Lyric discussion by stevenmw 

Cover art for Fool Around lyrics by American Analog Set, The

Definitely a married woman

There's a ring around She don't keep around She don't fool around When she fools around

I think "he gets schooled around" means she plays him. maybe he doesn't know what's going on? The "boy who never thought to fool around" means her husband was loyal.

So he moves around And gets schooled around Cause she fools around On a boy who never thought to fool around

I think the husband leaves the wife but then cheats on the next woman he was with

There's a girl in town And she's cooler now So he's moving out Out where it's cooler now

And he moves around And gets schooled around And he fools around On a girl who never thought to fool around

I agree. It could even be about a cycle.