Two highlights that stood out:
• When during the campaign, a young reporter showed up at an Obama event. He had brought along a young woman he wanted to impress. Obama mistook the reporter for a student and then proceeded to make comments about how baby faced he was. The reporter wrote that Obama had ruined his chance with the woman. Obama called the reporter to apologize.
• When Obama was an actual guest, he was discussing how the drawers in the desks in the Senate had the carved names of all the Senators that had sat there. When they made jokes about vandalism and such, Obama joked that he thought about doing it with spray paint... you know, being the only black senator and all.