Rebecca grew up as a shy, conservative young woman bathed in riches, and beauty, and was descended from a wealthy respected family. However, Rebecca's came from a long line of Osborn women who were seemingly very manipulative and cunning. One even arranged for John Wilkes Booth to assassinate Abraham Lincoln just for spiting her. Rebecca favored these ancestors, and was very eye-catching toward the men in her day. During her teens she fell for a local boy in her hometown, but was unable to be with him due to their different social strata's. At age 17, when she was a bridesmaid to her friend Ivy Winthrop's wedding, she slept with the groom's father, Alistair Crane. It was Alistair who introduced Rebecca to "satisfy the appetite of men".