WinniethePooh,
That is a good question. Maybe there is someone big out there who has declared a horaas shoh that everyone is relying on. But I suspect that the Roshei Yeshiva do not know what goes on typical dates (outside of the very Yeshivish) after the first one or two. I have hard time believing that any Rosh Yeshiva would tell his talmid that it is mutar to take a girl to Dave & Busters or Chelsea Piers. When I was in the parsha it never even occurred to me to ask.