Good post Aries –
While your ideas are good, the major obstacle I see with boys and girls on a beshow is that they lack basic social skills needed to communicate with genders other than their own. Girls have somewhat of an upperhand becuase they ususaly have a year or so of experience working among men. But the boy? Poor guy doesnt know what hit him. My friend’s son was “coached” on the 15 minute drive from his house to his beshow on what to say and what to ask.
Best is to let the girl do the talking and for the boy to just nod a lot. Keep the conversation light. They can (and do) make up for it during sheva brachos. I see it in BP all the time