#obibail

[obiwancreampie]

bail and breha, who have been trying desperately to sleep with obi-wan for years: flirting madly and with hardly any subtly at all anymore

obi-wan: my friend bail :) who i am ever so slightly attracted to :) but who is very happily married to breha :) ah well, its for the best :)

[padawansuggest]

Anakin: Guess what, I got a SPS5 (SpacePS5).

Obi-Wan: You mean, Padme got you a SPS5 (Space PS5).

Anakin: No, I paid her back for it.

Obi-Wan: How? We never have credits- oh, are you running card scams like the clones do? Cody’s been trying to tell me how they pick their marks to grab cards off of, but honestly? I just go to Satine and Bail when I need to pay for something. I have them on speed dial.

Anakin: Oh, no, I didn’t use money.

Obi-Wan: How’d you pay her back?

Anakin: I let her handmaidens run a train on me and film it for their holiday orgy.

Obi-Wan: …there is so much going on in that statement, I’m gonna just nod and move along. That’s how I pay Satine and Bail back too.

Anakin: You don’t pay Quinlan back like that?

Obi-Wan: Does Quinlan look like he has credits either? No.

[onslaught-xavier-lehnsherr]

The size difference 🫦

[jebiknights]

I don't mind headcanons that Bail and Obi-Wan were friends before the clone wars started (and I don't think we're told either way in current canon - as far as I'm aware), but the legends meeting -> near death Speedrun to being TOO close is still my favorite iteration.

Bail being like hey I have a spy who has information on the Sith/a Sith planet but we have to meet her in person to get the goods. Obi-Wan, recovering from a speeder crash, being like this feels like a trap but we really can't ignore this Intel can we. Them getting stuck on a small ship together. They both think each other is kind of stuck up. Bail watching Obi-Wan meditate shirtless.

Meets the spy only to immediately get caught in a firefight and Bail has to experience the realities of war for the first time and it changes his view on the conflict forever. They get to the Sith planet and it is immediately Obi-Whump time in the best way, they are both having the worst times of their lives. They still aren't really getting along. Obi-Wan has to get Bail to promise to kill him at one point if it gets to a certain point. They manage to make it out through the skin of their teeth with five million in jokes and a friendship so close that it makes literally everyone else uncomfortable. What could be better than this.

[underdark-dreams]

It is, quite literally, only mentioned one time in game, but I’m SO fucking curious about Cal, Lia, and Rolan’s mother. What was she like?? How did Rolan become part of the family?? Does she look more like Cal or Lia? Is their father even in the picture? I want to know so much more about their backstory that it’s driving me insane LMAO

If you haven't seen them already: may I present @obibail's headcanons about this very subject, because they are so wonderful and bittersweet! They have been feeding me for months, and to be honest, everything they wrote here feels so perfectly canon. I just accept them as such at this point 🖤

[ahsoka-in-a-hood]

Hey keep referencing Obi Wan ‘serving’ Bail during the clone wars without showing Obi Wan serving Bail during the clone wars and I’m gonna just start headcanoning that they had a really involved service kink affair. Obi Wan playing full ‘knight serving his liegelord’ while sucking Bail’s dick. Really kinky but also really romantic. That’s obviously what Bail was talking about. The sex.

[captaingondolin]

50% of my brain: OBIBAIL HUG! OBIBAIL HUG! this makes me a happy shipper!

the other 50%: do you think this is the last hug Obi-Wan ever got? after this he’s looking at 10 more years in the desert and then death

[phoenixyfriend]

I want fics where Qui-Gon tries to be stupidly overprotective of Obi-Wan.

"Stupidly" in the sense that he figures Obi-Wan can take care of himself in a battlefield, but if that pirate touches his hand and makes an innuendo one more time--

(Admittedly this is inspired by me reading Jangobi fics and wanting Qui-Gon to try to block off his twenty-something apprentice from Getting Some from the Mandalorian dude because Qui-Gon disapproves of Obi-Wan's taste in partners, sometimes.)

(Obi-Wan pointed out that Qui-Gon had also gotten in the way with Quinlan, Siri, Satine, and Junior Senator Organa, and Qui-Gon hadn't disapproved of Obi-Wan's tastes then, he just wants to meddle.)

(Something something prude Qui-Gon who is convinced Obi-Wan is going to get his heart broken every time he finds someone, because Jedi.)