Dating at Midlife/Confusion


QUESTION: Hi Dr. Belove,

I am in a state of confusion with regards to direction to take in my life right now as I get to a fork in the road.

I have been dating a guy for almost a year now.  He is 60 and has been married twice now.  During the time we have been dating there has been discussion about the "future" in terms of his saying that he can see us having a future, likes where the relationship is headed and is happy where it is right now.  Often reassures me that he thinks we are in a good place, are good together and can see a future, while at the same time continually telling me he is happy the way things are now and wants to take things day by day and letting things unfold as they will.  All fine and admirable.

We spend every day together after work, and every weekend together, however, he never will spend the night with me.  He will have sex with me, and tells me he loves me, but even though he knows I want him to, he won't spend the night.

He likes playing house with me all day, seven days a week, doing everything and going everywhere like we were a married couple, however, again he sends me home at bedtime (or goes home if he is at my house) and seems to be in no hurry to take any next steps toward commitment any time soon.

Until we started dating, I intentionally kept myself from getting attached to men in my local area because my children live out of state and I have always said when they got married and had children I wanted to live where ever they are.  I finally gave in and agreed to go out with him after several years of his trying to get me to do so, and it has been amazing.  Now I find myself a bit confused at what direction to take with things.

So, here is the dilemma.  I am at a fork in the road with my career.  My job is very stressful and quite honestly running me ragged.  So, I have decided to start looking for another job.  I am at a place where it is time for a change.

In order to make a change, I have more options if I look for jobs outside of my area.  Until he came along it was a no brainer.  I knew there would come a time when I would be ready for this change and there was nothing to stop me from doing it.   Now with him in the picture the decision is more difficult.

I struggle between two realities.  On the one hand, no matter how amazing my time with him is, and no matter that we do love each other... he has made no "formal" commitment to me for a future.  Just tells me he can see us together in the future, and believes the future looks good for us, however, he hasn't made any moves to really making a commitment to the future (engagement), and heck he won't even spend the night with me.

On the other hand, we are exclusive, we do talk about having a future when the time is right.

Lastly, one night recently he shared some really intimate details about himself that he was afraid would change how I felt about him.  That being that he does see us having a future, however, right now he doesn't feel he could be a good provider for me and that weighs heavy on his mind. (he is a real estate broker and the market hasn't been as good as it once was).  So this I believe has some bearing on his holding back and making things move so slowly.   He was really slow at becoming exclusive, even slower at saying he loved me and still won't spend the night with me.  It is almost as if he drags his feet on all things because he is afraid if he moves too quickly it will seemingly speed up the relationship to a place of committing to more than he feels he can take on since he thinks he isn't a good provider.

So... here I am trying to figure out what to do with my life's next steps.  I can stay at my current job even though I am not happy doing so... that way I can stick around to see if the relationship ever goes anywhere further.  I can miss taking an opportunity to be happy in a different job on a "I can see a future for us", but not a formal commitment.  Running the risk of that commitment never happening....

Or... I can look for jobs, take what makes me happy on that front and run the risk of losing what I have with him if a new job causes me to move out of town.

I have attempted to discuss this with him, however, all I get out of him is that he thinks I should look hard for new jobs in my area, and that if that isn't possible and my only choice is to take one out of the area, we will figure it out.

One day I was vulnerable to it and said something to him about it just didn't feel like it mattered to him if I had to move or not.  He said that was so far from the truth.  That it meant everything to him, however, he just chooses not to get worked up over something that may or may not happen.  We would address it when that time came.

Well... to me it seems a little late to wait until I get a job offer out of town to start discussing it.  

I feel so confused in that I am in my early 50's... and I don't want to pass up an opportunity for a job I would enjoy to spend the next few years of my life "dating" someone that never takes the final step to lifelong commitment for whatever reason.

Yet it is equally hard to take a job elsewhere and walk away from a chance at being with an amazing man that I do love SHOULD he decide to make that commitment.   

So, how do I untangle this mess and decide what is right?

Where is Solomon when you need him?
This is a really tough call.

No matter what you do, it's a risk.

Maybe there is a hierarch of risks.  The most fundamental, maybe is, whether or hot this relationship has a future worth sacrificing for.
I think that's the right way to word it.  
I suspect it does have a future and could continue as it has for a long time

( I hope I can do justice to these subtle calls in writing.  )

A few things about him jump out at you, seem important to you,
and I trust that intuition.
One, of course, is that he can't have you stay the night and that's after a year.
So that means something important and we don't know what, but something.
It seems to have to do with a kind of timidity on his part, a lack of faith in himself,
a fear of being, if not dependent, then not someone you can lean on. Or maybe, he thinks that
if a man isn't a "provider," then he's not really a mature man.
but whatever it is, when he's discouraged about himself, he holds back from his connection with you
and that does seem significant if you're looking at a long term relationship.

It's also possible that his timidity is more generalized, maybe even idealized (it does have a good side, called
modesty and humility) and all that might have bearing on his discouragement about being a provider and a
leader. So it gets really complex at this point.

He's got a strategy, which is, one day at a time, don't get too worked up, and so on.
He recommends that to you

I suspect you have a different preferred way of meeting challenges
His ideas clash with yours.

I think that in this you might be able to see foreshadowing of how he likes to deal with challenges.

So one of your decisions is whether you want to allow his sensibility to take leadership and set the tone for
this if it's going to be a long term relationship.

It might be that your leadership vision is one you'd rather live with and
so that sets the stage for a significant struggle for leadership in your relationship.  Maybe he needs
someone strong in his life.  Maybe you are reluctant to be stronger, just as he is.  That's a very interest
conversation and line of thought, if there is an truth to it.  A lot of women at 50 go there.

YOu might have to end up saying "no, my dear, if we're going to be a partnership, I don't want to make
decisions in this way."

But I think you might be a big reticent to challenge him at that profound a level. I suspect that if you
were more willing, you would have already made more of an issue about staying to sleep and cuddle after making love.
During those cuddle times, spirits intertwine and relationships deepen. When you cut off those opportunities,
you also cut off the deeper levels of growth that make a relationship endure, that give it a foundation. Maybe you are a little
ambivalent yourself.

So what has happened is that you are now calling the whole thing into question. I think that is correct and
perhaps wise. a good change. The message from him, like the going home after making love, is that you can count on him
only up to a point and then he goes away... not to another woman, just back into his private room.  And you accept that, but with more and
more misgivings.

Every relationship needs a bit of separation but there's no rhythm here. It always ends with him going home, or sending you
home (which seems to me even worse). It's extreme.

So maybe,in your mind, you would feel better if you clarify his status in your life because it is distracting your from your ability
to make  those other decisions. Clarifying his status might mean a confrontation and you have to plan it.

This has been complex. YOu might want to
consider having a consultation with me to get a little clearer
but this is a start and probably the best I can do in writing and without

You can reach me at

I hope this helps.

Philip Alan Belove, Ed.D.

[an error occurred while processing this directive]---------- FOLLOW-UP ----------

QUESTION: Dr. Belove,

I believe you captured the essence of his personality very closely.  I can say that he is the most honorable man I have ever dated.  He is in general just a very, very good man.  I have dated some really wild guys that cheated, lied etc and this one is the complete other end of the spectrum.  He is kind, generous, honest, loyal to everyone.  And he truly treats me with such generosity and loving respect.

The spend the night thing has been brought up for discussion a couple of times and he knows that it is perplexing to me.  He knows it is something I want to happen, but even though he knows how I feel about it, he still just simply doesn't do it.  He has told me to stay at his house a couple of times, but only after I said something about it after sex.  It wasn't an actual request on is part for me to stay, nor was it an invitation.  It was rather just in response to thinking I was upset with him and he preferred me not to be upset.  Both times I went ahead home and told him that while I appreciated his saying I could stay, I knew it was not something he planned for happening and I told him I would love to when he actually invites me (or it being his idea/desire).  Neither time did he attempt to talk me out of going home.  It is just so freaking strange to me that we will make love, fall asleep cuddle in one anothers arms sometimes until 2 in the morning.   Then the "bewitching hour" comes and he leaves (if at my house) or the expectation is that I leave if I am at his house.  At one point I refused to have sex at his house.  If we were intimate it had to be at my house.  If he wanted to get up and leave after sex... let him do the driving.  We did that for awhile, but it is hard to plan for when it is going to happen and only be at one or the others home.  

But... it is nothing for the expectation to be that I am driving home at midnight or later!  Even in the freezing cold weather. And it is hard to get out of a nice warm bed and drive home in the cold.

Sometimes I wonder if it fits with the "he doesn't feel like a good provider" issue.  If he can keep that one piece of us at bay, it keeps the relationship from moving toward the next step.  By each of us going home it keeps it more like "dating" and then going home.  Keeps our lives from being completely intertwined.  Since he never seems to be able to give me a complete answer regarding why he won't spend the night, it makes me feel as if this is his way of controlling the pace of the relationship.  Everything is so intertwined, however, this helps keep it from being "all" intertwined.  The one last hurdle to commitment?  and since he doesn't feel that he can be a good provider, he doesn't want to move to the step of feeling that he needs to provide.

As it is.... we get the benefits of being married but we go back to our separate lives where we utilize separate means of providing for our separate homes.

Yes, somewhat our ways of handling things do collide a bit.  He is more of that one day at a time kind ... which sometimes is also a bit of putting things off for today kind of thing.   And I am more of a lets just put it out there and deal with it.  Not wait until it hits us squarely in the face and it becomes an issue.   

You mentioned clarifying his status in my life.  From his mind's eye is that his status is that he isn't going anywhere.  He likes where we are now.  He is very happy with the relationship and feels that it is heading in the right direction and has a good potential for a future.

HOWEVER, for me... all that is fine and dandy except for if he continues to hold a bit of himself back out of fear of not being a good provider.  If he feels we are both better off remaining independent of one another due to that, then it could mean the future never takes shape for us.  Or not for a very long time.  

In the meantime, I again worry about not pursuing career paths that take me away from him only to end up in a relationship that goes no where for years. (if ever)  I am not young... career opportunities get harder as you get older so I hate to lose opportunities waiting for something that never happens.  YET again, I hate to take a job away from here only to mean I am walking away from a chance at a wonderful lifetime with him.

I know how he feels about me, and what he says about the relationship future.  However, there are no guarantees that it will happen. So do I put the rest of my life on hold "in hopes" that it does?

Here is another thing you said, "I suspect it does have a future and could continue as it has for a long time".   Perhaps that is one of my concerns.  What if it continues to be at this level of relationship for a very, very long time and I watch as time slips by but we don't get any closer to the real commitment?   How long is too long to wait for a man to decide he is ready to take that step?

My grown kids have an expression,  "This is how he rolls."  It means, "This is just the kind of person he is ad this is how he does things."

At this point in time you see something very fundamental about him.  Maybe you can't articulate it, but you see it. It's very deep. He's very calm and flexible about it.

"Oh, you want to spend the night?" Well, okay, if you insist. I'll do it because you want it."

It comes down to :"This far and no further."  

Maybe he can't or won't articulate his reasons  either.

You're confounded. You simply would never operate that way.
What is that line he has drawn (and maybe always will draw.)

Maybe he's just revealed his character to you.
This is something you see in people over time, that's stable.
How do you think about someone's character?
That's an important question and the one you are trying ask yourself.
You are trying to make some long term decisions. Job change. Geography change.
And so much of how you proceed rests on how you assess this man's character.
Character is what you believe you can expend of him, stably, over time.
What will he do and how will he deal with things regardless of his mood.
What can you expect from  him regardless of whether you've been at your best and most
diplomatic, or in one of your worst and most childish moments?
What can you utterly depend on?

YOu know a lot already.  And much of what you see you like.
He's kind, not wild, generous, honest, loyal, respectful.
That's all pretty good.
And at some moment,though, he has a limit, and that too
is part of his character.
At some moment he needs to be by himself and will not
sleep with you. He is not interested in merging your lives into one shared

There's no particular indication that he will change.

That's quite a problem for you. It would be for anyone.

I'm reminded of quote from Rabbi who lived about the same time as
the very earliest Christians and it was a great statement about character.

If you are not for yourself, then who will be?
If you are only for yourself, then what are you?
If not now, when?

These are the questions that determine character.
You can apply them to him and to yourself.
How do you answer them?

How do you think he answers them?

Even the business about having you get up and get out of bed and drive home on a winter night seems
relevant but not central. That seems a lot to ask of a lover.
It seems to be a consistent statement about the limits of intimacy.
Maybe related to not being a good provider.
As if to say, "at some point, I must be only for myself."

The more relevant question for you is the third one: If not now, when?

What is clear to you is that you have your limit and you are  approaching it

I suggest that this an unfolding story.
In my experience, people often don't know their character until they are tested.
I suggest you test him.
YOu have to do it in the same soft, generous way he has tested you.

The if not now when question is your guide.
You simple investigate job and geography possibilities as if things
will continue with him indefinitely and, sadly, that will not work for you.

You have reached and impasse with him, although a soft one, but still and impasse.

Act as if, this will not change for ten years and that's too long.  See what other possibilities
there are for you. Look for alternate paths.
let him know, softly, that is this your plan.
Keep him advised. Etc.
Stay as soft and unbudging as he has been.

This should stress him a bit. Allow it. Be kind.

Like that.

Make sense?

Philip Alan Belove, Ed.D.  

Dating at Midlife

All Answers

Answers by Expert:

Ask Experts


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

©2017 All rights reserved.

[an error occurred while processing this directive]