Depends on what we are playing.
I am horrible at video games.
In mathematics, you don't understand things. You just get used to them.
I have the result, but I do not yet know how to get it.
All physicists, and a good many quite respectable mathematicians are contemptuous about proof.
It depends on the quality of the program. Some 'against the computer' games allow you to set the skill level. Some games are definitely 'winnable' if you know the trick. eg. NIM if you go first.
You cannot teach a man anything; you can only help him find it within himself..........Galileo Galilei