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"Supernatural" 25 Things That Make No Sense About Dean Winchester

Posted by Arni Bergsson on

The world of Supernatural is full of near-constant apocalypses, angels, monsters, and more. With Sam and Dean Winchester (Jared Padalecki and Jensen Ackles) attempting to dam the onslaught, things almost always work out in the end. The bad guys are killed and the world is safe for a grand total of five minutes until the next disaster strikes. Sometimes, however, how the problem is solved doesn’t make a lot of sense even in the fantastical world of the show.

On a show, especially one as long-running Supernatural, there are inconsistencies that emerge. For all the fans can keep track of the minutiae, the creatives tend to be a bit more fallible.

Given the screen time of Dean and Sam Winchester, some things just don’t quite add up with the pair. It could be a slip of the mind, a retroactive change in the continuity, or a million other little things. It all ends up adding up big time in the grand scheme of things. Unfortunately, it leaves these two leads in a bit of pickle because things just won’t make sense around them. Fans have questions that demand to answer after all.

As the older of the pair, Dean ends up with the most question marks around him. This is his right as the big brother. It’s time to go through the series and consider the aspects of Dean Winchester that leave us all scratching our heads.

Without further ado, we present you with 25 Things About Dean Winchester That Just Don’t Make Sense.


This is probably the most nitpicky thing on the list, which is why it’s at the very bottom. Over the years, Dean has been arrested a decent number of times. Given this propensity for trouble with the law, it makes sense that audiences see his records from time to time. The thing is, these records tend to get his stats confused with Sam’s.

Early on, Dean’s height is listed as six foot four. Later, his eye color is listed as brown. These bits are more of a freeze frame bonus.

The question needs to be asked as to why Dean’s records keep getting messed up.


The Winchesters cross dusty backroads and small towns on a regular basis. Yet, the brothers never see the major tourist hotspots of America. Or have they?

In the earliest seasons of the show, Dean mentioned to never seeing the Grand Canyon. Later on, however, Sam mentions a story of him, Dean, and John riding donkeys to the bottom. Dean’s apparently had a flatulence problem.

The writers admitted that this was just a mistake on their part.

Except, now it’s in the show’s continuity. The real question is if Dean did ride a donkey with a flatulence problem down to the Grand Canyon in show.


Dean Winchester has a bit of a strange relationship with technology. He can build an EMF reader by using cannibalized spare parts. Yet he has trouble knowing what an X-Box is or working the computer. While it makes sense that John Winchester wouldn’t be buying a PlayStation, using a computer should be an easier thing for Dean.

If Dean could potentially rebuild a computer, then it makes sense that he would know how to use one? Things have seemed to have eased up since then. Dean even has a smartphone now, which presents a whole other question given the use of burners on the show.


It’s no secret that Dean Winchester’s body takes a lot of punishment. He’s been thrown through doors, cut, almost turned into a vampire, and fought against gods and Leviathans. You tend to get hurt doing things like that. Punishment like that also leaves a mark on the body.

When Dean was resurrected, his body was restored without scar or blemish.

Since then, it looks like that he hasn’t gotten any, even though he has been hurt plenty of times since then. Why isn’t Dean getting the necessary scars since then?


Given how close the brothers are, Dean’s decision to honor Sam’s wish for him to lead a normal life makes sense. If anyone deserves their rest, then it’s Dean and Sam Winchester. The thing that baffles us, however, is why Lisa and Ben out of all the people in the world? Maybe it’s because what they represent or that Ben is actually Dean’s son.

Still, outside of that one time in season three, it’s still an odd decision that Dean would go to Lisa and Ben after everything.

The options were admittedly slim, but why not stay with Bobby? Why not meet someone else?


No one addresses this concerning bit of behavior in the show.

Sometimes, Sam will make one of his classic faces at it, but that’s pretty much it.

The drinking, however, continues to be a concerning aspect of Dean’s personality. When things get truly hard, he seems to find solace in alcohol more often than not. It’s something that should be addressed.


Dean’s life in those years before the pilot episode remains a fairly big question mark. What fans do know, however, is that he was in New Orleans before going to pick up Sam in Stanford. The question that emerges from this is: how?

Supernatural prides itself on running in real time for the most part.

Given the timing of everything, it looks like Dean was in New Orleans around the time that Hurricane Katrina struck.

Either Dean somehow got in and out before evacuations occurred or the show’s timeline is a little out of whack.


Given the dangerous lifestyle that hunters lead, you can probably go for the cheeseburger more often than not. Sooner or later, eating badly for your food at greasy spoons will definitely add up. No matter how much you work out.

It’s surprising that Dean hasn’t experienced health issues in real time from his poor diet.

It looks like, however, he will hit it eventually, as “The Curious Case of Dean Winchester” shows when he’s aged to an old man. Even in his late thirties, however, something should be up health-wise.


Out of the two Winchester brothers (Adam who?), Dean tends to be the one with the witty pop culture quip on the show. Yet his knowledge tends to be a little too perfect at times.

Given his nomadic lifestyle and the whole pesky "getting older" thing, he shouldn’t know everything that he’s referencing.

Yet from Willard to Batman, Dean seems to know it all - and well enough to reference with confidence. It just seems a little too complete. Terrible motels can’t have that much in the way of cable packages, right?


Perhaps the most wanted posters are just not distributed to every small-town cop.


Ben Braeden and his mother represent an interesting conundrum within the Supernatural universe. It was the first time that hints were made to Dean possibly being a father, one day.

It was convincing. Not only does Nicholas Eila, who plays Ben, look enough like Ackles to pass muster, but Dean and Ben are almost scarily similar. It’s the whole nature vs nurture debate. Could Dean’s love of classic rock be genetic?

It just seemed too easy for Lisa to then come out and admit that Dean wasn’t the father.

If he was actually Ben's father, and she had lied, it would make sense that she let him back in so easily after going away again for two years.


What hasn’t happened to Dean Winchester over the years? He’s been run over, knocked unconscious, poisoned, turned into a demon, and that’s the tip of the iceberg.

The only time that audiences have seen him truly messed up is in the season five finale of the show, courtesy of Lucifer.

The other times over the years, however, he doesn’t seem that bad off - physically, anyway.

Even accounting for any training or high pain tolerance, the body will need to rest and recover sooner or later. It never seems to happen with Dean.


Out of everyone on the show, Dean Winchester has the highest onscreen vanquishing count. He has defeated the most monsters on the show. This even includes taking out most of the series season-long Big Bads.

It’s pretty much Buffy levels of impressive. Dean Winchester is the Slayer of Supernatural.

The question, however, is why does it always come down to Dean to give the final blow to the major baddies? Is it because Dean is the older child, the one who is always self-sacrificing? Or is it because of his training?

Either way, it just seems almost too convenient that Dean finishes off the worst of the baddies.


The Winchesters are the personifications of complicated family history and background. John Winchester essentially raised his sons as soldiers. Maybe he and his boys were never going to lead a normal life, but they could have lived a stable one. It leaves Dean with really only Sam to depend on in the world.

Still, for a guy who clearly cares about family, Dean doesn’t seem to try to have those relationships with other family members. To be fair, none of them have worked out well.


Out of everyone on the show, Dean flip-flops the most of whether or not he wants a normal life. Early on in the series, he seems pretty derisive of the concept. Though later, such as in Djinn’s realm and with Lisa, he seems to want that picket fence sort of life. It changes after his stint in Purgatory.

Lately, Dean seems to be fairly ambivalent about the whole thing.

The real question is: does he want that apple pie life? Does he want that life of peace and a steady job? Or is he staying in the hunt forever?


The relationship that Dean has with his parents could, charitably, be described as strained. Between Mary’s violent elimination, his upbringing with his father, and his father’s passing, Dean missed out on a lot of things. Most importantly, however, it left him without closure with his parents.

It tends to rear its head up in pretty interesting ways, such as when he meets Henry Winchester or his mother in the past.

Either way, Jensen Ackles and Jared Padalecki both agree that Dean, whether he knows it or not, needs some kind of closure with his parents. The problem is that he won’t go looking for it or realize he needs it.


Dean Winchester has been subject to a lot of transformations. You name it, chances are he’s been in danger of turning into it.

He’s been de-aged, aged-up, made into a Reaper, turned into a vampire, become a demon, took on traits of a dog, and that’s the tip of the iceberg.

Yet Dean has never suffered any side effects from these various transformations. It just leaves us scratching our heads.

All those transformations and nothing stuck? It doesn’t have to be a big thing. He could be stronger than average or something. There just should be some lingering consequence.


For instance, he knows what a rugaru is in one episode and then acts like he’s never heard of it several episodes later.

Plus, for a hunter, he doesn’t have an open mind. Angels are one thing, but the fae is a different matter entirely. It just seems like an odd sort contradiction to put into a man in that line of work.


Dean is famously the dutiful son in the Winchester family. He dedicated his life entirely to the hunt. Over the seasons, however, it was revealed that Dean was not quite the perfect child that Sam saw him as. While some things can be forgiven due to childhood memories, others can’t really.

The glaring moments are when Dean had seemed to start rebelling against the family business. Moments like playing video games or enjoying his stay in the delinquent boys home, those were the act of rebellion.

It just seems like, even if Sam didn’t know the particulars, there would have been some trace of the experiences left.


As Dean Winchester puts it, he’s “got a GED and a give ‘em hell attitude.”

The question about how and when he got the GED remains.

In the flashbacks of “After School Special”, Sam was a freshman and Dean was a senior in the high school. So why did Dean forgo finishing his senior year and get his GED instead?  Given the apparent timeline, he was already halfway through finishing his senior year in “After School Special”.

With the hunter lifestyle, there could be several good explanations. The show, however, provides none.


In season one of Supernatural, audiences were introduced to Cassie Robinson.

Dean and Cassie had a brief yet intense relationship when he was on a hunt in Ohio. During that time, he informed her about the supernatural and his line of work. Given their past relationship, it seemed like Cassie would reappear at some point.

There has been no mention of the character since that season one episode.

If Cassie was important enough to Dean that he told her about the supernatural, then she deserved another mention.


Though the show does attempt to work in real time, there was some time jumps over the years as well.

Basically trying to piece together the timeline of Supernatural is a tricky thing, never mind the true ages of the heroes of the story.


Given how much Dean loves the Impala, it makes sense that he does do the maintenance on it.

What seems a bit suspect is that he can a) get the parts to rebuild a 1967 Impala and b) can entirely rebuild it from scratch. He does both of those things fairly easily given how quickly he rebuilds the Impala.

According to Chuck, he even adds in things to the rebuild that was purely unique to the Impala itself.

It just seems to strain credulity that Dean would and could so completely rebuild his “Baby” from scratch.


Seasons five and six have a time gap of about a year and a half. During that time, Dean Winchester seemed to have lost a lot of his skillset.

While it is true that people can fall out of practice, it seems a bit shocking that Dean would fall so out of practice in such a relatively short amount of time.

Even if he retired from the life, he is still a hunter and has the paranoia to back it up. At the least, he would have kept a hand in, even if it was relatively minor. Even when a hunter retires, they never really retire.


A lot of actors on Supernatural tend to do double duty. Given the frequency and nature of possessions on the show, it makes sense that there would be a lot of double (triple, quadruple) acts going on. It really is shocking that it took 13 seasons for Dean to get possessed.

There wasn’t an instance of it happening when he was a child or teen or something? Demon Dean was still Dean, just in a demonic state. Being possessed by Michael is something else entirely.

It's just shocking to think, given his near miss transformations and his line of work, that he’s never been possessed before.


What else doesn't make sense about Dean in Supernatural? Let us know in the comments!

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