The Challenges of Re-entering the Dating World When You are Older

I never anticipated that I would be in my 60s and dating. I got married in 1973 at the ripe old age of 22.  But in 2009, at the age of 58, I joined the ranks of single women.

The first three years of my singleness I truly did not consider dating. I knew I had too much emotional baggage and I spent that time trying to repair myself. But by 2012, I was getting a bit restless about my single life. I would tell my friends “I am thinking about thinking about dating”.

It is funny but what I missed the most were the simple acts of companionship. I missed quiet conversations over a glass of wine at dinner; the physical touching that is not sexual in nature but is still very intimate such as holding of hands and patting someone’s arm; I missed the sharing of memories and family stories; the comfortable silence that occurs when you are emotionally connected to someone…..such as being together while reading the newspaper and having a cup of coffee.

And certainly, to be honest, I missed the adult physical intimacy that occurs when you love someone and are committed totally to him. But to regain and find such a relationship means one has to be willing to date…. you cannot go from single status to being a married or a committed woman without dating.

But where to start? And what do you do?  And what are the rules for dating in your 60s and how can you find out about them? You can read magazine articles and, in the new world of technology, read articles on the internet using the ultimate search tool….i.e. Google.

But do you have any idea what appears when you Google topics such as “dating in your 60s”??  The advice was endless and overwhelming and, at times, just plain intimidating!!! (I am sure I am permanently marked forever in the Google Database as a “clueless older woman lookin’ for love.”)

And how do you meet someone to go out with?  Statistics told me that there were a lot more women than men and that the men my age were looking for a much younger woman. I would attend church events or events at work and smile and be gracious. But there were no follow-up phone calls or emails.

Then, there are the joys of on-line dating. I will confess that I would get as far as looking at the introduction page and sometimes you could view (without signing up) a few pictures of some of the possible prospects. In the on-line dating world, you create a “profile” and a “handle”.

Some men were obviously trying to create a handle that played off their first name such as the “Ben Waiting for You” or “The ART of Loving You” …… and the pictures they would post—such as the older man with a beard wearing a Superman shirt. Really??? Is that the best you can do??? I would see the pictures and read their handles and would decide to quickly turn off the computer and go to bed and pull the covers over my head.

And there is the issue of baggage—when you are dating in your 20s, your baggage is the size of a carry-on suitcase. At my age, you might need a luggage cart for all the baggage. And you realize that many of the things you enjoy were done in the past with a previous spouse or partner.  Would I be able to deal with past lives? Would he?

In my 20s, I would worry about how long should I wait until I called my date back….if I called him at all as in my era women did not call men!!!  In my 60s, I had to worry about how long should I wait until I email or text him back. Should I add any xxxs  or ooos to the email or just a smiley face? And just what kind of Smiley Face—should I use the one that is blowing a kiss or is winking or just a plain ol’ Smiley Face?


Yet, in spite of all the concerns, there are some good things about dating when you are older (as in your 60s.) I have a clearer idea of who I am and what I want in a relationship. I am less likely to put up with a bunch of hooey but at the same time, I am more tolerant of flaws/personality quirks. I let some things roll off my shoulders as I know, in the big scheme of things, it is not important. I have a deeper understanding of what is really important to me.

Dating when you are older is both fun and scary… and there are risks… such as the risk of getting emotionally hurt …. But if you are willing to take risks….  And if you meet someone and you are willing to work at creating a truly meaningful relationship, you also may be lucky enough to find a deep and lasting companionship… one where you share laughter and smiles.

I shared in the October 2013 post my story about the Gentleman Caller with Smiling Eyes (GCSE) ….. how we met….. our first “pre-date” which did not go very well….. and the “divine intervention email” that led to our meeting again.

I will have to confess that when the GCSE entered my life, I threw up roadblocks for months….. and gave him a lot of reasons as to why I was not willing to get serious. He told me that he was a patient man. And slowly but surely, after many months….. I realized that I laughed all the time when I was with him; that I was comfortable with him; that he was caring and kind; he was generous; and he liked to do a lot of different things from hiking to museum visits to wine tasting events to watching sports on TV.

And I came to realize that the things I missed such as quiet conversations over glasses of wine and comfortable silences….. those things had magically reappeared in my life.

He has never been officially identified on this blog as anyone other than the Gentlemen Caller with Smiling Eyes. Nor have I ever posted pictures of us on this blog. But after two years of dating, it is time for that to change.

His name is Don…. And his presence has filled my very ordinary life with great joy.


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