Milo can win debates, but he's learned that he doesn't have to if he can just rile people up. it's a mistake to fall for the bait, but it's also a mistake to think that he's going to go down easy in debate.
Also, the key to writing a good female character is the same as it always has been: Just write real characters with real responses that have real lives. Give them a life outside the story and then put them in the story.
This is also the rule for writing any character.