I need to have a difficult conversation with someone and as trite as is sounds would like to do it some where public that will also "softens the blow" so speak. So nothing overtly romantic, overtly sports related and ideally nothing too impersonal (Cheesecake Factory and the like). Doesn't have to be a sit down restaurant per se but it should have good lighting and good food options. Excellnet cocktails a plus.
Cost is a non-issue, and ideally should be in Boston proper, South End and waterfront OK, North End would work too. Not looking to do JP, Brookline, Cambridge, etc
I live in the burbs these days and my treks in Boston usually end up in chinatown or "special occasion" places so feeling a little out of the loop on the day to day dining scene.