Dean Winchester and Lisa Braeden have shared a complicated, romantic relationship. They're almost like family, which includes Lisa's son Ben, due to Dean's relationship with the two. Dean deeply cares for Lisa and Ben and would hate to see them hurt.
Dean meets Anna during the fourth season, and protects her from angels and demons and soon discovers that she is an angel herself. Anna is empathetic and sympathetic towards Dean for his undeserved suffering within Hell, and he feels he can relate to her unease of taking orders from an absent father.
In fact, Sam, Dean and Castiel have been linked to various different women over its 15-season run. Some pairings were memorable while others were quite forgettable. Sadly, for a hunter or angel neither are blessed with the gift of love, at least not lasting love but that doesn't mean they don't try.
Dean Winchester (Jensen Ackles)
In the end, Dean (Jensen Ackles) went out the way he always thought he would: Hunting. He was killed in the series finale while taking on a nest of vampires, but his ultimate end would come in the show's final moments, when he was reunited with Sam (Jared Padalecki) in heaven.
Lydia is an Amazon who hooked up with Dean Winchester at a bar and the two made love in bed. She was impregnated by the older Winchester and in just a few hours, she was pregnant with her unborn child.
Dean — Her First Love
It is highly unlikely they've been together romantically in recent times as they seem to have moved on, and he is a happily married family man. For this reason, Dean is most likely not the father of Rory's baby.
Emma Winchester is the daughter of Dean Winchester and Lydia. She is an Amazon warrior, trained to kill her father, but she refuse to go through it and was accepted by her family.
Dean Winchester and Lisa Braeden have shared a complicated, romantic relationship. They're almost like family, which includes Lisa's son Ben, due to Dean's relationship with the two.
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. The brothers are unique in that they are the only soulmates who are family rather than spouses.
Eileen Leahy - Sam's final love (Season 15)
That is until Chuck wiped everyone from existence (“Despair”).
When Dean had first met Ben Dean considered the possibility that Ben might actually be his son. Lisa confirmed to Dean that Ben wasn't his son and his similarities to him was due to her 'type' that she hooked up with that Dean had fallen under.
When Dean died, he left Sam alone, and he hasn't quite forgiven himself for that. Though we know that Sam is okay (he eventually marries and has a son, whom he names Dean in honor of his late brother), Dean is still the over-protective big brother he's always been.
Dean and Crowley had sex.
Supernatural Season 13 has added a new cast member whose surname will be abundantly familiar to fans. Danneel Ackles, an actress who, of course, is the wife of Dean Winchester himself, Jensen Ackles, is set to play a recurring character.
However, his affection for Castiel ultimately won, with Dean shown in tears in Purgatory when he thought he'd lost Castiel. Their reunion was their most intimate yet, as the two didn't hold back on letting the other know that they were truly sorry and didn't want to fight anymore.
Before dying, John tells Dean, if he can't save Sam, he'll have to kill him, should he become evil. The fourth season episode "On the Head of a Pin" reveals that the demon Alastair tortured John in Hell for over a century, with John refusing the demon's offer to stop if he himself would torture someone else.
During the scene in question, Castiel confesses his love to Dean before sacrificing himself to stop Death.
When the Winchesters defeated Chuck, Sam was 37-years-old, and piecing together the montage in the finale of his remaining life puts his age at death to be around 65-70.
Fitting: Ended Up In Heaven
Most fans know that whenever a person dies, they either go to Heaven or Hell. Because Dean died several times in the show, it was only fitting that he not only died in the show's finale but that he was rewarded for his job as a hunter by going to Heaven.
Out of Castiel's three lovers, Meg and April, Daphne is the only one with whom Castiel had a successful relationship, as Meg was killed approximately a year later and April was a reaper tasked with killing him. It is unclear if Castiel remembers Daphne, or whether he cares about her at all.
At the same time, some fans were perturbed that Dean did not reciprocate the feelings, as this implied Castiel's love had been unrequited for all these years. Many were also upset that following the declaration, Castiel was pulled into the Empty which is where angels go when they die.
In the end, neither happened, though Jo and Dean did share a kiss before she died in “Abandon All Hope…” Watch that scene below.
Castiel is a young Seraphim, former leader of his garrison, and youngest angel in all of Heaven. He is the husband of the demoness, Meg Master and widowed father of his daughter, Cassandra Masters.
The most obvious reason why Castiel would gravitate more towards Dean than Sam is because the elder Winchester brother was his mission and his reason for coming to Earth. In the Supernatural season 3 finale, Dean dies and goes to Hell, presumably for good.
Dean and Lindsay eventually get a divorce, and Dean and Rory get into a strained relationship.