Thinking With Your Head or Heart

I was talking to a friend today who needed some advice on a matter of the heart. Why she chose to talk to me, whose record on the subject is short and unimpressive, is anybody's guess. But, it got me thinking about how much or little we learn from our past mistakes in these matters. I am not a big fan of the head-heart dichotomy but is it possible to learn to use your head more in so-called matters of the heart? I think so, for no other reason than we know ourselves better and we also learn the rules of the game. I don't mind to sound cynical but it is a game to some extent, and there are rules, especially around the distance and space that one accords to one's interest, especially in the early days. Those of us for whom this correct combo of interest and detachment doesn't come naturally have to learn it the hard way.
When I say learn about ourselves, I mean which attractions to pursue wholeheartedly, which to pursue to a limited extent and which to not pursue at all. Not all attractions have to be pursued, especially those that we know could be damaging for us.