Dating at Midlife/Help!


Hi Dr. Belove,

I appreciate the opportunity to ask you a question that has been perplexing me.

I have been in a relationship with a man (59 yo) for the last 7 months.  I have known him for about 20 years and over a period of about 6 years on occasion we would go out.  He always wanted to date at that point, however, he was newly divorced or I was in a relationship with someone so the timing was always a bit off.

Finally, fast forward 6 years and here we are.  Planets seemed to align correctly. He has now been divorced 6 years. During those 6 years he dated as well, in fact was in a relationship for about a year with one woman.  However, during that time he never spent the night with anyone or had sex with them.  When asked about not having sex with them his response was that he didn't feel that connection with them that made it right.

He is about 8 years older than I am and a genuinely nice and wonderful man.  He just confuses me at times.

First off, it amazes me that he didn't give up trying to get me to date him over the 6 years.  I would have thought he would have given up long ago.  He has a good sense of humor about it.  Often time something will happen and he will say something about it only taking him 6 years to finally make it happen.  And when asked why he waited all these years he says it is because he knew if he could just get me to this place, it would be good.  So it seems to be something he really wanted, and has wanted for a very long time.

We are intimate and do have amazing sex.  Once we took the relationship to that level, I asked him why if he never had sex with the other women he dated was he having it with me.  His response to that was because he felt that connection with me that he didn't feel with the other women.  

Here is where he confuses me though.  He is very loving, very demonstrative.  But he is not terribly articulate about how he feels.  Pretty much keeps me off kilter with that.  Now if I ask him he will tell me that he hasn't been this happy in a very long time.  That he is happy where we are now and that he can see us continuing to move forward with a future.  

But.... he still doesn't tell me he loves me, and we don't spend the night together.

I asked him one night if he could see himself loving me rather than just liking me.  He said "absolutely.  Obviously I more than just like you now or I wouldn't still be here."  and when asked about spending the night together #which he did 2 times when we first started dating but no more since# he said it was because he is just used to being home with his things and his routine.

I asked him if since he is so used to his home with his things and his routine, did it mean he was so set in his ways that he couldn't' see himself making a commitment to someone and having to integrate someone into his life on that level and he said "no, I don't think so".   However, he will still come to my house and lay in my bed and after sleeping for a couple of hours he will get up and go home anywhere between midnight and 3am.  He knows that I want that to be different.  He is well aware of my feelings about our spending the night together, but it doesn't seem to be changing.   On occasion I will be at his house and about midnight or so I will get up to go home and he has said a couple of times "you can just stay".... however, my feelings on it is that if he really wanted me to stay he would have asked me before I got there so I could have what I need in the way of toothbrush, pjs etc.  So I feel it is just hollow words.  When I get up to go he never trys to persuade me to stay.... so I don't really take it to heart.

So question one.... what is that all about?  I have been asking myself if it is a deal breaker... and I don't think so.  It is just perplexing and I am not sure how to change the dynamic.  And I can't help but wonder if that is a red flag for a commitment issue.

Now... the second question...  We spend literally every night together during the evening.   After work either I go to his house, or he goes to mine.  We either cook dinner together, or we go out to eat.  We snuggle on the sofa and watch tv, go to the movie, whatever.  Every night.  We have done this now for 7 months only missing a couple of nights.  When we are together the way he is with me, the way he touches me you can feel the love he has, BUT he can't seem to say that he loves me.  And, it isn't that he is just one of those guys that can't articulate it because I hear him tell his son and daughter that he loves them every time he hangs up from talking to them.  Everytime without fail.

Only time he has told me that he loves me was at Christmas #3 months after we started dating# when I sent him a text by accident #I was sending to my kids and best friend and didn't realize he was in the thread# saying I love you.   He responded back with I love you too.   I nearly died.  Because at that time we hadn't been dating long enough for me to feel that level yet and was shocked when he responded.   He came over to my house later and I apologized explaining what happened and told him that while I hoped that we reached that place in time, and that I really was enjoying getting to know him better that it was too soon for me and I didn't want that to put pressure on us.  He responded saying that he was very surprised by it and he didn't know what to say so he just said it back.  #basically saying he didn't mean it#   He has never said it since.  Even though I have quizzed him about could he ever love me rather than just like me.  Is he just afraid to say it out of fear that he doesn't know how I feel?

I have heard him tell people a couple of times that he asks himself all the time what I see in him.  Maybe he isn't secure in it?  I don't see how though because I am very open about what I want.

So open that I have asked him also if he could see a future with me because I don't want to find myself at this age dating someone for years and it going no where.  That someday I would like to be married again when the time is right and I don't feel like watching my life pass me by waiting on something that isn't going to happen.  #I spent my entire 40's with someone and it just didn't work out#  He tells me that he understands and yes he can see a future.  

Maybe he knows that is what I want so he can hold back, lay low and just take his time thinking he has me hooked so I am not going anywhere?  I don't know.

However, sometimes I find it difficult to "play house" in some ways with the cooking, cleaning, hanging out together every night and weekends.... but then not hear he loves me and one or the other of us getting up and going home at the end of the night.

How the heck do I read these confusing signals?  And... basically the age old question comes to mind of "how do you take it to the next level"?

Well, that's a complex situation.
There are probably are ten thousand things you can do.
For starters, bring a toothbrush and a few things and leave them there so you can spend the night without it being a special thing.
Just do it. As him for a drawer and some closet space. Make it simple and normal
Also, just start telling him you love him when you feel like saying it.
Again, make that normal.

He has his rhythms and you have yours.  I used to say that you can make a relationship change but you can't change the pace of change.
This might be one of those instances.
He is a man who decides slowly.
I have an astrologer friend and she tells me that scorpios make decisions like this, very slowly, like the change in a swamp. I know some folks like that and I don't know about the astrology thing, but I do know that folks have different rhythms.

Your fear is that he is holding back or being manipulative.  That is a possibility. the other is that he
simply moves slowly. But also that he's quite steady.

Also it sounds like he's one of those folks that is anchored by his own stuff.  Ask him to bring one of his pillows over to your house next time he plans on sleeping with you.  Have him leave a few things are your place just as you leave toothbrush and stuff at his.  Make these changes quietly without a lot of conversation.  He's slow to talk and maybe he's one of those folks that has to try the hats on before he buys them.  So make the changes in the non verbal realm.

Let me know how these suggestions land in your heart and what you decide to do.

Philip Alan Belove Ed.D.

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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