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Answer: when she has a personality and can hold a conversation! If you could only hear one song for the rest of your life, what would it be? What is the coolest flag in use? It helps if he is really into movies, but feel free to skip this one if you are uncertain about it.
If he is insecure about his abilities sexually, jealousy, his work, or he just feels weird about his hairline, knowing this can help him gain confidence.