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An older woman, whether more experienced sexually or not, appreciates a confident; yet humble not arrogant man. She is choosing to date you, so know that you have something to offer. Ask her questions, discover what turns her on; listen and ask for details or clarification.Her values are not the same as a younger woman Cheyenne Bostock — Ask Cheyb. Often younger guys try to outmatch the older guy, by pretending to be more experienced, worldly, wisely and even successful than he is.This is not what an older woman wants from a younger guy.Men are afraid to make mistakes, look bad or insult an older woman as if all older women were bitter, judgmental and fickle. Carmelia Ray Carmelia Ray is a certified dating coach, matchmaker and online dating expert.As a leading authority in the dating industry she has personally interviewed over 60, singles.