A woman of this age can fall into one of the following categories divorced widow a lady who did not enter into official. 300 single women over 40 reveal their biggest problems in dating i find very few men attractive in my eyes. there are lots of quality men looking for smart successful women their own age. The truth is that the number one thing a man is attracted to in a woman is confidence. I loved him but honestly, i got a lot of attention from men of all all ages and i have to admit, i liked older men because they come off as very mature but le. i am not saying it will never work, but take it from someone whos been there, it is very difficult. I have thought about this many, many times, but i cannot pinpoint where the attraction co. Of course a 70 year old man dating a 20 year old girl is repulsive but 40 year old man with a 23 year old is not a problem. too often women over 40 rush back into dating because they are accustomed to being in a relationship, says monte drenner, a licensed counselor and consultant. They feel like they need one or they are pushed into the dating scene prematurely by well-meaning friends or family. Once upon a time, when the relationship gods were smiling at me, i dated a 40 year old man. Hope despite the stereotypes, i am a 46 year old man who is dating a 53 year old woman. So i am not only not dating a 27 year old gal, i am dating a woman who is 7 years older than me! I think bobbi said (please correct if i am wrong) that most guys date women who are within 5 years of their age, and some of us like the wisdom and beauty of.