A Strategy for Dating in Your 50s

Navigating the world of dating these days can be completely different than what you knew growing up if you haven’t been in the ‘game’ for a while.

So, you’ve been married for 20–30 years and it all came to head. You’re still young and can’t see yourself spending the next 30–50 years alone. You’ve been working on yourself for a while and now you’re ready to start dating again… Now what?

In 2017, I found myself in this situation as well. After being married for 20+ years, I was first faced with the dilemma of, “am I ready to date again” or “do I really want to date again?” I took a few months to start writing and journaling and really get some perspective on who I was, who I wanted to be and, what I would be looking for if I was to start dating again.

“I worry that my Soulmate is on a different dating site…”

My foray into finding out what kind of options I had, as far as dating goes, had many friends suggest I try some dating sites. Apparently, this is how it’s done now. Coming from an age where meeting and finding the courage to talk to a woman got you a date or, a phone number, I had no clue that people were just window shopping for their next partner on different platforms online. At first, it sounds as simple as picking out a ripe fruit at the market. A simple right or left swipe let someone know you’d be interested in them, or not. It seems all too shallow to me as, I don’t think of myself as a photogenic person to start with. I didn’t like the idea that my humour, communication skills and any other things that had helped me get that first date in the past would hardly help me in meeting someone if I didn’t look great. I certainly wasn’t going to ‘touch up’ my pictures either.

I’m going to get right to the point here and say that I had very limited success with online dating. Sure, there were plenty of nice women and I had lovely conversations with many of them. One of my issues was that many of the women I was attracted to and, had most of the qualities I was looking for were far away, sometimes an 8 hour drive away. That may be fine for some people but, building a relationship online, talking for months on the phone and texting, wasn’t my idea of how to develop something naturally. Call me ‘old school’ but, I wanted something a little more organic and something I was comfortable with. Besides, with a full time job and a not quite empty nest, travelling hours to meet someone just wasn’t what I was looking for.

In the last four years, I’ve had several first dates. My first one was a blind date. It went well but didn’t go anywhere. I was just dipping my toes in to see if I felt ready for the dating scene. I was surprisingly ready to date much sooner than the articles I read led me to believe I would be. I imagine that, at this age, we recognize that our time on this marble is limited and it’s to our benefit to move on quicker and just accept change. It didn’t take me long to meet my next first date. I met this woman that I’d gone to school with. We bumped into each other three times within a week and figured it was the Universe sending us a clear message that we should make our bump-ins less random. I found her that night on a social networking site (FB) and just struck up a conversation with her.

“Never stop learning, because the world never stops teaching.”

My skills in texting someone are very limited so, I wanted to play to my strengths as much as possible. Within a day, I suggested that we meet and have a drink. One drink turned into two. Next thing I knew, we were making plans for dinner! Fast forward two months and, things didn’t work out. I guessed that the Universe had been telling me a different message than I thought. I did, however, keep in mind that I was able to get that first date with only minimal texting skills and quickly converting that to an actual meeting to see if there would be some chemistry. It’s strange to me that, in a world of social media, I’m much more comfortable in a face-to-face setting. Maybe it has to do with being in sales for much of my life but, I would much prefer to meet someone in person and develop things naturally than to try and build an artificial relationship via the net or 5G. I’ve also had terrible luck in one of those artificial relationships but, that’s a different story.

“Be yourself; Everyone else is already taken.” — Oscar Wilde

One of the major points I want to make is that we should all stick to our strengths. I didn’t like the idea of online dating and, I eventually met someone that disliked it as much as I did! I tried a dating site for a week and, She saw me there. She didn’t do anything about it at the time though and, I lost interest after a week of searching for Her. Her profile was invisible anyway so, it’s like we were looking for each other in the dark. When her own lack of success led her to take a second look at me, she found that I was no longer on the site. My biggest success with online dating is that I always used my real first name on it. The reason that helped me so much, is that she was able to remember it and proceeded to search for me in our little town on a little known site called FB. You can do whatever you want but, I never would have met her, had I used a fake name. Having an uncommon name, she found me quite easily and sent me a friend request.

One thing I came to realize over the last few years is that, you will have to develop some kind of skill with building rapport via messaging or texting. With however many crazy people are out there, people are constantly screening who they want to date and, they won’t give out their real information until they feel that you don’t fit into that crazy, toxic category. So, I learned to put my best foot forward and just jumped in. Don’t be scared here. This is mostly a weeding process that you’ll both use to determine if they/you get to the next step and phone numbers get exchanged. Once that’s out of the way, you can start getting to know each other a little bit. I don’t trust too much what people say on their messages, having had a terrible experience before. That’s why I like to keep things light and very soon, suggest we meet somewhere for a drink or something just as safe.

“And you smiled, and I wondered if I would ever think of anything else.” A.R. Asher

So, She met me for drinks a couple days later. We put this online dating, texting and messaging behind us and just let things happen the way they would have 30 years ago… Naturally. She had so many qualities that could never be conveyed online. Her voice, her laugh, her smile, her wit… I fell for all of them. A few months later and I’m still as enamoured with her (way more if I’m 100% honest)as our first date.

So, stick to what you feel are your strengths but, know this: Things have changed and dating in your 50s (or older) means you might actually have to learn some new skills if you’re looking at dating seriously. Whether you like it or not, finding your next or last first date, will more than likely involve some form of online communication.