Middle-Aged Female Never In Love

I am a 53 year old woman and, I guess, somewhat attractive (so some say). I still have a slim figure but am starting to look my age in my face. The problem is I’ve never, ever had a healthy love relationship with a man. I had some bad relationships in my teen years, no real boyfriend, though. I had a few brief sexual encounters in my very early twenties with two different men but they were never boyfriends or steady friends. They never took me out anywhere (in public) so I never could really call them “dates.”

Since then, I had only been asked out twice but I wasn’t interested in dating either man. At the age of 37 I was quite lonely and a man was attracted and attractive to me. It turned into a crummy short-term (two week) sexual affair because I was weak. Then I learned he was married and it made matters worse.

Another time, at age 41, I went out with a man who I wasn’t really attracted to and went to a cafe and to a movie. I thought I’d give it a chance, thinking that I might find something about him to like. However, he was just like all the rest in assuming that I would just go with him to his place for “a night-cap”,…yeah, right. I never even flirted with him or gave him any indication of wanting anything from him. I just wasn’t into him at all, so I asked that he take me home.

After that I have never been asked out by ANY man. I’ve had some real bad actors flirt with me or try to come on to me, but was not impressed, so avoided them. I was very attracted to three men in my adult years and none of them were ever attracted to me at all… so I seem to want what I can’t have. For some reason, I sometimes attract guys who are mentally challenged or have serious mental disorders of some sort, are married or are much older men, and they don’t seem to have a problem approaching me.

I don’t dress provocatively. I dress appropriately, with taste, and don’t wear much makeup. So, I don’t know why I attract bad apples in the first place.

Now I have been more open to the idea of dating but I’m not getting any younger. I realize that if hardly anyone found me attractive during my prime years,  it is unlikely that they will now. It seems nearly impossible to find a decent, available man now.

I live in a city with over 3 million people and while I have been very social the last 2 or 3 years, no single men that I am attracted to have asked me out. One seems to like me, yet even he’s backed off. The men here just do not ask.

Being rather old-fashioned myself, I will not ask a man out or make the first move. I also have been celibate for many years except for that 2 week affair. I do not want to go into any sexual relationship without genuine love and affection. I have never had those from a man whom I truely crave.

Seriously, I have not been kissed or held, even if it was only physical, in over 16 years. That said, I realize that I may be socially phobic in that I often clam up around men I find I am attracted to and feel like a teenager in that I get shy, anxious or nervous. But, I really think that it’s because I just don’t have any substantial experience in dating any man of good quality. I am currently going to activities in singles groups, so it’s not as if I’m hybernating.

What can I do to become more sure of myself and more attractive to the right kind of man? Is it something in my past that prevents me from a good relationship? Would it have anything to do with losing my father who I never really knew at that age of 7? He did not live with me and my mother and he was not married to her. My mother also had a few failed relationships after my father died. She later married and he adopted me and my sister but I was not close to him at all. He later cheated on my mother and they eventually divorced.

In what way would these circumstances affect me at this late date? I know there are some good men out there but they always seem to belong to someone else or they are not interested in me.