Sharon Baum met Bloomberg at a Harvard Business School alumni function (Baum had graduated from Harvard a year before, one of seven women in her class) shortly after he moved to New York. They dated casually. Even in his youth, Bloomberg had a tendency toward grand gestures. On the day Baum married another man in 1969, Bloomberg sent her a dozen long-stem roses with a card: 'I wish you all the happiness in the world.'

She complimented him on the pictures she'd seen of him walking with commuters across the Brooklyn Bridge. 'You looked really great coming across the bridge,' she said. 'But where was your hat?' Bloomberg grimaced. 'Ugh, you and my mother.' Then she changed the subject. 'Why aren't you running for president?' she pestered. The mayor's response was the same: 'Ugh, you and my mother.'