Ok, I'll try to explain it this way...
"to be in the swim" is an informal expression meaning "knowing about and involved in what's happening in modern life"
if someone is "out of the swim" it's the opposite, they do not get it, have no clue what's going on around them. Just like me :))) I was away for 3.5 years, just came back and have little idea of what's going on in the place where I live; i was out of the swim.
Hope it helped...