Wright engaged in a love affair with Edwin's wife Mamah, with whom he went to Europe.
After Wright went off to Europe with Mamah Borthwick Cheney in 1909, Isabel Roberts was among the remaining Oak Park Studio employees working to complete Wright's unfinished commissions.
Woolley was prominently characterized as a devout assistant in Loving Frank, a fictional novel based on facts regarding the affair between Wright and Mamah Borthwick, told from her perspective.