Advice on a Flashback scene

I’d like to frame a flashback scene to flesh out a bond between two characters in a Star Wars World game I’m running.

One character, Whomp Quince, is a twilek brain gearhead in a spider droid body that doesn’t remember his life as a twilek.

The other is a rodian scoundrel pilot, Bozz Debrill, who we established knew Whomp before he chose to become a monk and put his brain in the droid and why he made that choice… But we’ve left it to be fleshed out later.

I love framing flash backs that the players and myself turn into scenes relevant to the current story, but I’m a bit stumped on how to handle this one.

I had an idea to frame scene where the two are in a starship race but am unsure how to guide to some sort of revelation about Whomp’s past.

Do I just ask leading questions and create a montage with them based on the answers?

Do a create some sort of custom move for the race that result in choices that guide their narration?

Or something better that I haven’t thought of?

I like AW 2nd ed love letter style if it is not a focus of the game.

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I love leading questions that lead to a montage, especially once you establish that their bond comes in part from the fact that they both lost the race, and have a reason to mutually dislike whomever won (by cheating them, of course, this is Star Wars).

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Thanks. For the responses. Everyone!