Milo first met Max while she had retired from piracy and was using the alias “Annie”. Despite the fact that he was intimidated by her, he charmed her and eventually they were married.
They lived a few quiet years as Milo and Annie Parker, running a jeweler’s shop in Arandale, until their lives were uprooted when Max was blackmailed which almost resulted in Milo’s death.
When Max suggested they head for the safest place she could think of, the Isle of Teeth, Milo quickly agreed.
Excited by the prospect of becoming a Pirate, Max trained him how to use firearms as she thought that was the safest option for him, and it aligned well with his strong interest in tinkering and arcane technologies.