Sam and Dean are unable to form romantic attachments to others, and therefore their love is locked in an eternal feedback loop, referring back only to itself. They don't have anyone but each other (and their father) to love, and since their father's death, they love none but each other.
The first season of Supernatural featured some of the best monsters and moments, but one of the most personal plot points involved the introduction of Dean's first true love, Cassie Robinson (Megalyn Echikunwoke).
Jessica Moore
The two quickly fell in love and were shown to be living together in an apartment. Although Sam was planning on marrying Jessica, he never revealed his hunting past to her, thinking it would be safer.
Dean Winchester & Robin
However, as a teenager, Dean did find love with a girl named Robin. Like always, Dean didn't get to stay with her but they did have a moment where they reconnected their love even if it was briefly.
Dean is four years older than Sam and was always told from a young age to "watch out for Sammy". When a demon killed their mother, it was Dean who carried baby Sam out of the house.
God is the oldest among them and always existed. Chaos came into existence with the absence of Light in an area which was caused when God decided to retreat Himself to a smaller form before beginning to craft Creation.
The finale took place five years after the penultimate episode, according to Jared Padalecki, placing the timeline in 2025. By this point, Dean would have to be 46-years-old, leaving that as his final age. In Heaven, he met Sam about 25 years after his death, meaning Dean would have been 71 had he lived until then.
Like A Virgin is the 12th episode of Season 6.
Finally apologizing, Sam tells his brother, “I should've looked for you when you were in purgatory.” Sam never forgave himself for that. But Dean's forgiven him.
In Supernatural, who does Dean Winchester love the most in each season? The person he loves the most besides his parents is his brother Sam. Most of the sacrifices and bad decisions he makes are due to him trying to protect his brother. Its been a central theme throughout the series.
Someone, or something, has drawn the Winchesters and archangels to a strange device capable of impregnating anything it touches. Sam and Gabriel end up coming into contact with it, and Sam becomes pregnant.
Before dying, John tells Dean, if he can't save Sam, he'll have to kill him, should he become evil.
To this end, it was confirmed that Sam's soulmate was his brother Dean, as they shared their Heaven. This is reconfirmed in the Supernatural finale when Sam's soul ascended into Heaven and materialized next to Dean's soul, making him the first person he interacted with in the afterlife.
At Salute to Supernatural Vancouver 2022 Jensen further reiterated that Dean did not have romantic feelings for Castiel, saying that Dean saw Castiel as a family member and losing was like losing a brother.
Dean appeared less frequently on Gilmore Girls starting in Season 4, as he eventually married Lindsay. Rory didn't react well to the marriage, and at the end of the season, Dean cheated on his wife with Rory, which resulted in Rory losing her virginity.
Cassie Robinson
When her father was killed, she contacted Dean for help and they eventually renewed their relationship by sleeping together, now that she saw the supernatural.
"No Rest For The Wicked" (Season 3, Episode 16)
The shortest season of Supernatural brought with it one of the most graphically heartbreaking season finales. After selling his soul the previous year to save Sam, Dean's time is up, and the hellhounds have come to collect.
After Dean died in the series finale, Sam went on to get married and have a child, whom he named after his brother. While it seems Sam didn't continue to hunt, the show also didn't reveal what his profession ended up being.
Lydia met Dean Winchester, along with Castiel at a bar. She shared a conversation with the Winchester and then went to her house where the two enjoyed a night together. Unknown to Dean, Lydia was impregnated with his child and in just a couple of hours, Lydia was already nine months pregnant.
Rory losing her virginity to Dean at the end of Season 4 seemed like a pretty positive experience—except that, y'know, he was married at the time. But Rory's so oblivious to her own wrongdoing that she doesn't actually seem all that upset by the whole thing, so this probably qualifies as the best of the three.
Their marriage is foiled by Dean's obvious love for Rory as well as he and Lindsay probably not being capable of having a serious relationship, let alone a marriage, as opposed to a relaxed teen romance. They get divorced after she discovers that Dean cheated on her with Rory after reading her letter to him.
In Season 11, Dean suffers from the fact that he unleashed The Darkness upon the world. Although he has every intention of defeating The Darkness by whatever means necessary, he soon realizes he himself cannot harm her, and has developed an unwilling attraction towards her.
Dean plays Patrick where he buys in with 50 years, redeeming 25 to undo Bobby's aging, but he ultimately loses. Remembering the ritual Patrick cast on the poker chips, Dean and Sam try to steal the chips, but fail.
While trying to cope with his impending death and make the best of his final year, Dean begins to start hunting the freed Demons. Meeting a seemingly helpful demon Ruby, Dean learns that he too may become a demon himself if he burns in Hell too long.