Sammy Wing is the man that married Chessy twice. He is a photographer that lives in California now. Maybe has always looked up to Sammy as the only true father figure she has ever had. Ted finds Sammy and convinces him to allow Maybe to stay with him so that she won't be homeless anymore.
Sammy is obsessed with Chessy and has never gotten over her. Even though he has a new model girlfriend that is the younger version of Chessy, Willow, his house walls are still full of photographs of Chessy and Maybe. Sammy helps Maybe land a job as a nany, but supports Maybe when she turns down the job to work at the taco truck instead.
Sammy thinks of Maybe as his own daughter. He still thinks of Maybe as his stepdaughter, even though he and Chessy are no longer married.