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This has been on m mind for awhile.
In the episode City of Theifs, Jake "accidentally" steals some boots and can't walk through a force field with Finn because he had stollen something. But in the episode Apple theif Jake tells finn that he used to live a life of stealing and hanging around sketchy bars. Which I feel would be hard for Finn NOT to know because they grew up together. But if what Jake says is true then I think Jake "accidentally" took the boots so finn wouldn't know that jake used to be a theif before finally telling him while looking for free trunks' apples