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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.

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It is possible that the difficulties with relationships, both past and present, had a lot to do with being raised without the real presence of a father. Without knowing it is difficult to say how or why except that, perhaps, you never learned how to relate to and trust a man because your father was not a presence in your life.

Unfortunately, knowing that about your father does not help you very much in the present. My educated guess is that you push any possibility of a serious relationship away from you. That is not to say that you do not want intimacy in your life. To the contrary, I am convinced that you always wanted intimacy and that you still do. So, why would someone push away the possibility of a real relationship?

There are a couple of possible reasons for avoiding a deep relationship. For example, some people believe themselves to be so awful that they fear a significant other will discover the truth and come to hate them. Another possibility is that some people fear being dependent on another person. The fear is that they will lose their autonomy or become entrapped and rendered helpless. I do not know if these sound familiar to you? There are other possibilities. It is a fairly safe bet for me to guess that you choose men who are unavailable or undersirable as a way of distancing yourself from committment, just as you suggest above.

That is why I am suggesting that you enter psychotherapy with a clinical psychologist or experienced and well trained clinical social worker in order to learn what it is you are avoiding. In other words, it is not a matter of dressing better but of learning about your patterns of behavior and the reasons for those behaviors so you can bring real change.

I understand that you are dismayed about your age. However, I can assure you that people fall in love even later in life. Remember, you are not getting older, you are getting better. Remember the old song, “Life Begins at Eighty?” Well, you do not have to wait until you are eighty to live your life.

Good Luck

More "Ask Dr. Schwartz" View Columnists

  • Gina Pera

    I would offer another possibility before you seek therapy.

    It could be that, while your childhood relationship with your father might be a continuing influence, there are other issues. Brain-based issues.

    It sounds like neither of your parents were exactly stable or very high-functioning. Perhaps that is because one or both suffered from an undiagnosed mental health condition. Because these are often heritable, you might suffer from a similar condition or even a combination of their conditions.

    If you are reasonably attractive, intelligent, etc., it seems to me that you might have trouble reading social cues. And so you don't recognize "trouble" when you see it coming. Also, you might "freeze up" when encountering more suitable matches due to social anxiety.

    This can be due to many factors, of course, including childhood patterns. But they can also be due to neurocognitive disorders such as ADHD, Asperger's Syndrome, and even anxiety disorders. The good news is that, for many of these conditions, there are very helpful treatments -- sometimes medication and sometimes therapy but sometimes both.

    If I were you, I would find the best general psychiatrist in your area and pursue a full evaluation to consider all the possibilites. Before that, I would read a couple of good medically sound books that decribe, in layperson's terms the subtle (and not-so-subtle) signs of various mental health conditions.

    Two good choices would be

    50 Signs of Mental Illness: A Guide to Understanding Mental Health (Yale University Press Health & Wellness), by James Whitney Hicks, MD.

    Shadow Syndromes: The Mild Forms of Major Mental Disorders That Sabotage Us, by John Ratey, MD.

    Good luck!

    Gina Pera, author

    Is It You, Me, or Adult A.D.D.?

  • Caroline A Gould

    Oh, for crying out loud! Don't make her into a nut job! The situation she has described is not about her, it's about current demographics in North America and the woman is correct -- there are no obviously available men lurking about out here! I live in the midwest, am 58 and have not been involved with anyone or on a "date" in almost 30 years and I do not accept your blind search (of either of you) for a psychiatric diagnosis for either of us. Little did I know it at the time but perhaps 40 years ago I was speaking with a faculty mentor who was then my age and experiencing the same thing. She talked about sublimating those sexual and romantic feelings and moving on to conditions that are manageable. You folks OUGHT to know that statistically there are very few men available for all the women our age who are wanting relationships. My advice is that she surround herself with a wonderful group of friends, get a dog or two, and find other interests. Travel -- don't throw your money away on therapy.

  • too late

    Thank you, Gould, for telling it like it is. Sublimation. Cats and dogs are more loving and they don't notice your wrinkles and sags. Plants, animals, nature, enjoy what is and don't fret about some shallow man. Forget the men. They're all fantasizing about 20 year olds. Walk away. And, frankly, if you're broad minded (pun intended) you might consider an intimate relationship with a female. Hugs at the very least, would be nice.

  • Susie

    I agree with the lady who mentioned to surround yourself with good friends and create the life you want with or without a partner. Definitely though, do not take it personally, you're among friends and you're perfect and beautiful as you are. Remember too, you are in good company, half the planet more or less is single these days - must be an evolutionary thing.

    I too am single and what I've learned is to take charge and create my own grateful for what I have.... and pray and focus on the INtangible concepts I seek in life (love, security, connectedness) rather than the tangible things (boyfriend, children, etc.). God will definitely create and deliver the INtangible things - he does that for me all the time. God is very creative! : )

    You are a blessing to this world know that, accept that, and trust God..... and go with HIS flow for your life.....pray for the intangible desires of your heart. Remember its not always what we want, but what he wants and created us for. Peace!

  • Grace

    I am a 55 year-old woman. Your story sounds like you are talking about me. Recently, however, I have met a man who seems to really be a keeper (attractive, my age, single!), and I find myself mentally looking for reasons to push him away. I think it's because of one of the reasons the doctor mentioned: I think he willl find out I'm not good enough and leave. I am truly struggling with this.

  • Leslie

    I believe the whole merrygoround of having boyfriends and being comfortable with men is established at an early age by practice. As with anything, being good at something requires practice, that means going out with guys that you're not bothered with and developing your social skills along the way. I say this in hindsight - as I recognise myself in your letter. At this stage, I feel you have to be comfortable within yourself and find your own inner peace. In this world of desperation, self assured people are attractive. Get a cat, they're perfect company and you're never alone with these adorable little creatures who dont care what age you are.


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