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Annie and George eventually separated, apparently due to Annie’s drinking and "immoral ways".
By the late 1880s, Annie Chapman had become involved with a bricklayer named Edward Stanley. The two only seemed to meet at weekends, but Stanley frequently paid for Chapman’s bed at Crossingham’s Lodging House.
On, or about, 1st September, 1888, Annie got into a fight with another prostitute, Eliza Cooper, who was said to be a rival for Edward Sranley's affections. It resulted with Annie having a black eye!