If you are a native speaker, rarely.  Otherwise, all the freaking times (for the first ten years or so).<p>E.g., consider the difference between a &quot;cool guy&quot; and a &quot;cool attitude&quot;.  If you think about it, they describe almost totally opposite situations.<p>Or consider &quot;No, it&#x27;s cool.&quot;  After all, &quot;it&#x27;s hot&quot; means the temperature is high.