I bought my first helmet in college, after a pretty scary near miss when I almost got left-hooked at a busy intersection in Madison (it was one of those Vetta units that looked like an imperial storm trooper prop). I have faithfully worn a helmet on virtually every ride since then (and because I am pretty cautious, have never needed it).
Today I charmed my wife into getting out her bike and going around a local lake. The entire ride was going to be on very quite side streets and Multiple Use Trails, and I could not find my little beany thing I wear under the helmet on cool days. So, I rode without a helmet.
It felt so... naughty, at first. Riding helmet less? How irresponsible! What kind of example does that set? I was surprised at how these thoughts were playing through my mind as I headed down the hill towards the MUP. I also secretly hoped for some kind of taboo instant gratification for this minor act of disobedience - the wind blowing through my hair, etc., etc.
Sadly, my lidless ride was nowhere near as liberating as I would have thought. Certainly not like skinny dipping. Not even like sneaking into better seats at the Metro Dome. In fact, after the first 10 minutes or so, I pretty much forgot all about it. It's kind of disappointing when your minor acts of rebellion turn out to be mundane.