mars

He starts this when Anakin is a Padawan and Obi-Wan has to go on a mission without him. He records himself telling Ani how proud he is of him and that he thinks that he'll be a wonderful Jedi.

Then every few years he makes a new video; he never throws the older ones out, instead he collects them and hides them in a box under his bed.

At the beginning of the war he makes a new video; it's right after Anakin's knighting ceremony - Obi-Wan is sent off world the next day, so he won't have a chance to film it later - so he's more emotional than usual. This is the first video where he tells Anakin he loves him. And then, because he doesn't think Anakin will ever see this or care, he confesses he's in love with Anakin.

And then he also cries a bit about not receiving Anakin's Padawan braid, something he'd been looking forward to. He tells Anakin he had this silly fantasy where they would exchange braids (Obi-Wan kept his own all these years) because it would only be fitting, since Anakin has taught him just as much as Obi-Wan taught him.

Then, during the war, he makes another video. He tells Anakin how very proud he is of him, that Anakin is his pride and joy, that he's a wonderful Jedi and Master to Ahsoka; that he loves him more than anything, and only wishes for Anakin to be happy, even if it isn't with him.

At the end of that last video, he adds a rushed addition - shortly before the Rako Hardeen mission, he records himself again to tell Anakin what's going on. He says he's sorry he couldn't tell him sooner, but his initial reaction had to be genuine; he tells Anakin he loves him and that he'll be home soon.

While Obi-Wan is pretending to be Rako Hardeen, Anakin finds the recordings. He watches the most recent one first but he doesn't watch it to the end. It's too difficult to see his Master talking about how much he loves Anakin, and he can't take that right now. So he never sees the part where Obi-Wan tells him about the mission, and thinks his Master is truly gone.

Over the duration of the mission, Anakin obsessively watches the recordings, all the way to the first one. He doesn't know what to do with the love confession - of course he's always loved his Master, but Obi-Wan always felt unreachable. And even now, when Obi-Wan fucking confesses to him, he is still out of Anakin's reach, and there is no way to ever get him back.

So Anakin tries not to think about that part. Instead, he gets fixated on the Padawan braids. He pauses the video and turns Obi-Wan's apartment (where he practically moved in; he only wears Obi-Wan's clothes) upside down in order to find his braid, and when he finally has it he ties it around his wrist. Then he goes out to ask Padmé for his own braid back (which he ofc does in a very calm and reasonable manner where he explains the situation to her. He totally doesn't just storm in and demand it back. Nope. Anakin would never). Anyway, as soon as he's back home (Obi-Wan's apartment) he ties their braids together.

maybe 3po is at the temple with them (for some reason) and in front of other jedi refers to anakin as “master skywalker-kenobi” bc anakin reprogrammed 3po to refer to him & obi as that.

So glad you asked @whispersofroses and I wil expand.