"It was this or get a job elsewhere, selling clothes or consumable goods." There hadn't been any other viable options that Diana considered. If Emma and the like turned out to not be capable persons, well. It would be a hypothetical shame, yes, but her time was better spent helping them to become better town protectors than earning 'coin' somewhere else.
"Do you have a problem with people knowing where you're going?" Diana guessed that either Babydoll had something to hide or slanted towards working very independently, and her first impression led her to presume the latter. She nodded approvingly at the katana, recognizing the fact that it was a well-made weapon and that she must have some capabilities and skills if she wielded and referred to it in such a casual manner.
"And how do you plan to get to the boat? Swimming?" It was an innocent question, but it could've been misconstrued as more accusing. "You'll need transport that protects you from whatever tried to pull you in, of course."