Deanna

Deanna is the het ship between Dean Winchester and Anna Milton from the Supernatural fandom.

I Know What You Did Last Summer
Dean and Sam are visited by Ruby, who tells them about a girl named Anna that the demons want. Dean initially doesn't trust Ruby, and thinks that Anna isn't real. But Sam does some research and finds out she's real. They go to the mental hospital where she was staying, and track her down to her families church.

When they find her, she tells them about how she can hear the angels talking and how they talk about Dean. When asked when it started, it's revealed that it's the same day that Dean got out of hell. Ruby then shows up and tells them that a demon is on the way, and they hide Anna, as the three stand to fight.

Heaven and Hell
Dean opens the door to find Anna hands bleeding, and a symbol on the mirror. He checks on her as she asks if the angels are gone. Dean asks if she killed them, and she says that she just sent them away. Dean asks how, and she says that the symbol just popped into her head.

Dean takes Anna to Bobby’s, where Dean takes Anna to the anti-demon room. Dean asks Anna what’s on angel radio, but it’s silent. Dean sarcastically says that it’s not troubling at all. Anna asks if they’re scared, but Dean lies and says that they’re not. Sam calls him upstairs, and he tells her to stay there.

Anna looks out over the night sky, as Dean drives up to her. She looks back at him and asks if Pamela got home okay. Dean says yeah, the whole angel thing got to much for her. Anna doesn’t blame her and suggests that Sam and Dean do the same. Dean says that they’re not that smart, then asks why the angels want him. Anna doesn’t know, and Dean then asks why she fell, since humanity isn’t all the that great, but Anna doesn’t agree. She fell for the feelings and would give anything not to go back. Dean says that feelings are overrated, and Anna says that it beats being an angel. Dean asks how that’s possible, they’re perfect, and Anna says that’s the problem. They’re expected to believe in god even though only four have seen him, and if they don’t they’re killed. She was stuck on earth for 2000 years waiting for a father she doesn’t know, which Dean finds funny since he can relate.

As Dean tries to figure something out, Anna walks up to him. He asks if she’s holding up okay, and she says that she’s trying. She starts to thank Dean for everything, but he stops her. She questions whether or not she deserves to be saved, but Dean says they’ve all done things. She then tells him that she heard what they angels said, and what he did in hell. She touches his face and says that it wasn’t his fault, that he should forgive himself. He tells her that he doesn’t want to talk about it, which she knows, but when he does, there are people who will help him. She gives him a quick kiss, and he asks why. She says it’s a last night on earth kind of thing, and he jokes that she’s stealing his best line. They kiss again, and then have sex in the back of the impala.

Anna asks if Dean is okay, just as the door of the barn swings open and in walk Castiel and Uriel. He tells Anna hello, and that it’s good to see her. Sam asks how they found them, and everyone feels awkward till Sam realizes that it was Dean. Sam asks why, and Anna says it’s because his choice was either have them kill her or Sam. She places her hand on Dean’s arm and turns to Dean and gives him a kiss goodbye. The two touch foreheads, as Anna tells him that he did the best he could.

The Rapture
Dean and Sam are driving the Impala, when Anna suddenly shows up, causing Dean to swerve the car. Dean asks if she tried calling ahead, but she likes the element of surprise. Dean tells her she looks good, and she tells him it's not the appropriate time. She accuses him of letting Jimmy get away, and Dean points to Sam as the cause. She asks if Jimmy told them anything and Dean asks what's going on. Anna explains that Cas got dragged back to heaven for punishment. Dean tells her that Cas had something to tell him, but no one knows what it was. She tells him they have to find out.

I Know What You Did Last Summer

 * Dean says that they need to find Anna.
 * Dean thinks that Ruby used them to find Anna.
 * Dean looks away as Sam tells Anna about her parents.
 * Dean tells Sam to take Anna to the back room.

Heaven and Hell

 * Dean touches Anna’s knee.
 * Dean and Sam discuss Anna’s medical history.
 * Ruby and Anna stand next to each other as Pamela arrives.
 * Dean told Pamela about Anna.
 * Dean watches Pamela and Anna perform the seance.
 * Dean goes to Anna as she screams.
 * When Dean grabs Anna’s arm she flings him back.
 * Dean watches Anna wake up.
 * Dean asks Anna who she is.
 * Dean comments on Anna being higher up than Uriel and Castiel.
 * Dean asks Anna if she’s ready.
 * Dean defends Anna against Uriel.
 * Anna warns them to shut their eyes, and Dean does so.

On the Head of a Pin

 * Anna asks why Cas is letting Dean torture Alastair.
 * Anna asks Cas to stop is before they ruin Dean.

The Rapture

 * Dean remember seeing the symbol Anna drew to send away angels.

When the Levee Breaks

 * Anna tells Cas that Dean was trying to help Sam.

Fanon
The pairing doesn't have a large following, given that Dean has many other ships, and Anna's screen time being only a few episodes.

Fandom
FAN FICTION

WIKIS
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Trivia

 * Deanna is also the name of Dean's maternal grandmother who he is apparently named after.

Variations

 * Deannstiel refers to the ship between Dean, Anna, and Castiel