It's wrong to ask things that make people uncomfortable
Larry has taken an interest in a new friend of his and thinks the feeling might be mutual.
Larry wants to make a move on the girl.
Larry spends time getting to know her better before he flirts with her.
Larry starts to ask his friend questions that are very personal in nature.
Larry's friend feels comfortable enough with him to flirt back with him.
Larry's friend is put off by the way he is talking so soon.