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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. If you are seeking to meet men over 50, first ask yourself what kind of gentleman you want to meet you do not want to meet a world traveler if you like to stay at home, nor would you like to meet a sports fan if you have no interest in sports. Single parents success stories dating after 40 8 tips for dating men over 50 tip #8 – a lot of men over 50 are pretty insecure when it comes to asking you out.