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For instance, if she works in human resource department, you can start your conversation by asking her some questions related to human resource. If you are thinking of fun questions to ask your girlfriend, you should ask her in a natural way. Be inventive to ask such questions which genuinely portray her characteristics. It is a proven fact that women like to talk about them and tell others about their experiences. Ask about her, what she likes or dislikes, her childhood memories, her fears, her passion, her embarrassing experiences of life etc.