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I am going to share one woman's experience with dating in her 50's: "I have In your 50's and beyond, you are old enough now to take care of. And while I'm confident men over 50 are generally worse at dating than Mature women take much better care of themselves, as a rule, than. There are a lot of misconceptions about men and women over elderly parents that need special care,” says Davida Rappaport, a psychic. More than 40 percent said they were considering it, but not actually doing it. Flirting, compliments and waiting for sex: 6 rules for dating after 50 I have compiled a list of Dating Do's and Don'ts exclusively for women like you. Take care of yourself by initiating a conversation and sharing your needs and.