That "nasty reporter" obviously knew she had a once in a lifetime chance here and took it to the extreme, by purposely leading the conversation to, what she knew he didn't want to talk about.
Again, it resulted in exactly the kind of response/feelings the writers of the show intended for us to feel.
Stewart's acting was great in that scene. He conveyed so much in terms of emotion. And I think it was an important scene to have to show that not everyone looks back on him fondly in 2399. I just thought that some of her turns of phrase were not really things a reporter would say in an interview, even if she was trying to twist a knife to get a reaction.