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(+2)

I'm at the truck stop, how do I interact with the Diner for the job there? The only place I could access is the motel, which I can't afford to work in. (Might be spoilers but does it pay well enough to afford the dress once you can?)

Yes, the motel pays very well, much better than the bar (I'm not familiar with a diner)

do you need all the maid apparel or just the dress?

(+1)

The dress is enough, though you might like to not bare your nethers