Dean Winchester’s troubles in life are much worse than an average human being. He has died multiple times brutally, lost many of his loved ones in front of him, and had literally been to Hell. He had one of the worst fates on Supernatural since he was only four years old when his mother was killed and burned on the ceiling of his brother’s nursery.
Amidst all the adversities in his life, Dean has had some things that have been life-changing for him, in a good way. These things gave him a moment of respite or dug through his self-contempt to make him realize how much he deserves happiness. Now with Jensen Ackles busy developing a Supernatural prequel series, it’s the perfect time to look back over Dean’s best moments.
Killing Hitler
For someone whose job is to hunt monsters, Dean was over the moon for the fact that he got to kill one of the biggest human ‘monsters’ in history, Hitler. A Reddit user, MarieNomad, mentions “Killing Hitler” as one of the best things that ever happened to Dean.
Another Redditor, fourleafclover13, agrees with it and elaborates on it, saying, “He was such a happy puppy for a bit.” There certainly couldn’t have been a better description of the way he acted after killing Hitler. For the next several episodes, he would meet people and the first thing he would tell them is that he killed Hitler with his proud face. It was very refreshing to see him being so happy and proud of himself.
Sam Agreeing To Join Him In Pilot
If Sam hadn’t agreed to come with Dean to find their dad and then later stick around with him to hunt monsters, Dean’s life would have possibly turned out a lot worse than it was. If Sam had gone on with his separate life, Dean would have been utterly miserable and alone for a long time. He desperately needed someone by his side at that stage of his life.
A Reddit user, BackOnTheHuntPod, mentions it and describes why it’s the best thing to have happened to Dean. In their words, “Sam agreeing to help Dean find their father, John, in the pilot episode, way back in S1. Dean had just gone through a break-up with Cassie, and as we know, Dean struggled with self-worth issues. Dean reconnecting with Sam allowed him to eventually learn to love himself.”
Bunker
A Redditor, YEGMusic43, contends, “I don’t know about best but finding the bunker gave the boys the home they never really had. Dean seemed so happy there.” Sam and Dean never really had a home since their house burned down when they were kids. Thus, finding the bunker, a home fit for their hunting life, was definitely one of the greatest moments in the show.
Dean who always had to fulfill his brother’s wishes before taking care of his own was thrilled to have his own room and a few comforts in his life like a bed, shower, and kitchen. It shows how much Dean wanted a sort of stability and domesticity in his life despite being one of the best hunters.
Lisa
Dean lived with Lisa for a year after Sam went to Hell with Lucifer inside his body. He had an apple-pie life with her and her son, Ben, where he worked a normal job, cooked, had dinners with the family, taught Ben about working on cars.
Many fans think that Dean was really happy while living that life and one of them is a Redditor Sancho17, who mentions “Lisa” as the best thing in Dean’s life. Other fans on Reddit like HelloNat96 and longtimeli_irker also agree with this.
Realizing Not All Monsters Deserve To Die
A Reddit fan had an interesting opinion about the best thing that happened to the elder Winchester brother. According to ohheyitsalia, “I think the best thing to happen to Dean was the moment he finally realized that not all monsters are evil or deserve to die. When Dean found out about Sam being psychic and the demon blood stuff, he was pretty awful to him.”
But over time, Dean really grew. He realized that the world isn’t black and white, and he learned to judge the “monsters” by their actions. His on-again/off-again friendship with Crowley, his close friendship with Benny, the way he came to (semi) trust Meg and even risks his own life to help her, all show how much he’s changed.”
Meeting Castiel
Arguably the best character introduction on Supernatural, Castiel’s entry not only changed the course of the show but also had a huge impact on Dean’s life. A lot of fans on the Reddit threat seem to agree on the fact that the blue-eyed angel was the best thing to happen in Dean Winchester’s life.
A Redditor, dinguschungus, explains their opinion, “Imagine a lifetime of people disappearing and dying and suddenly someone- someone who isn’t bound to you by blood or a sense of duty- stays!” Castiel was a powerful angel of the Lord who shouldn’t have cared for Dean one bit but the fact that he stuck by him and stayed loyal to him until his last breath helped Dean in getting over his self-worth issues.
Sam’s Birth
It is no secret that Dean loves no one more in the world than his brother, Sam. This is why some fans contend that his birth was the best thing to happen in Dean’s life. A Reddit user, SailorOfHouseT-bird, comments, “Sam being born. Siblings are awesome.”
Another fan on Reddit, Hotbeebeebooboo, says that one of the two things, meeting Cas or Sam being born is the best thing that happened to him. With Sam’s birth, Dean got someone to share his burdens and to be his “shotgun” for the rest of his life.
Interaction With Mary In Her Mind
Losing his mother like that at the tender age of four was a cause for a lot of Dean’s inner demons. He needed to let go of those demons. In season 12 episode 22, “Who We Are,” Dean gets to have a conversation with Mary in her mind, and a Reddit user, TattooAngel, talks about a particular moment in that scene where he got to work through his mommy issues.
In their words, “I think the interaction he had with Mary, in her mind, did a lot for him. He had such an idea of her in his mind from losing her at such a young age and then all the pressure John put on him to become a hunter and avenge her death but also to fill her role and be a parent for Sam. Confronting Mary and being so honest about all of his feelings for her was a cathartic moment for him.”
Bobby Loving Him As A Son
A Reddit user, kavalejava, highlights “Bobby Singer loving him as a son” as one of the best things in Dean’s life. Dean never really had anyone to take care of him in his family because he has been plagued by his father’s revenge and his responsibility of taking care of Sam. So, the fact that Bobby took care of him, whenever he got the opportunity and loved him as his own son did wonders for Dean.
Another user, dinguschungus, points out, “Those bits of season 5 where Sam, Dean, Cas, and Bobby function as a little team really stand out to me because it’s the first and possibly only time Dean has a strong family. He’s at his worst but he’s also notably good at fighting the fear of abandonment that usually plagues him. He really has people to rely on there and feels secure enough to actually respect other people’s boundaries”.
Cas’ Confession
A Reddit user, AllWhiteInk, says, “don’t know when exactly it happened but finally Dean understood he’s not stupid and much more than “Daddy’s blunt little instrument”. To this, another fan, singandplay65, replies, “It happened with Cas’ confession. After that moment he truly started believing it. Up until then he never did.”
Even though Cas declaring his love for Dean was followed by Dean losing him to Empty, the entire speech was life-changing for Dean. Dean always thought of himself as a killer and undeserving of love. But Cas made him believe that he is worthy of love because in Castiel’s words, “he is the most loving and caring person”.
