Fewer fish in the 'boomer' dating pool

by Toni Coleman, LCSW, CMC

Dear Toni: I am a 50-something, twice married but presently single female. My first marriage lasted 22 years and produced 3 children who are now grown. Their father was a very supportive partner in many ways, but he was completely irresponsible and could not — would not — hold down a job, pay a bill, or balance the checkbook even though he was a college graduate and came from a privleged background.

After years of working part time, existing from paycheck to paycheck, struggling just to make ends meet, and dealing with escalating anger and conflict, I told him it was over. At that time I had been communicating with an old love and we began to see each other during that year of separation and for a time after the divorce. 

That didn’t work out because I realized he was not the person I had once believed him to be and I just didn’t feel the same way about him anymore. Approximately 4 to 5 years after my first marriage, I tried online dating and found that almost none of the men interested me. But it wasn’t long before I was contacted by someone who was attractive and sparked my interest.

We went quickly from emailing to the first phone call during which we talked over 5 hours. He had the most wonderful voice and I found him to be funny, articulate and very easy to talk to. He also had his own business, owned his home and appeared to be a hard worker and very responsible with his money. Soon afterwards we met and after only a couple of months, we got engaged. I realize now that was much too fast but at the time, it felt like the right decision.

Fast forward to the present. We were married for about 4 years and most of the time it was awful. Two weeks after the wedding, I spent a miserable weekend in tears at my daughter’s college graduation and it was because I knew I had made a terrible mistake. He was emotionally and verbally abusive, completely incapable of warmth and empathy, and after only a couple of months, he was hardly working at all. In other words, I was either completely blind to who he was, or he changed after marriage.

It took getting separated, off and on marital counseling, and even going through with the divorce before I could make the decision to finally end it. I felt like a “two time loser,” and it kept me from getting out sooner, which would have left me and my life in better shape.

After it was all over, my finances and overall life were in shambles. I have been single for three years and it has been a struggle. I went back to online dating and have met two men I began to get serious with. I even thought one could be the love of my life. However after months of emailing and many conversations, we spent three days together — it was clear he was not at all the person he had presented himself to be. I quickly ended it and I’m now wondering if it’s even possible to meet someone who has it together and is available at this stage of life.

I know this letter has been long, but I thought the background would be important in order for you to understand where I am coming from in my (following) questions. Where are all the normal, good guys? Is it even realistic to think that quality, single older men can be found on dating websites? How can I know if a guy I meet is who he appears to be? Any insights or feedback would be greatly appreciated.                                                 

Signed: Seeking One Good Man


Dear: Seeking One Good Man:

Would you be surprised to know that your situation is not that unique? There are many older, divorced women out there who have become very discouraged by their online dating experiences. Yes, there are those who get lucky and meet their "right someone" quickly and somewhat effortlessly, and others who, with persistence, eventually find suitable mates.

However, in my experience, the older a woman is, the harder it can be to find the right partner online due, in part, to the ratio of women-to-men and also to other lifestyle issues that impact dating more for older people.

Therefore, while I plan to answer your questions, I want to also suggest that you add one to the list: “What can I do differently this time around to increase the probability I will meet and connect with the kind of men I seek?” Apply this in a very broad context — not just using different ways to approach and handle online dating but also finding novel ways to meet and connect with the kind of men you are looking for.

Let’s begin with a brief snapshot of your relationship history. You have been married to two men who were quite different from one another — yet neither relationship offered you what you needed. Your first had many qualities that you appreciated, yet life with him left you handling all the financial and other family responsibilities.

It appears that your attraction to number two may have been in large part because he seemed so different from number one. Yet it sounds as though the marriage was less happy than your first and ended much sooner. What we can draw from this assessment and comparison is that you didn’t approach your second marriage (maybe not the first, either?) with a clear understanding of what it was you wanted and needed in a partner, some of your decision-making was based on avoidance rather than conscious choosing, and you acted impulsively and possibly from insecurity and/or your own unmet needs.

It’s important to look at yourself first because you are the common denominator, here. This means that the kind of men you are attracted to; their qualities, values and overall attributes, and how quickly you move into commitment can offer you important information about why your past relationships didn’t work out and how you could do it differently this time.

This is relationship readiness and I recommend that you do some work here, first, before jumping back into the dating pool. Once you have a better handle on yourself and what you want and need in a future relationship, you will be ready to write a profile that attracts your right type, and you will be much better at spotting and eliminating the wrong for you guys upfront.

This actually addresses your third question that asks how you can know if a guy is the person he presents himself to be. Once you know what you are looking for, don’t limit yourself to online dating. Spend some time thinking about where your type of man would go, what he would be interested in, and how he would spend his time. Consider everything from clubs, to sports (as both a player and as a spectator), to the arts and volunteer opportunities. Spend some time brainstorming and then going online to find the best local resources.

If you have a passion — pursue it. This is a great way to meet someone with whom you share at least one important interest. Now I can addrees your other two questions. Normal, good guys are all around you but if you aren’t in the right place and time to make a connection and you don’t recognize him when you do meet, it will just be a lost opportunity that will reinforce your belief that there are no avaialble good men out there.

Older quality single men can be found everywhere, even online. But they are in short supply  and get snapped up fast. If you want to increase your probability of online dating success, you will have to check the site frequently, email someone immediately when you feel an interest and suggest you have that first face-to-face meeting sooner rather than later.

The last piece of advice I will offer is to move towards commitment deliberately and consciously. Rushing into anything could cost you a lot more time, potential happiness, and peace of mind if you find yourself, once again, with the wrong guy.


Toni Colman, LCSW, CMC is an internationally known psychotherapist, relationship coach, and founder of Consum-mate, a successful coaching practice that provides singles with the help and advice they need to achieve lasting, healthy relationships. Our focus is on singles who are in need of help with such areas as relationship readiness, problems with intimacy, meeting and dating difficulties and other issues that create blocks to healthy relationship building.  Toni also coaches a number of married individuals who are seeking to improve or enhance their marital relationships. www.consum-mate.com.

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