Relationship chart
People from home
Sam Winchester • ★ ★
Even though they're both adults, Sam will always be Sammy, Dean's baby brother. He feels as though looking after Sam is his personal responsibility and he would do anything for him, even at the cost of his own life. It doesn't help that Dean doesn't put a very high value on his own life, which leads him to feel like Sam's life is worth more than his own. In the Underworld, Sam and Dean have both been lucky enough that they have both been largely unaffected by the gods' games. Their loved ones have been taken and affected, but they have been able to work together in order to do what they do best and save people. As of right now, Sam and Dean's relationship hasn't been significantly changed by being in the Underworld.
Castiel • ★ ★
Dean trusts Cas a lot. He considers him to be a close friend and a part of his family, along with Sam and Bobby. However, recent events have kind of cracked their relationship a bit. It's not irreparable, but it's definitely making Dean doubt himself and Cas a little. He feels like he placed his faith and trust in Cas, and the favor wasn't returned.
This leads to the familiar "family trusts each other" speech and to Dean talking to Balthazar and finding out about possible future events. Which is also confusing because Cas told him to trust this other angel who was apparently killed by Cas... And Dean's angry with Castiel for what he sees as Cas hiding something and attempting to deal with it on his own instead of asking the Winchesters for help.... So. Confused and hurt, I guess. Which has the unfortunate side effect of making it more likely for him to lash out at Cas in his concern.
Anna Milton • ★ ★
At first Dean wasn't sure what to make of Anna being in the Underworld. The last time that he'd seen her, she'd been trying to kill Sam, so he was understandably leery of her. But after he realized that she seemed to have no intentions of harming his brother, Dean has warmed up to her more. This was helped by an event during which Dean became a certain bouncy tiger. They were also married during another event, with an infant, a dog, and a house. He feels a little closer to Anna because of that, but he would never actually admit it or talk about it.
Another recent event that has helped his feelings towards Anna is his discovery of how lonely she is and her fear of being alone. He visited her apartment and gave her some flowers, a puppy, and himself.
Balthazar • ★ ★ ★
Things are a little weird with Balthazar for him. Dean's not quite sure what to make of this snarky angel, but in dealing with Gabriel he's noticed that the angels who've been on earth for a decent amount of time tend to have developed facades to hide their feelings behind. Part of the reason that he picks up on this is because it's also something that he does, and he's able to recognize that trait in others.
Also, Cas told him that he could trust Balthazar and, despite Balthy being largely unknown, Dean finds that he rather likes the angel's company. Even if he can be a bit of an ass. And he does trust Balthazar, even if he can't quite explain why. There's just something about him that Dean can't quite put his finger on yet.
Crowley • ★ ★ ★
Dean isn't particularly fond of the demon on the best of days, but here (and home) there have been circumstances under which he's worked with Crowley. The demon is helpful when he wants to be, but he's still a demon. Recent information that Dean has acquired from Balthazar make him even more uncertain of the demon and his intentions. He doesn't doubt that, if it were to benefit him, Crowley wouldn't hesitate to stab any of them in the back. However, most of the other people that he knows from home seem to have accepted that the demon is in the same boat as them and are willing to work with him. Dean's still not entirely sure how he feels, but he definitely doesn't trust Crowley.
Ellen Harville • ★ ★
Although he has only known Ellen for a few years, Dean still considers her family. She's helped him out quite a bit in the past, even if he has pissed her off occasionally. He cares about what happens to her, but he also feels that she's a force to be reckoned with and is pretty sure that he's a little scared of her. He has recently discovered that Ellen makes a mean pie, and the Roadhouse that she runs in the Underworld is a familiar fixture. Dean's recent argument with Bobby has caught her attention though, and he'd been avoiding her and the Roadhouse until she asked for volunteers to help clean up a mess.
People met in the Underworld
Harry Dresden • ★ ★ ★ ★
Dean isn't sure what to make of Harry because... well. Magic. It's never meant awesome things in the past for him. Especially when the people who use it are human. Dean's spent so long hunting monsters and distancing himself from getting close to people that he often understands the motives of monsters better. They are usually very clear. Whereas people, especially someone he doesn't know are so much more unpredictable. And that makes him a little uneasy. He might feel a little better if he knew that Ellen liked him.
Harry has told Dean that he uses his magic to help people, but, well... Road to hell is paved with good intentions and all that. Because of this, Dean would like to get to know Harry a little better, and until he can be more certain of the other man, Harry is labeled as a "potential threat", although that's mostly because of his connection to magic.
Sephiroth • ★ ★
Dean still isn't entirely sure how he feels about Sephiroth. Even with an "explaination", it's a little baffling as to how this guy is friends with Cas. He thinks that Sephiroth doesn't exactly have the most awesome set of social skills and is really quiet, for the most part. He has seen Sephiroth express irritation and is pretty sure that he's been a jerk on purpose, but he has no clues on how to read the guy. Despite having talked to him a few times, Dean feels that Seph is still very much unknown. But... He is a friend of Cas' and he obviously cares about him. So that wins him points. Dean would like to get to know more about him before he makes any decisions regarding him, on way or the other.
Mal Reynolds • ★ ★ ★
Something about him seems vaguely familiar, but Dean can't quite put his finger on it. He likes Mal though and is interested in learning more about him. The guy seems like he might be useful in a fight, and could be a possible ally. Mal knew the Dean that was in the Underworld before, so that implies that he can be worked with, if it has been done in the past. Unfortunately, Dean doesn't remember it.
Jack • ★ ★ ★
She was the first person that Dean encountered when he was dropped off at the dock in the Underworld. In an attempt to catch the ferryman before he pulled away from the dock, she'd run down there, firing off a biotic attack when the boat didn't stop. In his panic, Dean shot at her, wounding her and resulting in a less than civil first encounter. He's seen her around a few times since then, and the first meeting seems to have mostly been forgiven, but Jack keeps bringing it up. Either way, Dean's not sure how he feels about these "biotics" she uses to attack.
Leonard "Bones" McCoy • ★ ★ ★ ★
Dean thinks that Bones is pretty much the best thing about the underworld. Even if he is some sort of fabrication. If he is, whomever fabricated him was good, because he's perfect. And, really, drinking with Bones? Dean is thrilled that he was able to meet him. Probably even more thrilled that Bones seems to like him and hasn't hung up on him. He is one of the few people outside of his family and people from his own world that Dean trusts and would like to consider a friend. Although he has seen the television show, Dean would love the chance to find out more about Bones' world from him. He views Bones as an ally and if he ever had a friend that needed medical attention, he's at the top of his list of people to call.
Annabeth Chase • ★ ★ ★
When Dean first started talking to Annabeth, her knowledge of Greek mythology and the phrasing that she used when talking about it caught his interest. After some prying, he was able to get her to admit that she had prior experience with some of the creatures of Greek mythology. He's pretty certain that she's somehow connected to the Greek gods, but doesn't actually have any proof of this since she was less than forthcoming on the subject. Either way, her knowledge of mythology could make her a useful ally and Dean would like to talk with her again sometime. Maybe, over time, she'll be less of a mystery.
Misaki Asou • ★ ★
It's obvious that she cares about Cas, which gives her points in Dean's book. Harry also told him to talk to her if he wanted information about the Underworld, and that's something that Dean eventually intends to do once he actually gets a second to breath. Aside from Harry and Cas though, Dean doesn't know about her relationships with anybody else that he knows, but that would probably serve to make him even more interested in getting to know her. Either way, anybody with knowledge is good for Dean, because that means less research for him.
Lúthien Tinúviel • ★ ★ ★
Their first meeting was less than ideal, since Cas was bleeding out all over the kitchen floor. But she introduced herself as a half elf from Middle Earth, and that definitely got Dean's attention. The way he sees it, if Star Trek characters can show up here, why not elves. She was also nice enough to offer to help Cas out and come over to their house in order to do so. Dean would like to talk with her again sometime when there's not a crisis going on since he would like to know more about her.
Voodoo • ★
She's one of Cas' friends. Dean doesn't really know anything else about her because he hasn't had the chance to talk with her much at all. He doesn't even know what her name is. But she does seem to be concerned for Cas' wellbeing, and he's interested in talking to her or finding out more about her.
Christine Chapel • ★
Having met her during the mirror injuries event, Dean knows next to nothing about Christine. The only time that he's ever spoken to her, she mistook him for the other Dean. But she was also suffering serious injuries at the time, so he didn't correct her. From looking through archived conversations, he knows that she's Bones' nurse, so he assumes that she's Christine Chapel, but he would like to know more about her.
People who are gone
Bobby Singer • ★ ★
Since Dean was younger, Bobby has been a constant in his life. And since John Winchester's death, he's been like a father to both Dean and Sam. Whenever either of the boys is in trouble, Bobby is often the first person that they'll turn to. Dean looks to him for advice on both business and personal matters.
However, as a result of asking Bobby's opinion, Dean and Bobby are currently not speaking to each other. Dean wanted Bobby's opinion of things concerning Cas and their conversation quickly headed downhill, with neither party really listening to what the other was saying. Dean feels bad about it, but has yet to suck it up and just apologize.
Dean Winchester • ★ ★
As if having another Dean running around wasn't bad enough, this guy is also a vampire. Dean really isn't sure how he feels about this guy. They might be able to work together and he seems to care about Dean's family, but he's still a vampire. And if that wasn't bad enough, he feeds on humans. Dean's definitely going to be keeping an eye on him. He doesn't want somebody running around and doing bad things while they're wearing his face.
Gabriel • ★ ★
When Gabriel first arrived in the Underworld, Dean wasn't entirely sure what to make of it. In their first conversation, he reveals to Gabriel that he knows the archangel dies, but he was able to save Kali and the Winchesters. Shortly after that, Gabriel insisted that Dean come and drink with him as payback for telling him that he's dead. Despite having had less than pleasant run ins with the archangel in the past, Dean finds that he actually doesn't mind the guy. And even if he had put them through Hell, he's not actually that bad. Especially as far as angels go. Dean enjoys spending time at Gabriel's apartment, usually drinking or playing games with the systems that the archangel has conjured. He has an open invitation to the apartment and has, on the rare occasion, entertained someone there since the array of booze is rather impressive. Dean considers the archangel to be something of a friend, although he's not entirely certain if he should trust him. He's pretty certain that Gabriel would come through in a pinch though.
Kurt Wagner • ★ ★ ★ ★
He's the first person that Dean has come across in the Underworld who's left and come back without having forgotten his time spent in the Underworld. Dean isn't sure what to make of this since all of the people that he's heard of, including Sam and himself, have forgotten their previous time in this place. Kurt is also a source of interest since he's one of the X-Men, Nightcrawler. Dean would like to learn more about him and maybe have a drink or two sometime.
Claire Danvers • ★ ★ ★
They started talking after the other Dean showed up and the conversation eventually turned towards vampires and Claire's involvement with the Morganville vampires. Dean thinks that she's in a really crappy position for someone so young and that she should have the chance to live a normal life. What she's told him about Morganville has made Dean determine that if he ever finds this city, he's going to lay the vampires to waste. After discussing vampires, he mentioned that there were other things out there that would pray on humans and he agreed to teach Claire about them so that she could protect herself. Although he doesn't know her very well, he sees her as a kid who's in danger and being used by vampires. He would help her in any way that he could.
Family/Loves ★ • Trusts/Friend ★ • Interesting ★ • Possible Ally ★ • Acquaintances ★
Dislike ★ • Possible Threat? ★ • Dangerous ★
People that Dean knows as fictional and is a fan of ★