Nope, he wasn't expecting this. But unexpected hugs are often the best kind. He returns the hug, as you do and lets her back to her feet after a second or too.
"Hey, that means you have to keep out of trouble too, and like I said to Oliver, I'll hold you to that." Actually Oliver should just come with them.
"I didn't really have any expectations. Isn't there a Hibachi place near here?" He doesn't have any money except the stipend he brought along from the waverider. He does have an account still with sizable funds accumulating interest, but the funds won't be released for a few years according to his will and the paperwork required actually coming back.