Willow starts dating a boy and Overlord does not approve. Weaver is worried that Bebe has a crush on him and does everything he can to convince her not to fall in love with him.

Overlord finds his place with a group of Live Action Role Players and rises to become their leader. Meanwhile, Flower and Jim won't allow Willow to use the car until she passes their own bizarre tests.

After Jim errantly accepts a system update on R0-FL she becomes his assistant and stops at nothing to make sure he accomplishes the task of relaxing. Overlord, meanwhile, hires his nemesis Petey to be his assistant.

The Underwoods look forward to taking their yearly family portrait without Overlord, but their cousin goes to extreme efforts to get in the picture. Willow tries to impress the cool girls.

Overlord helps Weaver with morning announcements and uses the opportunity to hypnotize the adults at school. Jim drags an unwilling Willow to 'Bring Your Daughter to Work Day'. Flower has trouble letting an adorable hedgehog go.