25 Years Later, Gilmore Girls Fans Owe Jared Padalecki a Big Apology

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Even twenty-five years after it first aired, remains a popular topic of discussion. During its original run, viewers fell in love with the witty banter and close relationship between Lorelai Gilmore and her daughter, Rory. The show continued years later with a limited series on Netflix, allowing creator Amy Sherman-Palladino to finish the story as she envisioned.

Fans were most eager to hear the four words Amy Sherman-Palladino had always intended to use, but the ending didn’t completely please everyone. Rory’s love life remained unresolved, with all three of her main boyfriends appearing – much to the joy of some fans and the frustration of others. Debate over which boyfriend was the best continues today, and it’s complicated by the fact that none of them were a clear frontrunner. However, there was widespread agreement on who was the least favorite: Dean Forester (Jared Padalecki). After twenty years, it’s time fans reconsidered Rory’s first boyfriend and gave him a second look.

Dean Made Some Mistakes While Dating Rory

At its heart, Gilmore Girls focused on the bond between Lorelai and Rory, meaning romantic storylines were never the main focus. This often resulted in flawed male characters, and Dean Forester was a prime example. He was introduced in the first episode – actually a recast from an earlier, unreleased pilot – and initially seemed like the ideal first boyfriend for Rory. In many ways, he was. Their connection began with a shared reference to the film Rosemary’s Baby, and from that moment on, their relationship quickly developed. Dean truly embodied everything a first boyfriend should be.

Dean was a kind and considerate boyfriend who always respected Rory’s boundaries. He was even accepting of her mother’s unusual personality and showed his dedication by building Rory a car himself. However, like many young people in their first relationship, Dean struggled with insecurity. When Rory wasn’t ready to express her feelings as quickly as he wanted, he reacted poorly, getting upset and rejecting her for not feeling the same way at the same time. While this wasn’t a great reaction, it was understandable considering his age and inexperience.

Dean didn’t realize at the time she couldn’t talk about it, simply because he hadn’t experienced enough to know. But that didn’t make her feelings any less real, and they might become true later on. Rory grew up in a very unusual family where romantic love wasn’t often discussed or demonstrated.

Their relationship definitely had its difficult moments, but it wasn’t a complete disaster for Dean. Rory reciprocated his feelings, and they seemed like a normal high school couple. Though Dean worried about wanting a conventional relationship, being around Rory and her unconventional mother actually helped him grow. Dean wasn’t a perfect boyfriend, but he was realistic – he acted like most high school boys, which is why fans often disliked him, especially after Jess came along. Jess represented everything Dean wasn’t, and his arrival made Dean seem less appealing in comparison.

When Rory first met Dean, they bonded over a shared love of books, but that connection faded after Jess came into the picture. Rory’s growing connection with Jess through literature pulled her away from Dean, and their relationship began to struggle. Dean was understandably jealous, even though Rory ultimately seemed more drawn to Jess.

No One Could Blame Dean For How Things Ended

The show excelled thanks to its realistic conversations and clever nods to other works, while still giving its characters depth. Dean often behaved like a typical teenager, and faced criticism for it, even though he was actually very understanding towards Rory. Throughout Season 2, Rory found herself torn between her feelings for Dean and a growing connection with Jess, who was introduced as Luke’s troubled nephew. Jess was sent to Stars Hollow by his mother after being expelled from his New York home, with the hope that a change of scenery would help him get back on track.

Jess struggled with feeling abandoned and the pressures of being considered a gifted child. His resulting resentment pushed people away, despite his intelligence. Rory was the only one who truly connected with him, bonding over their shared love of books. This created a complicated situation for both Rory and Dean, as Rory had never been emotionally involved with two people at once. She didn’t handle it well. While she still cared for Dean, her attraction to Jess was clear to everyone, including him. This ultimately led to Rory being unfaithful to Dean at the end of Season 2 and continuing to hide her feelings for Jess throughout Season 3.

Rory treated Dean poorly for a long time, and it was especially painful to watch. She repeatedly denied anything was happening with Jess, which was incredibly difficult for Dean. Eventually, he reached his breaking point and impulsively ended their relationship during a town dance marathon, leaving Rory shocked. While the way he broke up with her wasn’t ideal, it was a predictable outcome considering Rory’s behavior. Dean’s biggest mistake wasn’t something he did, but rather that he didn’t have the same quick wit and intelligence as Jess. Rory’s constant manipulation far outweighed this one moment of honesty from Dean.

Dean consistently supported and cared for Rory, but it wasn’t enough to maintain their relationship. Gilmore Girls didn’t take sides or assign blame, acknowledging that everyone involved was young and prone to mistakes. However, it was clear that Rory deeply hurt Dean, and the consequences of her actions would continue to affect the characters for seasons to come.

Dean Left Gilmore Girls For Good Reason

Rory deeply hurt Dean, leading to a quick breakup. He coped by rushing into a relationship with his high school ex, Lindsay, and they married young, both only 19. We briefly saw how heartbroken Dean was before the wedding, and it was clear he still loved Rory, even more than he loved the woman he was about to marry. This was revealed right before he said ‘I do’.

During his bachelor party, Dean had a moment of weakness and, while drunk at Luke’s Diner, confessed his feelings for Rory. He then sadly wondered why she didn’t feel the same way. This came as a shock to Luke, who rightly decided Rory shouldn’t be anywhere near the wedding. It was clear Dean was making a big emotional mistake, all because of his feelings for Rory. She’d abruptly changed her mind about him without talking to him, signaling the end of their relationship. Dean quickly moved on, but later realized it was a huge error in judgment.

Dean faced a lot of criticism, and understandably so. His affair with Rory while still married to Lindsay was a significant misstep. The situation was complicated by Rory losing her virginity to a married man – even though Dean was her first boyfriend – and the show didn’t shy away from acknowledging how problematic that was. This willingness to portray flawed characters and difficult situations set Gilmore Girls apart from many other shows aimed at that age group. Everyone in the series makes mistakes with lasting consequences. While Dean wasn’t a perfect partner, he still evoked some sympathy. It’s likely that without Rory, he wouldn’t have made such poor choices.

Throughout the series, Rory repeatedly created drama in her love life, often repeating the same errors – even continuing a relationship with Logan while he was engaged in A Year in the Life. Despite Dean making his own mistakes, Rory was equally flawed. Dean, as a character, continued to develop, but his storyline was cut short due to issues with the show’s production.

As a big TV fan, I always thought Jared Padalecki was a smart actor to jump ship from Gilmore Girls after playing a love interest for five seasons. He landed the lead role as Sam Winchester in Supernatural, and that show really took off – fifteen seasons is huge! Honestly, though, that success kind of left Dean Forester in the dust. After he and Rory got back together and then divorced, their relationship just didn’t work. Rory kept falling for the ‘bad boy’ type, and Dean realized they were heading in completely different directions. He gracefully stepped aside, which I always appreciated.

First love is truly unique, but a lot of what happened with Dean was beyond his control. Rory repeatedly ignored his feelings, and while he definitely made mistakes and was responsible for his own actions, he wasn’t the villain many fans make him out to be. The question of who Rory should have ended up with will probably never be answered, and that’s why people keep rewatching the show.

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2025-11-10 04:09