definitely! if she's the sort to sit at a counter alone or even someone sitting by herself that he's noticed a few times, he'd be prone to striking up a conversation without preamble, especially after a day where he's not actually spoken to a lot of people because he was eyebrow deep in legalese and paperwork. 'pass the salt, sugar' can easily turn into an hour-long getting to know you conversation with him while he shovels meatloaf and salad into his face. i'm game for however long you want them to have known each other, too. the last couple of years he's lived in palo alto, but he can pretty well call his office in san francisco his primary residence during the week.