Later on, he and Sam learned about Amazons and discovered that Emma was Dean's daughter.
Emma was conceived during a night hook up from her mother and father. Lydia was impregnated by Dean and after their night, the next day, Lydia was already in a nine months pregnant state. Madeline and the other Amazons arrive for the ceremony of Emma's birth.
Soon Dean receives Emma in his room and learns that she is his daughter while Sam finds that all the victims were killed by their own daughters.
This one is a bit of a doozy, but the answer is yes. Dean accidentally conceived a child with Lydia, an Amazon who had a one-night stand with the Winchester brother in order to have a child. The child, Emma, was born two days after conception and grows up ridiculously fast.
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.
So to put it bluntly, John Winchester is Ben's real father, making Ben actually Dean's little brother.
Though Dean suspects he is Ben's biological father, Lisa says that Ben's father is a man she met in a biker bar - "I had a type - leather jacket, couple of scars, no mailing address." She could also quite possibly be lying to dissuade Dean's attention from the boy, and discourage any fatherly attention or advice Dean ...
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.
Unknown to Dean, Lydia was impregnated with his child and in just a couple of hours, Lydia was already nine months pregnant. Madeline and the other Amazons came to handle Lydia giving birth to her newborn child and soon her daughter was born.
Dean saw her and was confused by the sudden appearance of a baby but was shocked to see her talk with Lydia. Later on, he and Sam learned about Amazons and discovered that Emma was Dean's daughter.
Cassandra Masters is the daughter of Castiel and Meg Masters and the only known Nephalem to exist, which is a hybrid between a union of an angel and demon, even being part human due of Castiel and Meg's human vessels. Cassandra acts as one of the leading main characters with Sam and Dean.
The ring he wears in season 1 to 5 is a rather plain, silver band that might look like a wedding ring (though where I come from you wear your wedding band on the left hand, but I guess that can be different in different countries), but it is simply jewlery.
Lisa Braeden is a single mother of one, who had a fling with Dean Winchester back in 1999, whilst he was on a hunt in the vicinity. She has a young boy named Ben who shares similarities to Dean, although she has categorically stated that he is not his child.
After Dean's death, she was adopted by Ben Warren and Miranda Bailey.
Mary asks Dean to tell her the truth. Dean tries to avoid it but Mary insists. Dean tells her that he is her son, and Mary is shocked by this. She is more horrified that she raised her children in this lifestyle.
He does have one confirmed child, named Emma, who was conceived after Dean had a one-night stand with an Amazon.
Emma finds Dean, telling him she is running away from the Amazons, but actually intending to kill him. When Dean hesitates, suggesting she could actually leave them, Sam arrives and shoots her.
On multiple occasions, Dean has shown that - of all the women he has slept with - he truly loves Lisa. Before and during the first few episodes of, season 6, Dean lives with the Braedens for a full year, living an "Apple Pie" life. Dean's nickname for Lisa is "Lis'".
In the series finale, after Dean dies, Sam leaves the bunker behind for good, taking their dog, Miracle, with him. Over the years, Sam has a family and a son, whom he named after his brother, grows old and dies of natural causes. After Sam's death, he and Dean are reunited in Heaven.
This is likely a reference to the musicians Richard Tandy and Jeff Lynne, both members of the rock group Electric Light Orchestra. Meg calls Castiel "Clarence." Clarence is the angel trying to get his wings in It's a Wonderful Life (1946).
Cass reveals that he has learned a lot about being human and reveals he had sex with April, leading the Winchester's to be surprised. Dean even goes onto make a joke about "having protection." Castiel goes to eat and Ezekiel takes over Sam saying Cass can't stay because he will bring the angels down on them.
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.
In Byzantium, Sam and Dean outright call Jack their son and God compares Dean killing Jack to a father killing his son in Moriah. Ironically, the Winchesters had started out trying to stop Jack from coming into existence and Dean was the most against and threatening towards him but became the closest to Jack.
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.
And we're not about that life, especially with the history of fridging that Supernatural has had when it comes to their female characters. Sam and Eileen got married. Dean approved. And they all lived happily ever after.