Hi! As with literally any relationship in Star Wars, there are complications and things that are difficult, you could make a case that there’s unhealthy aspects to every single relationship in the franchise! You can take any two characters that have any kind of significant relationship, especially with Anakin, and point out aspects that are Not Great about it, because that’s how SW is and that’s how Anakin is! Literally every relationship he has, from Obi-Wan to Padme to his mother to Ahsoka to Rex, all have aspects that we can deem to be unhealthy.
Take how George Lucas describes his relationship with Padme and Shmi: “But he has become attached to his mother and he will become attached to Padme and these things are, for a Jedi, who needs to have a clear mind and not be influenced by threats to their attachments, a dangerous situation. And it feeds into fear of losing things, which feeds into greed, wanting to keep things, wanting to keep his possessions and things that he should be letting go of. His fear of losing her turns to anger at losing her, which ultimately turns to revenge in wiping out the village. The scene with the Tusken Raiders is the first scene that ultimately takes him on the road to the dark side. I mean he’s been prepping for this, but that’s the one where he’s sort of doing something that is completely inappropriate.“ –Attack of the Clones commentary
“And of course that’s the problem with Anakin ultimately. You’re allowed to love people, but you’re not allowed to possess them. And what he did is he fell in love and married her and then became jealous. Then he saw in his visions that she was going to die, and he couldn’t stand losing her. So in order to not lose her, he made a pact with the devil to be able to become all-powerful. When he did that, she didn’t want to have anything to do with him anymore, so he lost her.” –The Clone Wars writers meeting
It’s not exactly hard to see the unhealthy aspects of those relationships, but that doesn’t mean they weren’t real or that they weren’t good, too! Now here’s how George Lucas describes Obi-Wan and Anakin’s introduction in Attack of the Clones, which is arguably where the movies give us the foundation of what we know about these characters:
“[The] scene was needed in the elevator leading up to the Senate apartment, to more firmly establish the friendly, affectionate relationship between Obi-Wan and Anakin. ‘In that first cut,’ Lucas explained, ‘the student-mentor relationship between Obi-Wan and Anakin was pretty rough right away, which got everything off to a bad start. Then, throughout the rest of the film, Obi-Wan is tough on Anakin, and Anakin is upset with how Obi-Wan treats him. After seeing the movie, I realized that we needed to soften their relationship a little bit, so the audience would see that they are actually friends. So I added this new scene in the elevator to establish that they actually like each other. All the way through the movie, I had to find a delicate balance between their affection for each other and the tension that is always between them.’“ –Mythmaking: Behind the Scenes of Star Wars: Episode 2: Attack of the Clones [x]
It’s not that Obi-Wan and Anakin’s relationship isn’t difficult, of course it is. But that’s because that’s how relationships work, especially when you’re in the middle of difficult circumstances, as all the characters in Star Wars are. But that’s not the same as not being good for each other!
On a fundamental storytelling level, if Obi-Wan and Anakin weren’t friends, if they didn’t care, like, and even love each other, then why would the final prequels movie center the big climax around them? It wouldn’t tug at our hearts, it wouldn’t hurt us, if we weren’t watched a tragedy, that these characters were falling apart, that in George Lucas’ words, is Anakin forcing his friends to act against him because of what he’s done.
This is a moment that breaks our heart because they loved each other.
Even the writing by the choreographer of Revenge of the Sith was specifically designed around the idea that they were important to each other, loved each other, and that Obi-Wan was giving Anakin every possible chance:
The fight is literally written to show us that Obi-Wan is still trying to get Anakin back, because he loves Anakin so much.
Their meeting again on the Death Star wouldn’t be this big, epic thing if we weren’t witnessing two people who loved each other and were once upon a time good together, now turned dark and twisted.
Their final ending, seeing them together again in the Force, hearing George Lucas be heard saying that Anakin “had help from the other side”, wouldn’t be nearly as powerful if it weren’t a return to when they were good together, seeing Anakin standing by Obi-Wan and Yoda is powerful because it’s a return to the good person, the good friend he was, once upon a time. The man that Obi-Wan remembers, when he’s talking to Luke about him in A New Hope.
And it’s not hard to find evidence of that in the rest of the movies and the TV series:
Anakin loses his shit because he thinks Obi-Wan is dead, he doesn’t speak for days and is wrestling very hard with the dark side, would have killed Rako Hardeen if not for Obi-Wan’s memory, that Obi-Wan wouldn’t have wanted him to kill someone, and that’s the only reason he doesn’t.
Palpatine wouldn’t be having such a field day with manipulating Anakin with this–telling him that Hardeen was last seen on Nal Hutta, specifically to go get Anakin riled up and stirring up those intense feelings inside of him, because Palpatine had to drive a wedge in between Obi-Wan and Anakin–if Anakin’s feelings about Obi-Wan weren’t important, just like how Palpatine used Anakin’s feelings for Padme to twist him around, used Anakin’s feelings for Ahsoka to twist him around.
We also see that Obi-Wan cares very much about Anakin in turn, too, that he absolutely loves him. Reserved people don’t always have to vomit their feelings everywhere to express themselves in the “right” way, but we very clearly see Obi-Wan express these things anyway:
When he’s worried about how Anakin’s sleeping, he takes time out of their duty to ask how he’s doing, and the expression he wears is very genuinely concerned, that is the face of someone who very much cares and is asking because they’re there for support.
Obi-Wan’s advice, from what Anakin tells him (there’s no mention of these dreams being dangerous, we’re not given any indication that Anakin has visions/that this is a vision) is reasonable. (And if we’re going to give Obi-Wan shit about this, we have to give double shit to Padme for saying, “It’s just a dream.” in ROTS despite that she knows exactly what Anakin did because of his dreams in AOTC.)
Also in this scene, in addition to the moments in the elevator (where Obi-Wan deliberately is teasing Anakin because Anakin was spiraling emotionally, showing that he’s actually really good at jolting Anakin out of a panicked state), Obi-Wan sees Anakin start to spiral again when he says Padme didn’t seem to care that he was back, so Obi-Wan says to mind his feelings (GOOD ADVICE) but also cheers him up with, “But she was pleased to see us.” because he’s very much watching out for Anakin’s mood.
The entire point of this conversation in the Clovis arc of s5 is that Obi-Wan senses there’s a lot going on with Anakin and he makes himself available to talk, to tell Anakin that he needs to get a grip on himself, which is what a good friend does. They don’t just blindly support you, they instead look out for you, and when you need to hear something difficult, they tell you, in a kind and supportive way, you need to get your shit together. Because blindly enabling Anakin is a really bad idea, given what we know he’s capable of.
This is why, yes, they’re at odds in AOTC, because Anakin is overstepping his bounds and promising things the Jedi can’t reasonably be expected to deliver on, he’s being bratty and so of course Obi-Wan’s reaction is going to be, “We will TALK ABOUT THIS in the CAR.” at him.
In contrast, just a few minutes later in the movie, Obi-Wan’s cheering him up again, then later that night asking after him in concern, then they go on the speeder chase together and we get a visual demonstration of how well they actually do work together, that they both clearly enjoy the bickering and bantering.
And there’s more good moments, too!
Obi-Wan easily and warmly smiles at Anakin in ROTS, praises him and tells him how proud he is of him, the whole point of including this scene is like the elevator one, to show us that they care about each other, they get along, they work well together, they’re good for each other when they’re around.
It’s when Obi-Wan’s not there that Anakin does his worst things–when Obi-Wan is on Geonosis and Anakin on Tatooine, he murders the Sand People and their children. When Obi-Wan is on Utapau and Anakin on Coruscant, that’s when Anakin goes off the deep end.
Obi-Wan is an incredibly valuable counterweight to Anakin’s teetering towards disaster and, without him there, that’s when Anakin really starts to fall apart.
Also, by the rules of how the psychic powers of Star Wars seem to work, you have to know someone really well to really feel their presence in the Force, that’s why (as Dave Filoni explained in an interview) Kanan can’t really be sure that it’s Luminara at Stygion Prime, because he never really knew her. In contrast, he said, when Anakin felt Obi-Wan’s presence on the Death Star, it was like a battering ram, because they had been so familiar to each other.
We see that reflected in small ways with how they pick up on each other’s psychic moods:
Or moments when they’re physically affectionate with each other in small, but very telling ways!
These are all the more significant for the casual ease with how they touch each other:
And we see that Obi-Wan is actually really good with Anakin, as a teacher:
When a young Anakin thinks that Obi-Wan doesn’t want him around (a pretty normal thing in a story like this), he explodes about it and Obi-Wan talks very openly and genuinely with him, about subjects that are pretty sensitive.
He explains that he felt like he couldn’t help even a full grown adult, when Qui-Gon was killed by Maul, so how could he protect a Padawan that was entrusted to him? He felt like Anakin would have preferred having Qui-Gon, which he explains without ever accusing Anakin of behaving badly, he never lays any of this on his student.
He’s not just being kind, he’s emotionally available to Anakin, balanced with showing that one doesn’t have to be perfect even as an adult and yet still have their shit together.
And this works beautifully, Anakin lights up and understands what was going on, they solved the problem and work well together. (This is the whole idea behind how they became The Team, you don’t get that level of complementing each other if you’re not good together!)
This is important, because Anakin really, really needs someone who is extra considerate of him, because he’s not great at getting outside of his own head sometimes. Oh, he has a wonderful heart and he cares very much about others, but sometimes it’s hard for him to parse what others actually mean versus what he thinks they mean, because his fears and anxiety tend to chew on the wires in his mind.
Obi-Wan is a great teacher for him in this because he’s doing as much as is possible to work around that, to balance that Anakin needs a little extra help with the consideration versus that Anakin needs to learn to start trusting others.
We see that this kind of dynamic continues into when Anakin has been Knighted and Obi-Wan still seeks him out to offer an ear to talk, to praise him when Anakin’s doing well:
There are no easy answers in this war, nobody has them, otherwise none of them would be where they are. But Anakin feels intensely about the events happening in this issue, he has these intensely held beliefs, and Obi-Wan smiles and him and praises him for it, supports him in it. Anakin becomes more focused and confident in himself because Obi-Wan helped nudge him in the right direction.
We see that Obi-Wan is a good teacher for Anakin and a good friend. I think there could be some debate about whether Obi-Wan should have been less his friend and more his mentor, but I often wind up circling back to how I don’t think that Anakin would have really listened to anything less than the careful line that Obi-Wan walked.
I keep thinking about: How would Anakin have reacted in a situation like this?
Where Qui-Gon seems to be shunting Obi-Wan to the side, despite just earlier in the movie he said Obi-Wan still had much to learn, but now he’s saying that Obi-Wan’s ready, because he wants to take Anakin as his Padawan?
Obi-Wan understands this and gets over the sting, he knows that Qui-Gon cared about him, he’s able to get out of his own head enough to recognize that even if this kind of hurt, that Qui-Gon didn’t do it because he didn’t care. Can you imagine if Anakin had been in this position? If his Master had been so willing to set him aside like this and felt that he should get out of his own head long enough to see that it wasn’t meant as a slight against him?
This is why I will always argue that Obi-Wan was the best choice for Anakin, because he stayed dedicated to Anakin even after his Knighting, because he was constantly asking after him and demonstrating care for him, while also working Anakin towards becoming more balanced. We see, in stories like the Age of the Republic comics or in the early episodes of The Clone Wars, where Palpatine has less direct influence/when Anakin goes to see him less, that they tend to work things out pretty well, that Anakin rises to the occasion, like Obi-Wan knows he can.
Maybe another Jedi would have been able to achieve that same balance, I certainly would have enjoyed seeing Yoda attempt it or maybe Mace Windu attempt it (their banter is delightful and clearly Anakin gets a charge out of it in TCW, he’s practically laughing as they “argue” in the Boba episodes), but certainly Obi-Wan was a great complement to Anakin and Anakin was a great complement to Obi-Wan.
And, ultimately, Anakin knows that Obi-Wan loved him, he knows that even after EVERYTHING, he could still have gone to Obi-Wan for help and Obi-Wan would have listened. Like when he has his vision in Darth Vader: Dark Lord of the Sith:
This is entirely Vader’s vision, he recognizes that this is true, that Obi-Wan would listen to him, would turn off his saber if Anakin asked him for help.
These are two people who were driven apart and it hurts because they were good for each other and they liked each other so much. Of course they had their issues, that’s true of every single relationship in Star Wars, it wouldn’t be an interesting story if they didn’t! Obi-Wan believes a little too much in Anakin, Anakin doesn’t trust Obi-Wan nearly enough, etc.
Mileages may vary, I’m not here to change your mind if you’ve seen all this, read all the comics and books and played the games, and still felt like they were never really friends, then that’s as valid an interpretation for you as all of the above is for me. But this is why I absolutely do think they were great together, that the story showed them as great friends, as two people who were monumentally important to each other, to the point that even when they’d spent 20 years apart, they still revolved around each other. That Vader wouldn’t shut up about Obi-Wan [x][x] and that even Obi-Wan’s death was still about Anakin, just as much as Luke [x].
And at the end of the day, man, these two clearly just liked the hell out of each other: