Obviously, the characters in "Ask Not What..." are do-overs on their experience of high school. The story, however, is beginning to go into what I consider interesting historical divergence.
Secretary of Defense Robert S. McNamara was a brilliant man, but in the wrong role. In our timeline, he subsequently regretted many of his decisions that led to suffering and death in the Second Indochina War (i.e., Vietnam War, or what the Vietnamese call the American War). What if his talents were redirected, putting a square peg in a square hole? What if his deputy, Ross Gilpatric, perhaps the only senior official to whom both the top generals and the White House listened during the Cuban Missile Crisis, became the round peg in the round Secretary of Defense hole?
Major historical trends, however, do not preclude the extremely pleasant insertion of other pegs in other sorts of holes. It is a turnon to be told that you're having excellent sex with someone that just had it with the President.