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Smart Dating Over 60

Mature dating advice to find true love after 60, from both a senior woman's and a senior man's perspective.

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About Cosmo

Until recently, my struggle with dating and relationships felt like an unsolvable mystery. After many years of floundering, I had resigned myself to a “men are from Mars, women from Venus” situation. But unlike the book of the same name, it seemed that communication was impossible and the two sides would never meet.

Yet despite this false acceptance, the thought of finding a good relationship continued to frustrate me because I always had the nagging suspicion that there was indeed a solution. As a baby boomer, I saw plenty of people my age in happy, romantic marriages and relationships. Those who were dating always seemed to be adept at it.

mystery of dating as a baby boomerSuccess at Everything—Except Romance

Looking back at my life, I always excelled at school and was a good performer at work. I did even better when I started my own small business and met with incredible success.

Even though I was good at finding solutions to almost everything else in life, for some reason I had missed the solution on how to have a good relationship.

How could that be? What was I missing?

Here I was, in my mid-50’s, ashamed to admit that I had not one, but two failed marriages. Dating again just didn’t seem wise. And even though I lived alone, I was never lonely. I had plenty to keep me occupied and relatively happy.

Clinging to Hope for Dating Success

Yet I still felt a longing for companionship and romance. I still had a hope that there was, possibly, someone out there who could share life with me. At times I wondered if this was merely a fantasy that stemmed from childhood.

As a kid, I loved watching Disney movies and popular TV shows like The Brady Bunch or The Waltons. What appealed to me was their portrayal of happy families. My home was the antithesis of the serene, joyful, and happy homes I saw on television.

I lived in an alcoholic household that was an endless cycle of violence, abuse, fear, and uncertainty. It was a nightmarish existence from which I couldn’t awake. The TV family shows helped me escape for a while and offered some hope, however fantastic.

So, I clung to this hope even into my post-marriage bachelor days. Following a couple years of single life, I reluctantly eased into a relationship. I knew her from church and we had some things in common. It was also nice to have lunch or dinner with someone without being the third wheel.

Ending the Troubled Relationship Cycle

But from the second date onward, I ignored emotional warning flags about the relationship. As with my marriages, I stubbornly plowed on, thinking I could work through or overlook these problem areas. I even told myself that perhaps these problem areas were a sign of something wrong with me.

My therapist later said I was loyal to a fault and this latest relationship was no exception. After more than four years of sweeping things under the carpet, I ended it.

I was sick and tired of repeating the same emotional mistakes despite the best of intentions. At this point I was convinced it was better to be a bachelor to the end of my days. I didn’t have the strength to try again but at the very least, I wanted to find out why I was so bad at this! That’s when the therapist entered the scene.

Simple Truths Lead to a Solution

To my surprise and with the help of my therapist, I uncovered a simple truth about why my relationships failed. With the remarkable clarity of hindsight, it was easy to see how and why I repeated the same scenario.

With this new-found knowledge and several months into the single life, I felt strong enough to try dating once again. I had learned how to recognize relationship warning signs and most importantly, how to listen to them.

I also found that my career in marketing and sales gave me great tools to use in the dating world. I spent time crafting my “message” for an online profile. I spent time figuring out the type of partner I really needed and wanted. I spent time ensuring that I could stand on my own two feet emotionally, so that I’d be ready to stand next to a new partner.

A Great First Date, True Romance, and an Authentic Relationship

In no time at all, I met Daisy on an online dating site. By the second date we both knew the relationship was going somewhere great. Today, we have a loving, joyous, committed partnership that is truly beyond what I had ever hoped for.

That’s why we both decided to create SmartDatingOver60.com. We want to share with you the story of how we got here, of how we easily found our ideal partner in each other.

I think those of us over 60 who find ourselves thrust back into the dating world have our own special perspectives and needs. Daisy and I plan to address them because we’ve been there. We’ve experienced the anxiety and trepidation as well as the fun and rewards of dating after decades away from it. And we’ve done it at a time in our lives when we thought dating would have been a distant, fond memory.

You can read more about our story in the blog articles listed at the right. Search by category, or start by reading recent posts.

In these we share some simple techniques to help you find the right partner, and to do it faster than you thought possible.

By the way, Daisy and I both use pen names on this site (Daisy Drake and Cosmo Wright) so we can share the specifics – and sometimes intimate details – of our individual dating experiences . . . from both a woman’s and a man’s point of view.

Using pen names, we can reveal more about ourselves and the people we’ve dated and had relationships with, while protecting their identities. Because we can talk more freely through our alter egos, you’ll get more of the authentic over 60 dating experience.

Never Give Up on Finding True Love.

Our message is one of hope, to never give up on the dream of an awesome, loving, fulfilling and romantic relationship.

As I’ve discovered, true love is not a childhood fantasy. It’s a dream that can come true.

We hope we can help you on that journey to finding your ideal partner!

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