Dean and Lisa

Dean Winchester and Lisa Braeden have shared a complicated romantic relationship. They also have a family relationship, which includes Lisa's son Ben. Dean deeply cares for Lisa and Ben and rather die than see them hurt. On multiple occasions, Dean has shown that - of all the women he has slept with - Lisa is more than that: the woman he loves. In season 6, Dean lives with them for a full year. An "Apple Pie" life. Dean's nickname for Lisa is "Lise". Their relationship came to a tragic end when he requested Castiel erase her memories of him.

Background
Lisa and Dean met about 9 years before season 3's The Kids Are Alright. This was about 1999. Back then, Lisa was a yoga instructor when Dean first met her. At the time, Dean was by himself while Sam and John hunted a Banshee. The two hooked up and spent a week together. For Dean, he described it as the bendiest week of his life. For Lisa, it was the best night of her life. After Dean left, Lisa hooked up with a biker from a bar and got pregnant with Ben. Back then she had a type and Dean fit it.

Season 3
When Dean hears about a murder in Cicero, Indiana, Dean gets the idea to visit an old flame. Lisa Braeden, a old girlfriend he hooked up with about 8 or 9 years ago. When Dean appears on her doorstep, Lisa is surprised, and Dean mentions how he knows she loves surprises. An awkward silence passes and Lisa tells Deans this is a bad time right now; they're having a party. Dean says that he loves parties and comes in. Dean meets Ben who is a lot like Dean, which leads Dean to asking Lisa is Ben is his. Lisa tells Dean, Ben isn't his son.

Later on, Lisa finds out that Dean taught Ben how to fight, which angers her. She yells at Dean at doing this and pulls him to the side and asks why hes even still here. She continues one by saying that all they had was one week together and thats it. Dean doens't even know her now and that he has no business with Ben. Dean is looks shocked at this. Lisa is surprised when Ben runs to hug Dean.

When they figure out Changelings are in the nieghbourhood, Dean rushes to Lisa's to get them out. Lisa is still mad at Dean for teaching Ben to beat up a kid (despite Dean's good intentions). Dean offers Lisa a vacation on him, but Lisa is not buying it. Then "Ben" tells Lisa to make Dean go away. Which she does and slams the door on Dean. Lisa forgives Dean later when he brings the real Ben back. He explains what really happened to Ben and his job (which Lisa admits she didn't want to know). Dean asks Lisa again is Ben really isn't his and Lisa answers, no Ben isn't (she did a blood test when Ben was a baby). Dean does look disappointed, which Lisa notes. Lisa kisses Dean and tells him he can stay for a couple more days if he wants. Though with his time ticking away, Dean tells her he has got some work to do and leaves.

In Dream a Little Dream of Me, Dean dreams about a normal life with Lisa. In this dream, him and Lisa are married (or a couple) and shes calling him to have a pinic with her. She continues on by saying that they only have 20 minutes until they have to pick up Ben from baseball. Before she disappears, Lisa tells Dean that she loves him. According to Dean's actions, this isn't the first time hes had this dream. A dream of a normal life with Lisa. This also shows that Lisa is not just any normal hook-up Dean has had. Shes different.

Season 5
Dean returns to see her again in 99 Problems. Lisa is surprised to see Dean again, but noticing his demor, she asks Dean if hes alright. Dean honestly answers no, but hes okay with how his life is gonna go. He continues on how he imagined living a life with her and Ben, happy. Lisa invites him inside for a beer, but Dean tells her he can't. Lisa stops him, and tells Dean he can't just leave after saying all that. She is worried about what he is about to do. Dean tells her things are going to get bad but he is going to make arrangments for her and Ben. Lisa is getting more worried and asks Dean to come inside again and not to do what hes thinking of doing. Dean refuses, saying he has to do it and leaves (not before kissing her on the cheek).

Dean appears on Lisa's doorstep after losing everything he was living for in Swan Song. Dean promised to live a life with Lisa to Sam. When Lisa sees Dean, she is relived to see him and asks, "Thank God. Are you alright?" Dean answers, yes and asks if he can take Lisa up on that beer she offered last time. As Dean walks in, he breaks down crying and Lisa comforts him. Dean usually only shows emotion to people he trusts, so Lisa must be special to him.

Season 6
"You're an idiot. I mean, I know it wasn't greeting-card perfect, but we were in it together."

- Lisa to Dean

One year later, Dean is still living with Lisa. Dean is now a retired hunter, and has a normal job. Then Dean starts noticing werid things around the neighbourhod and his hunter instincts kick in. Lisa begins to notice Dean acting werid, but Dean deinies it. She knows something is up when Dean is going through his weapons, but Dean doesn't give Lisa a straight answer when she asks. She asks if Dean is hunting, and Dean answers hes getting worked over nothing. Dean tells Lisa to take Ben out so he can do a quick sweep of the area. Lisa agrees to do so and leaves.

Then Dean discovers that the Djinn are after him with an added bonus of finding out Sam is alive. In fear of Lisa's safety Dean rushes home and finds it empty. Then Lisa walks in and Dean hugs her in relief. For their safety, Dean takes Lisa and Ben to Bobby's, while he and Sam get rid of the Djinn. Before he leaves, he and Lisa have a talk. At this time, Dean is thinking of returning to hunting and Lisa is disappointed with this decesion. After defeating the Djinn, Dean decides to go back and get Lisa and Ben. He decides to stay with them and protect them.

In Two And A Half Men, Dean and Lisa move, just to be safe and Dean starts to do what John used to do when he was protecting Sam and Dean. Lisa gets slightly annoyed with Dean on this. She knows Dean is trying to protect them, but she wants to live an normal life. Then Sam calls Dean and brings Dean in on a case. When Dean returns home, he finds Lisa in the kitchen. Dean tells her that he wants to keep them safe, but Lisa sadly tells him they can never be safe with him around. Dean feel guilty about that. Lisa tells Dean to go with his borther and come back when he can. With that, Dean leaves and takes the Impala (and his himself) out of retirement.

Though he does miss Lisa which is seen in The Third Man when Dean dreams about her. When Dean gets turned to a vampire, he comes to Lisa's house and watches her sleep. Lisa wakes up to see him standing over her and Dean thanks her for everything shes done for him. Lisa gets concerned and asks whats wrong. Dean tells her hes going to die soon, but Lisa wants a better answer. Dean shoves her againist a wall and hears her heartbeat, but stops himself. Dean's actions frightens Lisa. But the fact that he showed up at her house, shows how deeply Dean care about Lisa and Ben.

After that incident, their relationship starts to crumple. Lisa calls Dean while he under the truth curse and talk about what happened when Dean was a vampire. Dean tries to talk later, but Lisa tells him since he shoved Ben they need to talk now. Dean tells Lisa he can't explain, and Lisa asks Dean if he thinks he can keep everything buried. Dean tels Lisa you knew what you signed up for. Lisa resorts, I did, but I didn't expect Sam to come back. She knew their relationship was over the moment Sam walked in the door, and tells Dean how werid his and Sam's relationship is. With Sam, Dean can never be happy. Lisa is shocked by her own words, but Dean forgives her though. Dean tries to explain his and Sam's relationship, but Lisa cuts him off by saying that she can't be in this with him and hungs up.

When Dean gets a call from Ben in Mannequin 3: The Reckoning, about Lisa being in trouble and Dean rushes home only to find Lisa ready to go out on a date. Lisa lets Dean into the house and its awkward for the two. They mention their phone calls to each other (Lisa: called 6, Dean: atempted 100). Dean tells Lisa he dropped everything to come here, and Lisa replies doesn't want anything. Dean tells her to ask for something. Lisa moves to sit beside him and tell him he knows she can't ask for something, cause she knows what she wants. But she can't have it. Dean tries to apologize, Lisa cuts him off by saying that every time she gets okay, Dean shows up. She finishes by saying shes trying to get over him, and asks Dean what he wants from them. Dean looks at her silently and seems not knowing what he wants from them either.

Then the worst happens when Lisa and Ben are kidnapped by demons. Dean goes out of his mind trying to figure out where they are. Thanks to Balthazar, Dean finds them, but only to find out Lisa is possessed. So Dean starts excercise her, but then the demon stabs Lisa's body. Dean continues to excercise the demon and then rushes Lisa to the hospital. Unable to have Lisa angry at him for putting her in danger, he asks Castiel to erase her memory of him. Now Lisa no longer remembers Dean.