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Five things i’ve learnt about dating in your 50s, by a man newly single after 28 years of marriage sink into a depression, or up your game and get out there when our guest writer, now in his 50s, became a widower, he wasn’t sure how to date again he has some great advice – from personal experience – for 50-something men going on dates 29. For those women over 50 who are reentering the dating scene, it’s hard to know what to expect in many ways, dating men is still the same as when you were in your twenties – communication remains key, intimacy is still awkward – but, with age and experience, comes some key differences he. Where do i meet single men if i’m in my 40s i am 44 years old and entering the dating scene again for the first time in 25 years where do you go to meet someone at my age i am not doing the online singles sitesthat is just scary to me i don’t go to church i am new in town, with a few happily married friends i have four grown who. Dating blog for men and women over 50 dating blog for men and women over 50 ® dating tips questions & answers the men's page the women's page top questions aug 26, 2015 5 things that stop you from dating meeting someone new is an adventure, especially if you keep trying to meet someone, and something keeps stopping you from meeting someone new when you are single and over.