Dating at Midlife/Flirting at our age


QUESTION: Hi Dr. Belove,

When is it normal or acceptable for a person in long term relationship to flirt? When in a relationship is it harmful? Is jealousy ever an appropriate emotion in response? Are some people just natural flirts and if so when do you know if it means something and when does it not?

My boyfriend is what I would call an inveterate flirt. He has kissed another woman while in a  relationship with me. It was an old girlfriend of his and he made out with her after a funeral. He sent a completely flirtatious email to a co-worker indicating that she turned him on because she was pregnant. He asked her if that was okay? I saw the email when I was working on his computer and yes I know I should not have read it. He makes eyes at other women in public. I would not have read it but the kissing thing hurt me so much that I snooped.

I have never been jealous in a relationship before this but now I am. At 55 years old and after many years of living together. I don't trust him. He says I have to but I don't. In church after biting my head off for asking him to put his arm around me because I was cold, he went and held hands with some woman I had never met during the meet and greet section. Did not introduce me either. Yelled at me later and said that should be okay because he has known her for years.

He says I am wrong to be jealous. I respect you immensely. I would like to know what you think. I say he lacks respect for me.

ANSWER: Hi, Again.
I've been thinking about my answer and I think it's  incomplete.
The basic idea of my work is "reading and righting relationships."  The idea is that if
you can read the relationship, then you can shift it to where it's more how you want  it.  You can shift the relationship, not the person. Although people do have slightly different  personalities depending on how the relationship is going. But mainly you're reading the relationship.

so,even though everything I told you below is still true, I think, it's incomplete.

I think the key question is this: why would this guy endanger a  perfectly good relationship by insisting on flirting?

Since it gets a big reaction from you, and since the guy isn't  a bad person, then why is he doing what he's doing?  This is a fair question.

Is what he's doing a comment on the relationships you guys have with each other?

You are reading it as if it is.  In your  reading of things, it's like he's getting at this sexual excitement elsewhere.  

Well, you should never have only one theory for someone's motives...including your own.  

What do you think he's trying to tell you?  Look past your jealousy and see if you can answer that questions.  Maybe your jealousy is a correct intuition of the relationship status.  

Is he getting bored?  Not enough sexual excitement?  and if so why?
Is he trying to figure out something about his attractiveness as a man?
Is he trying to figure out something about sex?

I think to answer this question you'd have to review some of your conversations with him and some of his stories about his past.  Possibly if you could figure out what he's doing, then you might be able to shift it.  

All of this doesn't discount what I wrote earlier, it just enlarges it.  I think I wanted to show you a few constructive ways to approach this relationship challenge.
Hope this is helpful

Hi Ann,
Good questions. Thanks for the chance to answer.

Jealousy is a natural and normal emotion.

You are not "wrong" to be jealous.  It might be that he doesn't want to deal with your jealousy, or that he doesn't respect the fact that you are jealous. But that doesn't mean you are "wrong." It just means that You (plural)  have a problem. It's his problem as much as it is yours.

What you will need to do is find a way that makes this clear, that it's his problem as much as yours. Right now, he is  trying to push it all back on you. That really won't work.

So far he is saying to you that he doesn't care about your feelings, or he resents your feelings, or he's not going to change his behavior just because it bothers you.

He has taken a stand, and perhaps not very thoughtfully.  

Now this is a difficult position for you.  On the one hand, it makes you very hurt and very angry. It is so disturbing to you that you are sorely tempted to call the whole relationship into question. "Deal Breaker" time.

Now, about whether it's "okay" to flirt.

So much depends on what you mean by "flirt."  

Is it okay to tell something of the other sex that she (he)  is marvelous and sexy and attractive?
I think  it is.
I told that to my daughter often when she was a teenager. I said she was gorgeous and beautiful and smart and fun and fabulous.  I was not flirting with her.

Flirting is more about inviting someone  into a kind of dance that could go somewhere.  If you are really in a relationship already, and you have an agreement that the relationship is monogamous, then flirting isn't okay because flirting says, "I'm available for something if you are available for something."  That's either a lie to the new person (because you're not available), or confusing to the new person( "Is he available? What is he saying?) or a betrayal to the partner ("I know I said I'd be true to you but I'm flirting with, playing with the idea of, possibly, not being true to you.")  

We could be generous toward him and say that maybe he hasn't thought  this thing through. Or maybe he has some ill-understood compulsion to fool around like this. Or maybe he has no idea what it means to really connect with a partner.  But still, it's very unpleasant for you and you will leave him eventually if he keeps it up.

What do you think?

Philip Alan Belove, Ed.D.

---------- FOLLOW-UP ----------

QUESTION: Hi Philip,

Thanks so much for your thoughtful words. How do I get him to see that it is our problem and not just mine? He is absolutely resolute in the fact that it is all my problem and that he is not flirting but just being friendly. I really need some help with how I get him to discuss and understand the idea of a shared problem.

I do not think he is sexually bored as he has told me that we have the best and most frequent sex he has ever had. He seems happy there. No, I think he is looking for something I am not able to provide. Validation from many women that he is still sexy at age 62 perhaps. I would also say that he is not completely invested in our relationship and is looking elsewhere but is not willing to let me go. That is truthfully how it feels. He is putting out feelers. Like I am good for him but not good enough.

Maybe he cannot really connect with a partner and I am just wasting my time. His ex-wife says he was the same way with her.Never able to give up other women he was with in the past and always longing for a new connection but he does not have sex with these other women. I guess he can tell himself he is not cheating that way.

I will eventually leave. It hurts too much to stay.

We're on the right track.
You've asked the right question.
The thing to do here is stay measured and not get sucked into reactions.  This will require a higher level of self mastery than you might be used to so don't underestimate the difficulty.  
YOu have to think about tone and content, how you say it and what you say.  The tone has to be soft and measured because the content will be explosive.  This will be a strong confrontation and you want to support him so he can handle what you are going to say and so he can think and not just react.  

Here is a script for you:
:Dear one,
when you say it is "my problem and not our problem," I get scared and upset and I will explain  why.

If we are together, then it's "our problem."  If there is something in this relationship that makes me very unhappy or hurts my feelings... or something, say I do, that hurts you,  It's our problem.

The only way it would be "my problem" only would be if I leave the relationship.  
THen, okay, I can say, "I had a problem" and you can say "she had a problem."  And so we ended the relationship.  
but I don't want to end this relationship

and so that's why it has to be "our problem."   when it's "our problem,"  then we are working together to make this relationship work for both of us.  
When you say it's "My problem," then it sounds like you don't care about how difficult this is for me. It sounds like you're telling me you don't care anymore.

This puts me in a difficult position.  Can you understand that?

Maybe this is just what happens when we argue and things escalate, but it is a serious issue and I
don't want it to be the end of what we have."

So that's the idea.  Now he might get really bothered.  In that case, stay calm and say, I know this is difficult but we have to think about it.  I can wait or a day or two or even a week, but I wanted you to know my thinking on the matter.  

What I want is for you to acknowledge that this issue is a relationship issue and as much your problem as it is mine. "

Now your problems is that you have to be willing to really listen. You have to be willing to listen as well as you want him to listen.

So all that should set you both up for a fairly difficult intimate conversation.  

Let me know what you think and whether you want more direct coaching on this.

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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