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He has to make her feel that he likes her and wants to know her better. He can only do this by finding out what are her likes, dislikes, her future plans, ambitions and how she feels about him. Before asking a girlfriend any girlfriend questions he should be able to judge her mood. If she is in a bad mood or feeling low, it would be best to let her talk about what went wrong and why is she in a bad mood and feeling low. Coaxing her and taking a genuine interest in her feeling will make her talk about what went wrong.