After a few tries, I finally got it!
The table cloth trick eluded me for a while, I must admit. I puzzled over it for a long time. The plate was large and heavy - lots of mass, lots of inertia - and the fork and knife had some weight as well. The plastic wine glass kept tumbling over, and I replaced it with a plastic cup with a larger base (more stability), but the place setting just wouldn't remain at rest!
Why, Physics God? Why?
A few minutes later, I realized suddenly that the "table cloth" I was using was both too long and too thick. My pull force was being transferred to the dinner objects in too large of an amount and for too long of a time (the time for the cloth to be fully pulled from underneath), and the objects had a farther distance to travel before coming to rest on the table - more time for them to tumble over or slide off.
I replaced the failing cloth with a smaller, thinner cloth. Then...
FINALLY, SUCCESS (However small and poorly done)
My father got the trick down in one try. Maybe it was because he already knew about physics...
Pictured: Cheater