Dating at Midlife/Love at 56


I've attracted a player and am in 'relationship' with him.  He calls me his girl.  What I want is the hot sensual relationship from a man who will extend himself into the rest of my life and be there for me.  I have been married, he has passed away.  I gave birth to three children, and just a month ago found out that I'll be grandma for the first time.  This man who is now in touch with me is 44, which makes me 12 years older.  I am not a model type, but he seems to be attracted to me and i to him.  It is difficult to dismiss a possibility that maybe he can be serious about engaging with me on all levels.  Am I capable of sustaining that relationship.  I can only be myself, but I know that maybe I can learn few things too how to be better when it comes to getting from man what he has to give and giving man what he should get from me, without feeling used or using.  I really want to maximize my chances.  How much can you help me?  And will you stay to see this relationship through some resolution?  Milica


Like a lot of midlife singles, you've found a lot of freedom and satisfaction in being single  and now you are asking some fairly deep questions about relationships. So go slow. Your questions are very intelligent.

You must be sending out some very inviting vibes to have fascinated a man ten years younger than you and also a "Player."

I am, of course, curious why you would call him a player. Usually a player is a man committed to not committing, to just playing around.

You said,  "Am I capable of sustaining that relationship?"  I thought you were going to ask if he was capable.

But maybe you have confused things.  A player is a player and it doesn't matter what the woman does.

That's also why the terminology is so useless. Many men and women play around, experience, adventure, do short term relationships until they get tired of it and until they figure out what they need to figure out. As one woman put it "I think I've sex with as many different men as I ever want to. I understand what that's about. Time for something a bit more substantial. "  Men say this too.

There are things you need to figure out.

Then folks usually settle down, a bit.  I know some who were players who settle into open relationships. They're not monogamous but they aren't predatory either. They just allow themselves and their partners to have sex with someone else now and then.  They're very deliberate about it. That's a whole conversation.)

But I think you want to know if you can catch him and keep him. Is that your question?  I'm not sure because "catching him and keeping him" is a bit of a manipulation and you want be authentic.  

Still you asking all the right questions:  how can I be more accepting and discerning and appreciative of who this man is and who he shows up int he relationship.  How do I show up  for that and not become manipulative or victimized.  Those are the Great Questions for datingat midlife.
The simple fact that you ask them speaks very well for you.  Keep asking them regularly. There is no one answer and being sensitive to these issues is a discipline, it is how you explore a relationship.

You'll probable want to start a journal. You'll want to develop your emotional intelligence and your ability to read him and how he's approaching you. You'll need to start noticing in more and more subtle ways what works and what doesn't.

Eventually, things settle down, but not ever completely.

Your question is the large question that people ask and which leads them to extended conversations with folks like me.

there is no One Secret. There are ten thousand small realizations. It's a very satisfying process.

Give some thought to having a few conversations with me, some coaching. Let me know

Meanwhile, I hope I did justice to your inquiry.

Dr Philip Alan Belove

Dating at Midlife

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Philip Belove, Ed.D.


Hi. I`m Philip Belove (that is my name, really). I`m 71 and I`ve been a psychologist all my midlife, the past 35 years. My specialty has been counseling and coaching other midlife adults.  I think we all figure things out as we go along, but even more so at midlife. Being between 40-ish and 60-ish and single is like being a stranger in a strange land. I`ve learned which questions help people find their own way. I created this category, I publish a blog at and I write articles for various web sites. My commitment is to help people 1) understand and improve how they deal with others, 2) understand the forces that rule the relationships they are in, and 3) make the decisions which will shape, or create, or end those relationships  so they achieve the goal of midlife development  to finally live with personal satisfaction. I`ve been divorced twice myself. I`m in a satisfying relationship with a fine person. I`m very interested in learning about your challenges and in offering what I can.


Professionally: Licensed Psychologist. Marriage and Family Therapist. Coach.Author. University Lecturer. Personally: I'm 71. I've probably made all the big mistakes, er, learned the big lessons.I've forgiven myself and made many apologies and I've made it into a good, stable, sweet relationship. I now have a perspective on midlife.

Please check out my book, Rabbis in Love, at Also my blog at The Rabbi book was done as part of a research project. My collaborator, Marilyn Bronstein, and I wanted to interview couples with very successful marriage and also we wanted to talk to people who cared as much about their spirituality as love. Maybe being able to love and be spiritual were one and same, we thought. So we found a rabbi couple and the interview was so astounding that we interviewed nine more rabbi couples. One dropped. They'd revealed too much. It's a fascinating book and, Jewish or not, religious or not, these couples do a lot of things right and there is a lot to learn from them.

Masters in Counseling Psychology, Alfred Adler Institute Doctorate in Consulting Psychology, focus on family therapy, University of Massachusetts at Amherst

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