Click the Smarm can on Rupert, the "Could I borrow that puzzle of yours" chat option will have a different result, but it doesn't ungray to indicate that it's interesting again.
Unfortunately, I think this is a common issue in the game and pretty tricky to improve without rewriting and restructuring a lot of the dialogs.
We only noticed the option to change the color of used dialogue lines pretty late in the development process when almost everything was already set up.
"Man, we're gonna get so much pie when all these droids start coming back."