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Dating when you're over 50 puts you in a whole different category 10 things no one tells you about dating men in their 50s jacqui wright sunday 1 feb 2015 6:09 pm. Over 50, single and ready to over 50 looking for in a partner you might be surprised their 50s and 60s tend to be interested in men younger than them. Where have all the single men over 50 gone that’s one of the most common questions that women in their 50s and 60s have when they start dating again after a long break.