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Come on now (I'm 66) and I would simply ask the person out. Call her up and ask her for dinner and perhaps dancing or, dinner and a movie. Don't live on 'what ifs' or 'I should have's.' I know it's difficult getting back to dating after such a long time, but I have divorced friends going through what you are and most of the time THE LADY SAYS YES! Please keep us informed and let us know how things turn out.

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16y ago
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Q: How Does a 50 year old man ask a 50 year old woman for a date?
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