Keep in mind that Bruce doesn't actually CARE about any of these dates - he only goes out on them to provide credence to his image of 'Bruce Wayne, Millionaire Playboy'. You can't very well be a millionaire playboy if you don't PLAY, right? So it's perfectly in keeping with his character that Alfred sets up the dates - his job is just to go out and act suave. I'm pretty sure Alfred has done the same thing more than once in the regular DCU.