*Younger Roman's POV*
Roman hadn't expected Penny's completely random line of questioning but he hadn't been too surprised. Harry had said she laughed a lot and would probably want proof of his sense of humor. This was most likely the best way she could think of to ascertain that for herself.
Despite the fact that this date was basically a question-and-answer session, the conversation flowed smoothly. Naturally. As if they had been doing this for years.
It was totally weird and creepy that a random person had been watching the two of them talk but he couldn't deny that the stranger's advice worked. Harry had also warned him that she probably thought he was too serious. Smiling less stiffly couldn't hurt.