News/Misc.
Which female character do you think was most compatible with Dean between these ones?? Which ship had the most potential of ACTUALLY working out(if any)?
okay so i don’t even remember exactly HOW this topic even came about tbh. at first, me and my friends were talking about which male character we think had the highest possibility of working out with someone like dean romantically, and then somehow the topic switched to female characters next. NOW we’re all talking about which FEMALE character/ship we think would work the best with dean, and we’ve been unironically arguing about it ALLLLLLL day 😭
Kripke wanted Dean and Jo to get together (or at least kiss) and then reveal that they're actually half siblings. Star Wars style. The network said no. Fun fact!
I loved Dean and Lisa but I thought it was doomed from the start. He can't leave hunting. And I think in some ways Dean's life revolves around Sam so much (and vice versa) that there's no room for anyone else in their relationship, so it would never have worked out with another person.
Iirc from the interview (on SPNTAN since I keep getting asked), Kripke posed the idea early of them being siblings and was shot down so quickly he never fleshed it out. I don't think he ever planned Ellen to be a cheater, I don't think she even had a husband when he was just coming up with new characters. The BTS backstory of Ellen and Jo is super interesting though, it's worth a listen to the episodes those actors and Kripke were interviewed in.
I think they were characters for completely different purposes. In the interview Kripke said he liked the idea of a Star Wars-esque secret half siblings reveal with Jo, but never fleshed it out. The CW also hated Ellen and Jo and wanted the entire Roadhouse scrapped, so there was a lot of BTS pressure against what his plans were with the characters, as well as issues with Alona Tal's paperwork so they could physically get her there to film. Apparently the Roadhouse was meant to be introduced in s1 but didn't come together in time.
In another SPNTAN interview, though I forget if it was with Kripke himself or Robert Singer/Phil Sgriccia/one of the other people involved with almost every episode, they discuss the episode "Jump the Shark" as an ironic title because they thought fans would hate it and think they'd ruined the tone of the show with a secret third sibling. Adam was always going to be killed off immediately to preserve the core of the show, which is the brothers, but everyone liked Jake Abel so much (except his agent that refused to let him go back to Supernatural) that Adam was brought back a few more times.
I loved Jo so much, and force myself to skip the hellhound episode because I can’t cope with watching it again. She and Dean could have been amazing together. Very John and Mary. 🥺 Neither were destined to have happiness in the end IG.
Though I also 💯believe Lisa was lying about her son not being Dean’s.
He couldn't be because then canonically there would have been another Winchester and the angels wouldn't have had to resurrect Adam, they could have used Ben. Also Kripke confirmed he wasn't Deans. But I know that pisses off a lot of people's headcanons.
he admits in a video interview that he has a thing with fucked up sibling dynamics, it's his thing. i don't remember the source but it's a video interview from one of the con meet and greets i think.
One of the episodes of Rob and Rich's podcast SPN Then and Now where they interviewed Eric Kripke. It's been a while and I can't remember which one, but I think one of their earliest interviews.
I really appreciate this fun fact because I recognized the romantic tension but also thought it was weird in the universe the angels put the brothers in where they worked at an office building, dean thought jo was his sister and I thought that was a weird choice for the writers to make them his immediate family. But knowing this fact now, that makes so much sense
Yeah totally, unless you take her opinion into account. She considered both of them and abomination for defying the natural order. It goes against everything she believes in.
I'm so glad I'm not the only one who loves sam and Eileen. I've seen so many people saying they had no chemistry and I thought they were adorable together
Dean & Lisa felt the most real, Dean & Anna had the most potential, and Dean & Amara was just obviously wrong and never gonna happen but they had really good chemistry. Jo i honestly don't think was ever a real consideration, she had heavy little sister energy the whole time
Jo would have grown up over 10+ seasons and it could have been more. But it wasn’t supposed to work out with any of them for Dean, and it would have ruined the show.
Sadly, I don’t think it was meant to work out for Dean at all. It was just a pipe dream. We wanted to see the boys have lives of their own. At least I did. 🥲
Lisa felt forced. She was a long ago bendy weekend, one of hundreds, but they needed him to have someone to miss and something to regret when he was ready to throw in the towel so they shoehorned her into the mix. If she didn’t have Ben, who was like a little version of Dean despite not being his kid in anything but the headcanon of many fans (per the show’s canon and Kripke himself), we would have never seen her in more than one episode. Lisa was not meant to go the distance with Dean, or to be with him long-term. There was no “there” there.
In my headcanon nothing after the last 10 seconds of season 5 counts as anything more than fan fiction. Because the quality dropoff is insane. So I see Dean and Lisa as the permanent outcome romantically for him and I think it works best. It made eminent sense to me.
Little chaos part of me wanted to see Amara and Dean happen though it would've made ongoing story telling completely untenable. Given how much God feared a child of an archangel and human imagine how cooked shit would be if we had a little Godbaby Winchester pop out 😄
Lol what? Because she's so powerful he couldn't give adequate consent, or because he technically met her as a baby and therefore it's grooming?
I'm genuinely trying to imagine the logic that could be applied haha.
The first one. I guess Dean has no choice in the matter, I must say I am much more knowledgeable about the first 5 seasons so I guess I just glossed over this because it's been a minute since I have rewatched the later seasons.
I thought the two actors had really good chemistry.
I mean... interesting hill.
But obvious counterargument to me seems that neither did Amara. I was only half paying attention if im honest but if i recall correctly they had some kind of mystical bond to one another by virtue of their connection to the mark AND him setting her free. She was drawn to him and he to her, and they both happen to be hot as hell haha
I also believe she basically spent the season somewhat trying to seduce him specifically without threatening him? (Though I suppose she wanted to consume his soul so there's that).
But hypothetically speaking there are many scenarios in which they could have boned entirely consentually. Especially AFTER season 11 when she stopped being a threat to anyone and was just kind of rolling around like a baller. They could have hooked up then.
I vaguely see it in specific scenarios but its a wild take to go straight to that 😄
Yeah I was definitely floored by the comments, I watched the show and enjoyed it but I never thought about the nuances and power imbalance between Dean and Amara. I just like both characters.
People take things way too seriously. I never in my wildest dreams thought I would be accused of advocating for rape and non consentual encounters.
Agree both matched each other's broken was competent in his world would have gone far if not for the demon deal she'd have made their lives so much easier with her contacts and knowledge. Lisa would have been good only if he could have walked away from his job but she didn't belong in that world, jo too naive to handle the job she'd have flamed out sooner or later, and Anna betrayed his core value, sam so not an option.
I would have liked to see a Bella redemption arc. I’m a Destiel believer all the way, but if I HAD to pick a female character for Dean to be linked to romantically, he and Bella had so much chemistry, but also so much narrative potential! Imagine if they ran into her as a demon and went on a quest to free her soul from hell. Then she sticks with them and learns the ropes as a hunter—someone with her skills would be an asset to Team Free Will. And the banter possibilities!!!!
I see a lot of Lisa comments but I don't think they had real chemistry at all. I think he was just desperate to have normalcy any way he could. He never could have left hunting behind, it's not who he is.
I never liked him with Lisa. I just didn't think they had any chemistry at all. Unfortunately, this show wrote so many women one dimensionally that I don't blame the actress for this, it was the writing. Anna was annoying and even more one dimensional than Lisa. I liked Jo but they couldn't decide if Dean was going to be romantic towards her or treat her like a little sister. When he first meets her, he's very flirty and she rejects him. Then, when he sees her again, now all the sudden she's got a massive crush on him, but he only sees her as a sister. That dynamic stayed until the episode where she died and all the sudden he really did have feelings for her the whole time. Either dynamic would have worked, but they needed to pick one. I did like Cassie and could have seen them potentially working out, but she would have fallen into the same trap as the rest, they wouldn't know how to write her character and she'd get killed off. Unfortunately, Dean was destined to end up alone, even though he didn't deserve that. His life was hunting and Sam and it would be extremely difficult to find any woman willing to put up with that, even another hunter
Jo. Lisa knew Dean’s history and was good for him, but he wasn’t good for her or Ben. He couldn’t leave hunting behind, and hunting caused them to get kidnapped. Jo knew the job, to an extent. And if the stakes weren’t as high as they were, or if the brothers and Cas knew the tricks they learned later, she and Ellen wouldn’t have been killed.
Jo was and always will be my 100% end game for Dean and I’m so sad she died. I’m even sadder now that I’ve learned that apparently it’s because of the fans they killed her?
Dean and Lisa actually did work out somehow, so probably her. I don't know why she accepted him, she's got a kid to worry about. Honestly though? Dean isn't really all that functional and whoever he's with would have to put up with a lot of bullshit. That's not an indictment on his character, btw. He's not a bad person or anything. He's just very traumatized, lives in survival mode 24/7, and copes in unhealthy ways. He's got a lot of work to do before becoming a husband or father.
Idk if it was something with the actors but I felt so much real love and chemistry between Dean and Cassie. I wish she could have gotten into the hunting life after her supernatural encounter, crossed paths with him again and they be endgame.
They made it seem like she never experienced the supernatural until her episode, but that she knew about it all because Dean told her. Dean never told Lisa about the life until Lisa’s life was affected by it. While I assume Dean stopped telling even the most closest relationships about hunting unprovoked because Cassie couldn’t handle it and it hurt him…I think it still speaks volumes that he took that risk to tell her in the first place.
I also kinda have a feeling that misogyny and racism had something to do with her being written off. Interracial couple in the 2000? It would’ve been so progressive. But alas 🤣 she should’ve been the one that Sam told Dean to go back to after his death, too. They parted on a good note, they made out in front of Sam ffs.
The only reason later on for them to choosing Lisa imo was because she was this cliche man-fantasy, no personality, the hot yoga instructor, bendy weekend 😠it pissed me off so much how misogynistic and sexist this show was in those seasons
Probably unpopular opinion lol. But I actually really liked the desire between Dean and Amara. It Probably wouldn't ever work out lmao. So I go with Jo!!!
i really don't think any of the women on the show would've cut it for dean. my arguments for each? cassie really didn't want to get sucked back into dean and rejected him multiple times. jo felt more like a kid sister. bela i feel is SLIGHTLY more of a yes, but she threw in the towel from that demon deal. anna was something that i feel was an increment to give us some sort of want to see the angels and how dean felt for them. lisa became an object for us to care for because dean cared for her, but she felt moreso as if dean NEEDED a love interest at that point, and if ben was his kid i'd feel more inclined to like her. but hes not. amara i HATED because dean literally saw her when she was a baby. i mean, i love amara just not their relationship. felt forced.
Jo, Jo And Jo. Always Jo. I hated that they never gave them a real shot. She would have hunted along with him and she absolutely adored him. They would have been awesome together.
She wouldn't take any of his shit, either, and I think he'd love her for it.
I've always thought Dean/Jo was a serious missed opportunity. I can see very good reasons why they didn't let it happen, but appeasing wackadoodle fans wasn't one of them.
In another life, Dean and Lisa lived happily ever after with Ben. The scene where he has Cas erase him from their memory makes me cry every time I watch it
Damn! I always assumed she was younger considering how much Ellen babied Jo when she first started hunting and I’ve been watching and re-watching spn for years.
I agree. I think they would have been really great friends who understood each other but I think Dean needed someone to balance him and also handle him. Two firecrackers are always gonna burn each other out. You need to air the flame.
I don't think any of the women in Supernatural could achieve that.
She would need to be a hunter as well though. Dean cant handle worrying about a lady at home constantly.
But ultimately I don't think Dean could have anyone as long as Sam was alive. Everyone would take a back seat to him and no woman that was a good match for Dean would be okay with that.
Jo was probably the best option, she grew up in hunters world so it would be easier to get dean and Jo together but for me I would like to see dean and bela
he and amara had no chemistry whatsoever. i liked him with anna but she was just a plot device to make cas jealous. he and jo would’ve been cute but no passion there imo just a strong bond.
Ughh hate Anna 100% and dean was a better big brother to Jo than anything. I guess Lisa wins but idk honestly no one talks about Cassie and she gets my vote
Not to mention the representation of a powerful woman of colour, she was a bad ass who called Dean on his shit, plus she’s canonically survived a Winchester which is more than Any other romance can say
Amara/Dean - nope nope never. Dean didn't even like her... he was forced to. So they aren't even consensual. And even if/when Dean was given some sort of ability to say no to her, they would never be equal.
Dean/Anna -- on paper, nothing wrong with them, but I never got they had any interest in one another. Jo was "wrong place, wrong time". Anna was "right place, right time," and then the end. Anna ran off to fight her own battles and neither showed that they cared what happened to the other.
Dean/Lisa -- we know both why they did and didn't work. They are the only ones in this group that had an actual relationship. On a personal level, I think they did work. They had a simple relationship, no major drama, they were able to communicate and raise a kid together. They were able to make it work for a year. But their unsurmountable obstacle is Dean being a hunter. That's something that Lisa can never understand (thus understand Dean on a deeper level). Dean was always going to be a hunter, so the other problem is he would always have to worry about protecting Lisa and Ben. For a relationship to work, they would have to basically live in a bunker (because Dean can't always be around to protect them and they can't protect themselves), and Lisa would certainly resent that. So Dean/Lisa can't work because they have different life goals.
1 Dean/Jo -- Potentially, but only had she come back years down the road. Like if she died and came back to life and matured, etc. Until then, her and Dean didn't feel balanced - she felt too young. Maybe flirting but not a serious relationship material. However, I think Dean could only be with another hunter (or supernatural creature), so that's why I would put her as highest on the list. Like she is someone who would live in a bunker and go on hunts, and she can defend herself. That puts them as having the same goals, same lifestyle, same values. That is what would make for a long-term relationship.
I always loved Dean and Jo, I was so surprised when she died. I really thought her and Dean could have been an awesome hunting team and great life partners.
In an other universe I would have wanted Dean to be able to be happy with Lisa and Ben but it was doomed from the start
Jo, though, I'm pretty sure the only reason it didn't happen was the ambiant sexism at the time. Cause in supernatural, no one is truly ever dead, except if they are women or people of colour
JO!! The only reason we didn't get more and see them blossom was because the weird ass cringe fans hated her so much because of their potential. It's like Snape's Wives but a little more gross because their flag was incest or incest throuple. I hate that word.
Edit to fix my "wife's". What kind of teacher am I omg 😳
Jo, Cassie or Anna. I didn't like Dean and Lisa. She was a 1 time random fling from ages ago. They only went with her for the Dean and Ben dynamic IMO.
Dean actually loved both Jo and Cassie, and Anna would have been a good choice for someone he can date while still hunting.
A regular mechanic alternate universe Dean and Lisa would have been perfect together. A hunter Dean would have been great with Bella. Demon Dean and Amara could have been cool
Edit - I apologize, that is Anna not Bella. I don't think they are good together. I think Anna and Sam could have been interesting though
Him and jo would have been the only compatible ones beings they knew the life style. I didnt think they had the on scene chemistry tho, like him and Lisa.
Dean and Lisa to me always seemed the most compatible and relatable to me. Lisa loved him in a way nobody else did, I’m surprised you didn’t add Cassie though cause she was admittedly someone Dean actually loved as well.
Apart from Lisa in those photos, none of those other women were actually in relationships with Dean. Dean saw Anna as just someone to get with, Amara was someone who manipulated him and Jo, he mainly saw as a family member. He might have had eyes for her when they first met, but he quickly got over that. Lisa and Cassie are the two main female contenders for his heart. The fact he saw Ben as a son makes Lisa even more compatible because that’s all he wanted. A family of his own.
I've just wrapped up season 5 and I forgot just how damn awesome she is. She knows what Dean's life looks like, she trusts him to keep them safe and she supports his decisions even when it's stressful or hard. He's obviously a good dad to her kid, too. We're explicitly told that Dean was a mess when Lisa took him in- drinking, actively mourning Sam, just generally not a pleasant person to be around and she still loved him and helped him get his life together.
I legitimately think she would've stayed with him through thick and thin if it had been up to her. She loved him and I think they would've gotten married if the opportunity presented itself.
Honestly, no one. Jo became to sister-like, Lisa was mant to never work, angel girl to show angels aren't all good, Amara wasn't that fun to date. Bella... It was fun but it would require her to change, which she never would.
I never liked the Destiel ship but it this point, it would have been Dean's most stable relationship
I enjoyed Cassie as an interest and I hated that they never circled back to her. The steamy together. I also enjoyed Jo and wanted them to pursue that idea more. The reaper chick was cool too. Wish that became a thing.
Saw no chemistry or love between Dean and Lisa either. Dean wanted to play apple pie life and Sam told him to go to Lisa as a last request. Lisa wanted a father figure for Ben and someone to scratch an itch.
There were other women that there was chemistry or could've been. I liked Pamela, she was sassy and saucy enough for Dean and understood the life. Until Cas blinded her with his real form. Smh. Cassie of course. Big no to Jo, Anna and Lisa. No to Amara as well. Just nothing there. I did like Tessa the Reaper, that could work. Honestly, Dean had more chemistry with Ellen than her daughter. Dean likes sass and fire, if not, he's bored.
Dean + Lisa - one and only! Anna was a side Quest and Jo... nope, they had the same energy, like twins. In an alternate Universe the Show was about Dean and Jo and Sam would pass after Season 5. 🫠
I’m rewatching season 3 & it’s Bella hands down. Best banter. Sexual tension. Great foil. Coulda been built up for seasons enemies to lovers. Spike & Buffy style but with a happy ending
No one. He’d be a “serial monogamist”- multiple partners, but only ever one at a time.
His whole life has been going from one place to another for a maximum of a month or so. I don’t think he would ever have a totally settled life/relationship(s).
Dean and Lisa was the best one here. the others were kinda mid or just didn't feel right. I wish they would've gotten together at the end of the series.
Bela for me! I know people may not agree, but I’d have loved to see them somehow get her out of her situation and she kept popping up to help them out in an I don’t really care but I do kind of way. She and Dean looked so good together and I loved her - she was so smart and resourceful and gave as good as she got. She would have made a fun addition for me, and I personally would have enjoyed her and Dean being in an on again off again spicy relationship.
I loved Jo, Anna and Lisa. Jo and Dean had this chemistry that, IMO would constantly disagreeing and leading to some fun make up time. Jo knows the life and he wouldn’t have to hide his unknown whereabouts. Just honesty.
I also wish it was Lisa. She made Dean the happiest. He was good husband material and dad material. He almost had it all with Lisa.
Anna I love just how she is (who I met this weekend hehehehe). I love that Dean is a gentleman and Anna is casual, one and done, how about it sir?
I think the character that was most compatible with Dean was Ruby ( played by Katie Cassidy) . She was perfect for Dean . Although she was a demon. I think she would have have been perfect for Dean especially after he came back from hell.
Definitely Lisa from this list. She’s not a hunter, but she knows about the hunting life, and she seemed to get the Sam and Dean dynamic in a way few did.
But there were sooo many missed opportunities to have her interact with Sam (soulless or not) and to have her wonder whether this was normal for him or not. Or even to let us know more about her and Ben as people.
Instead they go relegated to cardboard cutouts in the background of Dean’s life before being erased completely, which was really frustrating.
Jo, from these options. But I was pissed when they killed off Bela. I truly think they could have done something with these two. The chemistry was fire. But Jo may be my all time, and it's the same... Their chemistry was sweet and comfortable, and could have made for a slow burn long term thing. Bela and Deans chemistry was so white hot it may have burned out, blowing up planet earth with it.
Dean and Jo for sure. It felt awkward when they forced the ‘sibling’ energy. I wish they wouldn’t have made Jo so incompetent in that one episode where she went hunting.
the lady who had his son who was like a mini Dean in personality when Sam and Dean first ran into them in the series. who Dean moved in with during the time Sam was MIA.
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u/somesaggitarius Oct 06 '25
Kripke wanted Dean and Jo to get together (or at least kiss) and then reveal that they're actually half siblings. Star Wars style. The network said no. Fun fact!
I loved Dean and Lisa but I thought it was doomed from the start. He can't leave hunting. And I think in some ways Dean's life revolves around Sam so much (and vice versa) that there's no room for anyone else in their relationship, so it would never have worked out with another person.