According to the thread I've found, "echar una cana al aire" doesn't necessarily mean that you are unfaithful. From that point of view, letting your hair down or having a fling have the same meaning. To my mind, "echar una cana al aire" has the connotation of being unfaithful, in which case, it means "having an affair". Have a look at the three threads on the topic at the end of the page, in the forums. I'd personally go for the third one:
http://www.wordreference.com/es/en/translation.asp?spen=echar%20una%20cana%20al%20aire
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