1 - 20 of 32 Works in Insecure Anakin Skywalker
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Listing Works
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Why Don't You Write Me by tatooinelizard
Fandoms: Star Wars - All Media Types, Star Wars: The Clone Wars (2008) - All Media Types
07 Sep 2025
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Summary
While Anakin is stationed on a jungle planet carrying out yet another campaign against the Separatists, Obi-Wan suddenly stops responding to his messages. Anakin is definitely not freaking out about it.
Series
- Part 2 of Softer than the Rain
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Summary
"No one wanted me, except for Qui-Gon. But he died. And suddenly the Jedi were stuck with me." Anakin paused, hesitating. "Obi-Wan was stuck with me."
Nausea rose in Obi-Wan's throat. He had failed Anakin, he realized. No padawan should feel like his Master didn't want him.
OR: Anakin tells Ahsoka about his past and his early years as a padawan. Obi-Wan happens to overhear and realizes that he has fucked some things up.
Series
- Part 4 of Drabbles/Short fics
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A Mandalorian father (or: Family is more than blood... but blood will always mean something) by Hilimi
Fandoms: Star Wars - All Media Types, Star Wars Prequel Trilogy
17 Aug 2025
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Obi-Wan had managed to keep his deepest reaction to himself during the guided tour of Kamino, but now he was absolutely certain. It was the same man. It was him.
The man who had impregnated him during his wonderful Mandalorian mission.
Cal's father.And now millions and millions of men wore his face.
Series
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Grocery Shopping Is So Romantic by tatooinelizard
Fandoms: Star Wars - All Media Types, Star Wars Prequel Trilogy
04 Aug 2025
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“Anakin, I love you, but don’t you think this parking spot is a bit… tight?”
“O ye of little faith,” responded Anakin, who started pulling the van up to the parked cars in front of them, then shifted the car into reverse.
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The Jedi also have soulmates (Obi-Wan says no) by Hilimi
Fandoms: Star Wars - All Media Types, Star Wars Prequel Trilogy, Star Wars: The Clone Wars (2008) - All Media Types
21 Apr 2025
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Obi-Wan thought he was done with the Jedi when he had returned to his parents' home after leaving the Jedi Order, when all his hopes of becoming a Jedi consular, and more specifically a Jedi diplomat, had been dashed.
Of course, he had met some of them again, but that was nothing more than small talk from a Deep Core Senator to someone advising a peaceful approach to what would probably be tough negotiations.
Twenty years had passed, he had made a life for himself, a life he enjoyed and was proud of. And now what, they expected him to put his life on hold to be the caring Omega of their Hero With no Fear? Of the one his last hope of becoming a Jedi had chosen when he himself had not been deemed good enough?
Die.
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Sugar hearts by Hilimi
Fandoms: Star Wars - All Media Types, Star Wars Prequel Trilogy, Star Wars: The Clone Wars (2008) - All Media Types
11 Apr 2025
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Summary
Of course, Anakin would never pretend that dating a former Sugar Baby was an easy thing for Rex's family to understand and accept, but... yeah, he was expecting a bit better from them, especially for a first meeting.
Therapy had not taught him how to deal with his man's family asking him to break up with him because he was not good enough.
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Spot me? by WhiteRequiem
Fandoms: Star Wars - All Media Types, Star Wars: The Clone Wars (2008) - All Media Types, Star Wars Prequel Trilogy
03 Apr 2025
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Quinlan and Anakin work out together
Quinlan had seen Anakin shirtless in the training rooms between missions before. They hadn’t interacted much back then, but Quinlan had noticed how in shape Anakin was. He'd been thin with hard packed muscle, not an ounce of fat on his body and the endurance to spar for hours.
Quinlan immediately felt bad, he’d just wanted a fun workout buddy, he hadn’t meant to make Anakin feel bad about himself.
Series
- Part 10 of Summer Paradise
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Tell Me All Your Sweet, Sweet Little Lies by Legogirl22
Fandoms: Star Wars - All Media Types, Star Wars Prequel Trilogy
14 Feb 2025
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Summary
Everything is over. Qui-Gon has been burned, Obi-wan has taken him as his padawan, and Anakin is free. Now what?
Series
- Part 2 of Weekly Prompt Challenge: Year One
- Part 1 of Anakin's Training Years
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Too Wise To Woo Peaceably by AshCatchem
Fandoms: Star Wars Prequel Trilogy, Star Wars Legends: Jedi Quest Series - Jude Watson
19 Jan 2025
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It Be Like That was considered the quintessential Kanim comedy, where Umi Skywalker, the slave, tricked her master Attica and her love interest’s master, Geordie, into falling in love, by talking loudly behind their back like this. It was the only Kanim play to ever be translated to basic, in fact. And Darra and Tru were taking a galactic literature course…
Anakin abandoned his plan to train, and instead went to find Ferus, hopefully alone
~
Much ado about space idiots, apparently
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I can be mature when I want to be by WhiteRequiem
Fandoms: Star Wars - All Media Types, Star Wars: The Clone Wars (2008) - All Media Types, Star Wars Prequel Trilogy
02 Jan 2025
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Summary
Quinlan and Anakin have a surprisingly mature conversation and the gang hangs out at the pool.
A frenzied battle commenced, shrieking, loud smacking and splashing.
Finally something interesting! These fools were going to sit in the garden and gossip quietly all afternoon. Well that's why I'm here, Quinlan thought, gotta make sure everyone is having fun!
Series
- Part 7 of Summer Paradise
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as the world caves in by JaggedEdges
Fandoms: Star Wars - All Media Types, Star Wars Prequel Trilogy
24 Nov 2024
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Summary
from: askywalker.jedi.cor
to: okenobi.jedi.cor
<if we were the last two people in the galaxy, would you repopulate it with me?>
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A change of perspective by Hilimi
Fandoms: Star Wars - All Media Types, Star Wars Prequel Trilogy
17 Nov 2024
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Summary
Spending a day in his Padawan's shoes – literally – was... instructive, to say the least.
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The wounds remain and the scars never fade by Hilimi
Fandoms: Star Wars - All Media Types, Star Wars Prequel Trilogy, Star Wars: The Clone Wars (2008) - All Media Types
27 Oct 2024
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Summary
All his life, Anakin had had to endure mockery when people saw him naked. That is, if they did not act openly disgusted. They would walk away, saying it was impossible, and he would stand there, hurt and humiliated while they laughed or carried on with their ‘jokes’.
A joke was only funny when everyone laughed.
Rex did not think his difference was laughable.
He was the first.
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I've Got Two Secrets, But I Only Told You One by Anonymous
Fandoms: Star Wars - All Media Types
07 Sep 2024
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Summary
Anakin was expecting things to feel different after a night of closeness with his valet Obi-Wan. Anakin was about to be disappointed.
Series
- Part 2 of Obikin Regency Vignettes
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The Plan by Sparky_Speirs
Fandoms: Star Wars - All Media Types, Star Wars Prequel Trilogy
30 May 2024
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Summary
As much as he hates to admit it, Anakin is Touch-Starved. As a young padawan, touch was uncomfortable. It reminded him of Shmi, and so he avoided it. As an older, touch-desperate padawan, he comes to regret his reaction heavily. In need for a hug, Anakin sets a plan in motion to get Obi-Wan to touch him, even if it was simply a mere brush of fingertips. Obi-Wan is oblivious to the young padawan's struggle.
OR
Anakin creates plans to try and get Obi-Wan to touch him, but it doesn't work, leaving him worse off than before. It takes a while before Obi-Wan notices Anakin is struggling, and he tries to resolve the issue before it is too late. He doesn't succeed the first time.
Series
- Part 1 of The Plan
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The explanation by Hilimi
Fandoms: Star Wars - All Media Types, Star Wars Prequel Trilogy
29 Mar 2024
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Summary
Dex finally hears the whole story... and to say the least, he is not impressed by Obi-Wan.
Series
- Part 4 of In defence of Besalisk
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Picture Perfect by Meleth03
Fandoms: Star Wars Prequel Trilogy, Star Wars - All Media Types
13 Feb 2024
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Summary
Obi-Wan gets called to the Council because his padawan has been caught in the lower levels of Coruscant, again, though this time the council makes a proposition that leaves both master and padawan to face their feelings.
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Anakin Skywalker's intense piloting by Hilimi
Fandoms: Star Wars - All Media Types, Star Wars Prequel Trilogy
08 Jan 2024
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Summary
Dex had enough faith in Anakin to get them to their destination without blowing them up on the way, that was a fact.
That didn't mean that the whole trip went without any hitches, that too was an unfortunately a fact.
Series
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Maybe it's Crazy, Maybe it's Magic by Space Mace (LoveNLols) for Eden Pierce (ChunChan11)
Fandoms: Star Wars - All Media Types, Star Wars: The Clone Wars (2008) - All Media Types, Star Wars Prequel Trilogy, Star Wars: Obi-Wan Kenobi (TV)
17 Dec 2023
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Summary
Three strangers end up in the same rideshare vehicle once Padme Amidala’s 'Single Mingle Jingle' event wraps up for the night. The driver, Anakin, can’t believe hostess Padme, as well as other event attendee Obi-Wan, are both single. The three commiserate on lonely holidays of the past and present, and by the end of the night Obi-Wan Kenobi has managed to obtain two fake romantic partners to his family’s holiday get-together. Now they just have to keep up the pretense, which is suspiciously easy to do…
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to love is to choose and be chosen in return by veloursdor
Fandoms: Star Wars - All Media Types, Star Wars Prequel Trilogy
07 Dec 2023
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Summary
“Have you ever heard of sugar babies?”
Anakin Skywalker, a part-time student and part-time intern at Stewjon Motors, enters into a contractual arrangement with Obi-Wan Kenobi, the CEO of Stewjon Motors, to become his sugar baby.
The catch? Love is off the table. For both of them.
But Anakin has been a rule breaker since the day he was born.