I would say try Nietzsche, just 'cause I think his subject matter and stances in summary are appealing and easy for the lay person. He's also good 'cause he goes far deeper than you could have initially anticipated, and has been an influence on a good number of 20th century thinkers and is thus relevant.
He can even...no, he definitely should...powerfully shake your own self-understanding if you try to digest him in full, so that you will start weeping and crying about how horrible life is at the beginning of the evening, then by midnight, have reached a private epiphany wherein you want to dance naked on the street from the joy of realizing just how full life is.
tl;dr, Friedrich is the bard of feels