Keeping Up A Conversation

After dinner, Roman went home and managed to finish his first Words with Pals game with Penny. He beat her by a measly three points and she immediately pushed the 'rematch' button because he got another request from her right after. 

He smiled to himself. This had been a good idea. If they kept playing like this, eventually he would find the right thing to say to get her to like him, right? 

But he still hadn't found the right words days later. He didn't want to start a conversation with small talk because it wasn't likely to go anywhere that way. He needed to make more of an impression; hopefully a less weird one than he probably had by randomly bringing up cheese. 

Roman wondered if he should do what Harry did and message her about the next weird/unlikely word he saw her use. Every time it had happened so far, he chickened out.