As Angel draws pictures of Darla, Wesley expresses his concern that Angel has become obsessed with her. Meanwhile, Darla is haunted by memories of her past. In 1609, Virginia Colony, the human prostitute Darla lies in her deathbed, covered in sores from the syphilis that is killing her. She receives a visit from the Master, who takes her life and makes her a vampire. In 1760, Darla brings Angelus before the Master, bragging about her wonderful new creation, but Angelus' lack of respect towards the Master results in him receiving a beating. In the end, Darla chooses Angelus over the Master. In 1880, while strolling the streets of London, Angelus, Darla, and Drusilla bump into a man named William, later known as Spike. In need of companionship, Drusilla makes him into a vampire. In 1898, Darla begs a Gypsy to halt the curse on Angelus in exchange for her protection of his family, but unfortunately Spike has already slaughtered the Gypsy's family. The next year, during the Boxer Rebellion in China, Angel tracks down Darla, and - despite being cursed with a soul - asks her for a second chance to rule at her side. However, when he comes upon a terrified family he distracts his vampire companions from them, then tries to express excitement when Spike reveals he's killed his first Slayer. Angel returns to Darla, who demands he prove he's evil. She says she went back and killed the family in the alleyway, but kept their baby, which she wants him to kill. Angel's soul prevents him from hurting the baby and he grabs it and jumps through a window.
In the present, Darla calls Angel, telling him Lindsey kissed her and she needs to escape. Lindsey overhears, and he and a security guard try to restrain her; the security guard is shot. Upon violently persuading Lindsey to reveal Holland ordered Darla terminated, he rescues her and brings her back to the hotel. Lindsey finds that the security guard he supposedly killed is actually alive, and Holland reveals their intent all along was for Angel to make Darla a vampire again. However, when Darla begs Angel to make her a vampire, he refuses.