I would like to know what kind of girls Obama dated. What kind of a woman,besides Michelle really appealed to him? How did he come to the decision to marry Michelle? Sometimes he acts like he has negative feelings towards women,especially being so militantly pro-abortion. Maybe he really is bi-sexual? who knows,in todays world anything is possible.
Michelle was the "right" woman for the constituency Obama needed to win over. Given Obama's political aspirations and the neighborhood he picked to begin his career, his wife would have to be African-American and more a part of the Black community than he was. So Barack may resent having his options limited by his political aspirations.
Obama comes from a very different background from John Kennedy, but for both men the women they married may not have been the ones they'd have chosen for themselves if politics hadn't been a factor, and there may be some resentment about that.
It's clear that Obama had a problem with his father, and maybe with his mother as well but it's not always easy to separate out his own psyche from the problems that middle-aged guys do have with changing standards of political correctness.