To be honest, I am not sure where I learned this, but the theory is solid. Paul was the only one who mentioned the word "watchings" saying that he had a lot of them. When Jesus told his disciples to watch with him in the garden, he was using an entirely different word with an slightly different meaning. However, both seem to be pretty much the same thing.
As I learned it, "watchings" are times when one spends hours into the night praying. This may be planned, but may also be unplanned and spontaneous. Here's how it works...you are praying at night, or you feel compelled to pray; and while you're praying the prayers don't want to quit. You just want to keep on praying, but its getting late, and you have to work the next day. No matter how much you tell yourself its time to go to bed, something inside is compelling you to continue praying.
This might go on for 20 minutes, it may go on an hour, it may go on for several hours, or rarely you may pray all night.
Jesus prayed all night before he called the Apostles and he prayed into the night on the night he was betrayed.
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