|“||Look. I have no illusions, okay? I know the life that I live. I know how that's gonna end for me. Whatever. I'm okay with that. But I wanted you to know ... that when I do picture myself happy ... it's with you. And the kid.||”|
— Dean to Lisa
in 99 Problems
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. 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'". Their relationship came to a tragic end when he requested Castiel to erase her memories of him.
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 said she hooked up with a biker from a bar and got pregnant with Ben. Back then she had a type and Dean fit it.
Season 3When Dean hears about a murder in Cicero, Indiana, Dean gets the idea to visit an old flame. Lisa Braeden, an old girlfriend he hooked up with about 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 Dean this is a bad time right now; they're having a party. Dean says that he loves parties and comes in. Dean meets Lisa's son Ben who is a lot like Dean, which leads Dean to asking Lisa if Ben is his. Lisa tells Dean that Ben isn't his son.
Later on, Lisa finds out that Dean told Ben to hurt a bully, which angers her. She yells at Dean at doing this and pulls him to the side and asks why he's even still here. She continues on by saying that all they had was one week together and that is it. Dean doesn't even know her now and he has no business with Ben. Dean looks shocked at this. Lisa is surprised when Ben runs to hug Dean.
When they figure out Changelings are in the neighbourhood, Dean rushes to Lisa's to get them out. Lisa is still mad at Dean for telling 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" (changeling) 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 looks 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, he and Lisa are a couple and she's calling him to have a picnic 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 he's had this dream, indicating a level of romantic feelings for her.
Dean returns to see her again in 99 Problems. Lisa is surprised to see Dean again, but noticing his demeanour, she asks Dean if he's alright. Dean honestly answers no, but he's okay with how his life is gonna go. He tells her, he thought living a life with her and Ben would be 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 arrangements for her and Ben. Lisa is getting more worried and asks Dean to come inside again and not to do what he's thinking of doing. Dean refuses, saying he has to do it and leaves.Dean appears on Lisa's doorstep after losing everything he was living for in Swan Song. Dean promised Sam that he would live a normal life with Lisa. When Lisa sees Dean, she is relieved to see him and asks, "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.
|“||You're an idiot. I mean, I know it wasn't greeting-card perfect, but we were in it together.||”|
— Lisa to Dean
in Exile on Main Street
One year later, Dean is still living with Lisa. Dean is now a retired hunter, and has a normal job. Then Dean starts noticing weird things around the neighbourhood and his hunter instincts kick in. Lisa begins to notice Dean acting strangely, but Dean denies 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 that he's probably getting worked up 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 decision. After defeating the Djinn, Dean decides to go back and get Lisa and Ben. He decides to stay with them to 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 about this. She knows Dean is trying to protect them, but she wants to live a 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 feels guilty about that. Lisa tells Dean to go with Sam and come back when he can. With that, Dean leaves and takes the Impala (and himself) out of retirement.
Dean 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 she's done for him. Lisa gets concerned and asks what is wrong. Dean tells her he's going to die soon, but Lisa wants a better answer. Dean hears her heartbeat and his fangs appear, but he stops himself. He also pushes Ben. Dean's actions frighten Lisa.
After that incident, their relationship starts to crumple. Lisa calls Dean while he was under the truth curse and talks about what happened when Dean was a vampire. Dean asks to talk later, but Lisa tells him since he pushed 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 tells Lisa "you knew what you signed up for". Lisa replies, "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 weird his and Sam's relationship is. With Sam, Dean can never be happy. Lisa is shocked by her own words, but Dean forgives her. 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 hangs up.
When Dean gets a call from Ben in Mannequin 3: The Reckoning, about Lisa being in trouble, Dean rushes home only to find Lisa ready to go out on a date. Lisa lets Dean into the house and it's awkward for the two. They mention their phone calls to each other (Lisa: called 6, Dean: attempted 100). Dean tells Lisa he dropped everything to come here, and Lisa replies that she doesn't want anything. Dean tells her to ask for something. Lisa moves to sit beside him and tells him he knows she can't ask for something, because she knows what she wants. But she can't have it. Dean tries to apologize, but Lisa cuts him off by saying that every time she gets okay, Dean shows up. She finishes by saying she's trying to get over him, and asks Dean what he wants from them. Dean looks at her silently and seems not to know what he wants from them either.
Dean's worst nightmare occurs when in Let It Bleed, Lisa and Ben are kidnapped by Crowley's 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. The possessed Lisa taunted Dean by telling him he was Ben's father before stating Lisa really didn't know. Out of options, Dean starts to exorcise her, but then the demon stabs Lisa's body. Dean continues to exorcise the demon and then rushes Lisa to the hospital. Lisa nearly dies, but Castiel, as a favor to Dean despite them being enemies, heals her. To protect Lisa from any further attacks/danger, he asks Castiel to erase her and Ben's memories of him. Dean also threatened Sam if he ever mention Lisa and Ben to him, something Sam agreed too.
- As with most romantic relationships in the series, some fans reacted negatively to Lisa. The actress, Cindy Sampson, had received death threats as a result. Cindy was not the first, nor the last female actress to receive threats from such fans.
- Given that the show was originally intended to end in Season 5, Dean's relationship with Lisa might have flourished, as Sam wouldn't have actually returned to drag Dean back into hunting.
- Lisa can be seen as a parallel to Jessica Moore, Sam's girlfriend. Both women were separated from their respective Winchester due to Dean and Sam's connection to hunting and the supernatural, despite Dean and Sam wanting to live with them in peace.
- Furthermore, both women represented the times when Dean and Sam attempted to have an "apple pie life" and escape the hunting world.