Was Dean in love with Jo?
Throughout the second season, Jo appears to have romantic feelings for Dean, but Dean does not have feelings for her, it seems to him that she is like a sister to him.On multiple occasions, Dean has shown that – of all the women he has slept with – he truly loves Lisa.She developed feelings for Dean quite as soon as they met, but it seemed clear from the beginning that while Jo was infatuated by Dean, he did not necessarily see her as much more than a sister. He was fond of her but decided to take it no further given the kind of life he led.

Does Dean end up with Jo : In the end, neither happened, though Jo and Dean did share a kiss before she died in “Abandon All Hope…” Watch that scene below.

Do Dean and Jo ever sleep together

In Canon the relationship never got beyond flirting, with Jo turning down Dean's offer for some "last night on Earth sex", before her tragic death in Carthage with Ellen.

Was Cass really in love with Dean : Misha Collins has opened up about Destiel being canon and how their storyline plays out in Supernatural season 15. Destiel shippers assemble. Misha Collins has confirmed that Castiel was "homosexually in love" with Dean in Supernatural.

I love you… Goodbye, Dean." In other words, he confirms that he was always romantically in love with Dean. However, since the scene aired fans have debated as to whether Castiel's speech was meant to be interpreted romantically or not. Now, Misha has confirmed that it was.

Her reappearance in Season 5 led to a revival in the genre. In Canon the relationship never got beyond flirting, with Jo turning down Dean's offer for some "last night on Earth sex", before her tragic death in Carthage with Ellen.

Is Castiel in love with Dean

Misha Collins has confirmed that Castiel was "homosexually in love" with Dean in Supernatural.Dean marries Lindsay in Season 4. While their marriage is a happy one at first, cracks begin to show, and Rory and Dean seem to grow closer.Cheong-san
On-jo and Cheong-san; Nam-ra and Su-hyeok

Although On-jo thought she liked Su-hyeok, it was clear from the start that neither of them was truly interested in the other person. On-jo had feelings for Cheong-san, whereas Su-hyeok fell for Nam-ra.

I love you… Goodbye, Dean." In other words, he confirms that he was always romantically in love with Dean. However, since the scene aired fans have debated as to whether Castiel's speech was meant to be interpreted romantically or not. Now, Misha has confirmed that it was.

Did Castiel tell Dean he loves him : However, he'd come to realize that happiness didn't come from the having of something, but merely from the feeling and the expression. It was then that Castiel tearfully told Dean that he loved him.

Who did Castiel kiss : Out of options, Meg decides to stay back to fight in order to give Sam and Dean a shot at killing Crowley. In order to get a weapon, Meg kisses Castiel, taking his sword. As she pulls away, Castiel pushes her against the wall and kisses her again.

Do Dean and Castiel ever kiss

So yeah, two times he's kissed Cas with no reaction, but Dean just doesn't seem to be able to resist. I also don't think they really talk about the thing that's going on between them, it's just general confusion on Dean's side and well, I guess Cas is mostly just clueless.

Lydia
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.In Wincest fanfic, the majority of fics and fanfic writers frequently portray Dean as the bottom/submissive/gentle partner and Sam as the top/dominant/aggressive partner.

Who is Jensen’s wife : Danneel AcklesJensen Ackles / Wife (m. 2010)

Danielle Turchiano

“Supernatural” is revisiting the world of faith healers and this time the one the Winchesters encounter is played by star Jensen Ackles' real-life wife, Danneel Ackles.