Hi! There are some excellent Obi-Wan and/or Ahsoka fics in the fandom! Not all of them will necessarily feature a ton of interaction between the characters, but you will have a ton of reading material if you just enjoy reading about the characters! I have a long archive of fic recs here, where any given list will give you at least something to check out for both characters! But if you want to hit up some of the Must Read Firsts, LET ME HELP WITH THAT.
OBI-WAN & AHSOKA:
A Future in Crisis by WolfMarauder is a fic where Ahsoka has a vision of the terrible future to come, so she returns to the Jedi, works through her feelings and starts working on saving the rest of the galaxy. At it’s heart it’s very much an Ahsoka story, about her figuring herself and her relationships out, as much as it is about being a fix-it fic. There’s such a warmth and charm to this fic that it’s like being in a warm bath and relaxing into it. There’s very much a plot going on here, a complicated relationship with Anakin because of Everything, but it’s balanced with something that feels really, really good to read.
The Journey of the Lights by Pandora151 is a fic that I got sucked into and couldn’t stop until I’d finished the first one, because it’s a Canon Divergent AU where things go just a little differently, things snowball, and it’s painful but so good and ultimately I think things end up in a better place. Another great fic if you want plot, super satisfying confrontations that have been building for ages, and a progression towards things changing, in a way that’s often not easy, but works.
Chosen, not assigned by Lysore is one where, ultimately, Anakin and Ahsoka’s relationship became absolutely incredible and Yoda was right about how good they were for each other, but what would it have been like if things were nudged a little to the left and she’d been chosen by Obi-Wan instead? That she’d felt directly wanted from the beginning instead? And it’s a lovely piece that explores that!
Tano and Kenobi by FireflyFish is a time travel fic with Ahsoka going back to the past, taking a young Obi-Wan as her Padawan instead. The fic is admittedly pretty hard on Qui-Gon, as well as their dynamic is different here because this is an Obi-Wan who is not yet an adult, but Ahsoka is, so they’re very changed from how they were before. But it’s two and a half novels worth of plot and development and fun and angst and action! It’s an incredibly written fic and does so much to really build up what it’s going for and really earns the massive changes it’s making. Fishy is an amazing writer and I love the wide span of dynamics she gets into this story, so many different relationships, even as Ahsoka & Obi-Wan is the central one! PLUS TIME TRAVEL FIX IT FIC, YESSS.
Declarations by Nny11 is a series of scenes exploring Obi-Wan and Ahsoka’s relationship and I always like anything I read by this author. I haven’t finished this one yet, but I’ve enjoyed what I’ve read of Close But No Cigar (Ahsoka-centric fic where the timeline is changed a little and she’s Yoda’s Padawan instead and it spirals out from there) and Let’s Try This Again with a time-traveling Ahsoka in toddler form (so it’s more Obi-Wan & Anakin & Ahsoka) is probably my favorite of the author’s!
Waiting and Learning by otherhawk is a lovely piece for Obi-Wan & Ahsoka that’s balanced between hilarious antics and the more painful aspects of what it means to be a psychic space wizard who wants to help people. There’s such kindness here, even as it aches, in a way that’s very deftly done.
The Only Way Through by victoria_p (musesfool) is a shorter piece, but has this really well done balance between the familiarity between them and yet how they’ve both grown so much older, during Obi-Wan’s time on Tatooine. There’s so much pain in the background, but that doesn’t mean there’s not still moments and sparks of light to be found, which is perfect for them.
Under a purple sun… by Perspicacia is Obi-Wan helping Ahsoka with her homework and it’s short but so lovely, it does a fantastic job with their dynamic and weaves in a few really nice details about Jedi philosophy that are hinted at, and is just warm and charming exactly as it should be.
The Ryloth Excursion by Icarus_is_flying is one I love, where Obi-Wan and Ahsoka are on Ryloth, where she asks some questions that don’t have easy answers (but aren’t awful questions, either), and Obi-Wan’s guidance as her grandmaster is absolutely wonderful.
Knight-Errant by zinjadu is about three novels worth of fic, which doesn’t have a lot of them interacting directly, but Ahsoka is probably the most central character and Obi-Wan has a lot of scenes in it, plus SO MUCH PLOT. I’ve read about a third of the series so far and it’s incredibly engaging, where Ahsoka’s choice to stay with the Jedi helps shift things a little to the left, then a little more to the left, and suddenly everything is snowballing, all the same pieces we’re familiar with are in different places and maybe they might have a chance! It is Rex/Ahsoka eventually, but it’s a very slow burn to get there and it’s not the only relationship that’s important to them. It’s an Ahsoka piece and an ensemble piece and a fix it piece and a huge sprawling plot epic, and I’m loving it a lot.
When Darkness Seems to Hide This Place by IllyanaA is another one where Obi-Wan and Ahsoka don’t interact directly a lot, but they’re both very present in the story and get some really excellent scenes. The Jedi manage to scrape a few more people together, Anakin doesn’t turn on them, so they’re still in the middle of a galaxy that’s hunting them down, but now they might be able to mount a fighting chance sooner than before. The Obi-Wan & Anakin scenes are stellar, Ahsoka gets her own subplot, and it’s a lot of really excellent plot as they figure out how to rebuild in this new Empire.
Echoes of Mortis by orphan_account is more Obi-Wan & Anakin + Anakin & Ahsoka, but both are well done here, and the plot is excellent. It’s marked as incomplete, but I would say that it reaches a place of good resolution and I felt satisfied by the ending! In a Canon Divergent AU, where Anakin remembers everything that happened on Mortis, things go a little differently. Which is very, very much not the same as easier, but it does lead to better places, even when everything is painful and ouchy in the best ways. A lot of angst, but the kind I eat up with a spoon, it was so good.
Obi-Wan and the Terrible Horrible No Good Very Bad (Life) Day by orphan_account is charming and adorable, that Obi-Wan’s life day is beset upon him by the people who care about him and it’s just an absolute JOY to read.
OBI-WAN KENOBI:
Fire and Ice by Yesac is the one fic I always, always come back to, the one I keep rereading and the one I would put at the very top of my list of fics that I think really wrote Obi-Wan brilliantly. Oh, sure, there’s some stuff I disagree with, a few brief bits of the Jedi weren’t allowed to love or the like, but they’re extremely minor in a fic that shows otherwise. This is a fic where Anakin won the duel on Mustafar and kept Obi-Wan and Padme hostage both, unable to let either of them go. This is an Anakin who has this tremendous power but no core of self-understanding, so he’s legitimately unstable, you feel how fragile and cracked he is. In comparison, Obi-Wan is steady and unbreakable, even when he’s entirely human. This fic gets the balance of that, of who Obi-Wan is and how he relates to Anakin Skywalker, in that way that I can’t even be coherent about because it’s so well done. Yeah, I’m probably overhyping it, but this one is just my fucking jam.
starbird by imaginarykat is the other fic that I always come back to as a fic that really gets Obi-Wan Kenobi, the mix of flirtation and humor and seriousness and insight and how he’s both direct and wily at the same time, that Anakin’s just kind of spun around by him when Obi-Wan really focuses on him. Yeah, wicked thing is the more popular one by this author (for good reason!) but I always love starbird for the one I can point to as a more canon-friendly version of Why I Love Obi-Wan Kenobi So Much. (Obikin.)
The Dark Path Lit by Sun and Stars by A_Delicate_Fury is a brilliantly done time travel fic where Obi-Wan, Luke, Leia, and Han end up back in the past and even in just the smallest of gestures, this fic gets Obi-Wan, all the more so because it’s balancing a character who is both the General Kenobi of the war and the Old Ben of Tatooine as they suddenly find themselves occupying the same mental space!
Cataclasm by dendral is another excellent fic that does right by Obi-Wan’s character, where he gets a vision of something and decides he needs to take another path in this terrible war they’ve all been dragged into. He takes Waxer along for the ride, going around the galaxy where the Force leads them, getting into batshit Jedi scrapes, trying his best to save people, and it’s this really beautifully done action fic, buddy fic, and examination of what the war has done to the Jedi and why it’s such a tragedy.
The Living Force; Parables for Padawans by glorious_clio is a beautiful piece for both Obi-Wan as a character and for a story-within-a-story about what a Jedi fairy tale would be like. It does such a beautiful job of telling interesting stories, the kind that would be used to make generations of Jedi think and turn them over and find meaning in them, while also illustrating the deeper meaning of the lines that make up their most famous meditation mantra. Stunning work.
Supreme Chancellor Obi-Wan Kenobi by stonefreeak is an ensemble piece, but it’s centered around Obi-Wan and is really great if you’re a fan of his character, where he has pretty much The Most Exasperating Day Ever and winds up elected as Supreme Chancellor of the Republic and then everything starts slowly inching towards the left, now that the Jedi and the good people of the Senate have some actual breathing room. It’s about what might have been possible in a galaxy with a little more good faith to go around, as well as a great look at Obi-Wan’s relationships with various characters. An absolute scream to read, but also a really delightful plot.
Remedial Jedi Theology by MarbleGlove is a fic that is very much based on Legends, rather than on canon/George Lucas’ Star Wars, so you have to roll with that when you pick this fic up (which I find useful to note mainly in the context of those who find my recs useful/want a heads up, never really as a value judgement), but what you’ll get is an incredibly thoughtful, warm-hearted fic that I found to be incredibly engaging and charming. The entire fic is about Obi-Wan trying to figure out just how to train Anakin and how to fit him into the bigger structure of the Jedi Order, how to adjust himself and that structure to better fit his new Padawan and the other Jedi learners, but in a way that’s also about understanding why they’re set up the way they are, about how deeply caring they are, and how thoughtful they are. It’s a good faith look at the Jedi and a great look at Obi-Wan’s character.
Reprise by Elfpen is another fic that I’m only a third of the way through so far (I’ve been hoarding it for awhile) but it has some absolutely stellar Obi-Wan characterization, who is someone that’s really Seen Some Shit, who feels kind of lost sometimes, who feels things very deeply, but who also has a kind of strength that allows him to continue rising above. It’s not that he’s untouchable by mortal feelings, but that he’s used to understanding himself, acknowledging himself, and working through what needs to be worked through. Combine this with some really stellar writing for Qui-Gon, for Obi-Wan’s younger self, for the other Jedi around him, for the plot, and it really is one of the best fics in the fandom.
The Exchange by MissLearn is one of those that I absolutely fell in love with, where Obi-Wan and Anakin exchange places with their TPM and pre-ROTS selves, which leads to a lot of shit hitting the fan in a way that is forcing things to a head a little earlier, so they can deal with it in a way that they couldn’t in canon. It’s a great look at their relationship, both the beginning of it and the established one, as well as the glee of having them in different eras and seeing how they react/how the people around them react!
The Hand Dealt by not paranoid enough is another favorite, where it’s about a simple twist that changes so much–instead of Qui-Gon going to Tatooine, it’s Obi-Wan who meets Anakin first, and that shifts everything to the left just enough that everything is so recognizable and yet different. It’s an engrossing read as things happen differently, some good and some bad, and it’s an amazing read.
Though Lovers Be Lost by panharmonium is a shorter but absolutely fantastic look at Obi-Wan’s character. I love all of pan’s fic, The Mathematics of Repair and Take My Waking Slow are both great looks at Obi-Wan and Anakin’s early days, but I think the first one is a great starting place for a fan of his character, it’s beautifully written.
After the Pillars Come Down by Virgo827 is a fic that deserves so much love because it’s one of those that, aside from the acknowledgement of Obikin, it could have fit right into an episode of The Clone Wars. It does a lovely job of Obi-Wan being level-headed and focused, but that something about Anakin makes him lose his mind a little, that Anakin is that one person that he finds it difficult to remain calm about, which speaks to how blind he was towards Anakin’s faults, because he loved that guy so much. It also has a real, genuine plot that’s a fantastic read, it has amazing Anakin moments, and it was an incredibly satisfying read.
Equinox by lilyconrad is a fic I’ll never not be biased about, because it was written for me and tailored to my wants, but I genuinely hold this up as one of the best examinations of Obi-Wan’s character and his relationship with Anakin, as it moves from one of friends to one of lovers. It’s a look at what having Sith versions of themselves means for parallels and contrasts alike, what that forces Anakin and Obi-Wan to understand about themselves and their feelings towards the other. And it has a fantastic plot! Every chapter of this fic was one I wrote like three paragraphs of a rec for because it had such thought and care put into it, so it’s probably always and forever my #1 Obikin fic.
Upfall by bell (belldreams) is a stellar Obikin read for both Obi-Wan and Anakin’s characters, where so much thought has gone into each chapter, as well as some incredibly building tension and breaking. This is a fic that is very, very aware of Anakin’s character arc in canon and the things he does there, as well as it’s an incredible look at Obi-Wan trying to balance his own boundaries, that he’s allowed to have his own internal world that’s not just about Anakin, versus that Anakin is the one he’ll always choose, even when he’s being a shit. Seed is another one I love (Anakin contracts a virus that means he needs to give Obi-Wan blowjobs and then, oh, no, feelings happen) that does an amazing job of looking at the characters and digging into the issues they have. bell really gets the both of them and these are incredible reads for them.
Pas de Deux by Ghost_Owl is a lovely look at Obi-Wan and Anakin and Ahsoka. Well, it’s primarily Obi-Wan and Anakin, but it’s about Anakin’s relationship with Ahsoka in the background as well, shown through the lens of Obi-Wan & Anakin. I love this one because it’s about how difficult it is to balance that Obi-Wan was his Master, but is now his friend, that Anakin bends over backwards to lash out sometimes, instead of listening, instead of still accepting Obi-Wan’s guidance, but that they can muddle their way through to something good again. And its characterization is lovely, too!
AHSOKA TANO:
What We’ve Become by Vinyarie is probably my favorite Ahsoka fic, where the first one is an absolutely gorgeous look at her getting trapped on Malachor with Vader, where they have to depend on each other to live, which gives them time to breathe and then argue some more. The characterization for her is spot-on, where she is a grown woman who is settled in her own skin, that she still feels deeply but she has a hell of a grip on herself. That she may not be a Jedi anymore, but she still carries their teachings in her heart, and that strength of her sense of self is beautifully shown. The second fic is one where she visits Obi-Wan on Tatooine and I loved the conversation they have, as well as the digging into her character even further and what she really wants from here.
time to change the road you’re on by wreckageofstars is time travel fic with Ahsoka and is another absolutely stellar look at her character, that it’s partly about her relationships with others (especially Anakin) but is also about her coming to understanding about everything around her and even herself somewhat. This is an older Ahsoka, the one who has settled into her own skin more, and it’s a beautiful look at her AND a time travel plot!
Old Sins Cast Long Shadows by zarabithia is an AU where Anakin died in the fight against Palpatine and the galaxy has to continue on without him. Ahsoka takes up the job of protecting Padme on Tatooine, giving her time to heal from everything that’s happened, as well as Obi-Wan eventually joins them, and it’s a lovely look at Ahsoka’s character and the dull ache of Anakin being dead in this universe, but knowing that things are so, so much better here.
Strange Meetings by gilestel is a beautiful post-Return of the Jedi scene between Ahsoka and Luke, where they don’t have much time to talk, but the potential of it and promise of it and just the immediacy of the moment are all lovely.
memories like ashes at our feet by ambiguously is another shorter fic but a fantastic one where Ahsoka is stranded with an amnesiac Vader and has to walk the line between that this is something of her Anakin back, but also that this is still Darth Vader and he could regain his memories at any point. It’s aching and hopeful in all the right places.
The Season’s Rain by Bythoseburningembers is an absolute scream of a fic, where Lux and Steela and Saw join Ahsoka in the Jedi camp, where they get to see them in a more relaxed state and they are all a bunch of absolute CHILDREN. It’s one of those fics that could have been bordering on parody, but the strength of the writing and the charm of the characterizations instead makes it a fantastic look at the Jedi and clones being entirely relatable, being family to each other, and I love everyone in this, including Obi-Wan and Ahsoka.
The Cave by Ria Talla (ronia) is one where absolutely fell in love with this gorgeous fic because it pulls off a dreamy mishmash of imagery and slipping from one memory/moment to the next beautifully, it does a gorgeous job of making Ahsoka feel unstuck in time after the events on Malachor. Which is wonderful in and of itself, but it lends such a great weight to the cost of traveling through the World Between Worlds as she did, that there’s a reason that it’s not a thing to use lightly, and it’s not punishment, but consequence all the same, as the fic says. It has some really great characterization for her, too.
