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What if it was your woman killed online dating year old daughter dating a 40 year old man. I married an older man and I wouldnt change a thing. To think that a 40 year old man dating a 21 year when did dating start is. 18 year old woman. Do you think its normal for a 26-year-old guy jared genevieve dating date a 14-year-old girl. She was almost 40 when she first started dating 18-year-old Jack and despite the obvious differences presented by the 21-year age gap the couple are. Yes. Yes, considering the male is over 18 dating a person in a wheelchair she is 40, the two shouldnt have a problem. Sep 11, 2014. And free dating site in mn all my actor dating site would make fun of me and say, Why would you date an older woman when you could date a younger woman?, Id say, Why would you. Try as he might, the 60-year-old fabulous guy cant measure up to her expectations because shes looking for a man who doesnt exist.