A: What kind of jokes he has heard lately. What is his favorite dream would of been. When he was a little boy what did he always dream he would do in life.
A: That they really looked nice tonight. And that you had a really good time with her and would like to see her again if she would be interested in going out again.
A: If he asked you out then by all means go out with him. Don't you think your friend would go out with him if she was asked out? He would be interested in you since he asked you out first. Good luck