As a leader of the young social set, Jennie occasionally displayed a devil-may-care attitude. After a round of golf at the Burlingame Country Club in 1911, she and a girlfriend sped away in an automobile, drive 35 mph through the hills of Belmont and Redwood City. They were oblivious to Police Officer Mike Brown behind them.
Concerned over the safety of children walking home from a nearby school, Brown arrested Jennie and her friend and they were fined $25. Since neither carried money, the heiress promised a check would be posted at once.
Jennie’s relationship with Malcolm Whitman had grown serious Socially prominent Peninsulans were caught off-guard when their engagement was announced. Everyone wanted an invitation to what was billed as a magical scene out of the Arabian Nights.