t change much over its long run. It was all about that consistent dynamic, not deep character arcs.

You know, as a big fan of Gilmore Girls, I always thought Dean Forester was a surprisingly complex character. When he first showed up, he seemed perfect – really smart, sweet, and he genuinely tried to get Rory’s pop culture obsession, even if he didn’t always succeed. But things got tricky when he started working on that car for her and, well, laid all his feelings on the line. That’s when their relationship really started to get complicated, you could see the cracks forming.

Rory was surprised by Dean’s actions and didn’t react, which caused a temporary break in their relationship. Like many teenage romances, things fell apart between Dean and Rory. They were both young and overwhelmed with emotions, and lacked the communication skills to work through their problems – a common experience for high school couples.

Dean was upset by Rory’s uncertainty, feeling like she didn’t reciprocate his feelings. However, they eventually reconciled when Rory realized and expressed her love for him. This pattern of disagreements followed by reconnection would become typical of their on-again, off-again relationship throughout the series.

While Lorelai Gilmore consistently demonstrated kindness and a positive attitude, the show Gilmore Girls also didn’t shy away from portraying flawed characters. Dean, for example, was right to confront Rory when he noticed she was developing feelings for Jess while still leading him on.

Rory acted obviously in an attempt to make Jess jealous, unfairly involving Dean in the process. While Dean was justified in calling Rory out, he wasn’t blameless himself. Both Dean and Jess had their flaws and, ultimately, served as stepping stones in Rory’s personal growth. Dean’s biggest mistake was marrying young and then taking his frustrations out on his wife, Lindsay. He never truly moved on from Rory, and this eventually led to an affair between them.

Losing her virginity wasn’t a fairytale moment for Rory, but it felt realistic for the show. Gilmore Girls didn’t portray its characters as perfect; they were allowed to be flawed and make poor choices. Dean changed into someone much less appealing than the boy Rory once loved, and that was intentional – the show explored how people can change and relationships can sour.

I’ve always felt that Gilmore Girls never actually supported cheating, despite what some people think. Lorelai was clearly disappointed in Rory’s choices, and it really showed how easily young people stumble and make mistakes. That whole situation with Rory and Dean – the infidelity – it set the stage for a relationship that was never going to be solid. Even when Dean and Lindsay broke up, it became obvious that Dean and Rory just weren’t a good fit long-term.

Dean had lost his passion for reading and felt stuck in Stars Hollow. Seeing Rory thrive in her new world—especially at a fancy party hosted by her grandparents—made him realize they didn’t have a future together. She had completely embraced the fast-paced, sophisticated Gilmore lifestyle, and he knew he didn’t fit in anymore as her simple, small-town boyfriend.

Having already finished a major arc on another show, the character’s storyline was neatly concluded, and this felt right for his development. Ultimately, Gilmore Girls wasn’t a show about romantic relationships; it always focused on the powerful connection between a mother and her daughter. Dean wasn’t meant to be the ultimate goal, which allowed the writers to portray him as a flawed and realistic person.

Jared Padalecki Returned For Gilmore Girls: A Year in the Life

Dean, like many characters on Gilmore Girls, was emotionally layered and complicated. This is quite different from Supernatural, where Sam’s role didn’t allow for that kind of development. While Sam certainly made errors, his character didn’t really grow or change much – his main motivation always remained his relationship with his brother, which drove the show’s plot.

Sam and Dean Winchester relied heavily on each other, and the show never explored them becoming more independent. Their unhealthy attachment and difficult upbringing actually fueled their success as demon hunters. While Supernatural presented this interesting dynamic, Dean Forester from Gilmore Girls experienced more personal growth and change in just five seasons than the Winchester brothers did over fifteen seasons of fighting demons.

Even while working on serious roles, Jared Padalecki always kept his sense of humor. In one instance, the show featured the Winchester brothers on a TV show bus tour. As Sam learned their next stop was the set of Gilmore Girls, he quickly told Dean they should leave.

The joke was a fun moment for viewers and didn’t impact the main storyline, which is what made it so funny. Jared Padalecki also happily returned to his role as Dean Forester when Gilmore Girls: A Year In the Life was made. Years later, the show came back as a four-part miniseries, following Rory as she navigated her career after college.

While traveling, Rory unexpectedly ran into all of her former boyfriends, including Dean, at the same place they first met. Though their relationship wasn’t meant to last, the show gave it a respectful nod by having them reconnect at Doose’s Market. Dean only appeared briefly, but it was clear he’d built a happy, settled life with a wife and family, away from Stars Hollow.

This scene made it clear that Dean wasn’t supposed to be flawless; he simply represented a crucial part of Rory’s growth into adulthood. While fans likely had their preferences for who Rory should ultimately end up with, each of her boyfriends played an important role. Dean, in particular, experienced a complete and satisfying character development, which is often difficult to achieve in a show that runs for as long as Gilmore Girls.

5 Questions
From Stars Hollow to Supernatural Hunts: Test Your Gilmore-Supernatural Knowledge
Your Top Score
—
Attempts
—
0
0
Report Error

Found an error? Send it so it can be corrected.

Read More

2026-04-06 03:13