The term "Roofless" is used to define two (2) types of people:
1. Acknowledge someone who has the ability to make very harsh & demeaning personal insults against another person and not have any remorse, instead basking in the glory. (see example 1)
2. Praise a person before or after a dare, to whom the person is willing to take a huge risk that is highly embarrasing to themselves or another person. (see example 2)
When applied in a real-life situation, it is spoken or shouted AFTER the person has made the comment or accepted/completed the demoralising challenge (as given in the example).
Pronounced "roof" ~ "less"
Example 1:
Jack: Hey have you guys seen the new Terminator movie?
Daniel: No, but have you seen the one starring you in it?