Yes, I do fantasize about what it would have been like to grow up in the post-WWII era, in the 50's with the big band musicians and fashion. I would love to have been one of Rosemary Clooney's back-up singers, touring across America and on USO shows.
However I think often it's a matter of not being content with the life one has now, and hoping that a past life was better.
Sometimes I have memories so vivid, of a house or people that is so three-dimensional that I awaken with an aching longing feeling sense. Were these real places in my life, lost loves?
I think I spend more time wondering not "What was?" but "What if?" -- alternate paths of my current life. It's not hard -- I see the regret in an old love's eyes, as I say goodbye everytime we part from a social event. Knowing that a lie told by another profoundly affected our lives, and had it not happened it's quite possible we would be growing old together with a houseful of children.
Would I have gone to college though? Would I have stayed in college the first time round, instead of expressing my freedom from the discontent at home by drinking and cutting classes? I really don't know.