Relationships | Later Life Dating

Online Dating in Your Fifties — Can It Really Work?

What led me to meet someone again

Loneliness can eat away at the heart.

Slowly and unnoticed.

Till it is too late.

You are left with a shriveled heart.

And a blanket of emptiness wrapped around you.

When I tried online dating six months ago, it did not go well. I came away from the experience, wondering if the blanket of loneliness would threaten to cover not just my shoulders but my whole body.

I took a break from online dating. And did some self-work taking time to consider what it was that I was truly looking for.

Did I even want a relationship?

And if so, what was I looking for in a relationship?

I was so set in my own ways. I hadn’t been in a relationship for 10 years. I know! I accepted, therefore, that there would be areas I would need to settle on. So, what were my compromises?

I knew that dating in my fifties or more was going to be a case of wrenching that blanket away sharply and swiftly before it became even more entrenched. The alternative would be spending the next ten years alone.

Here’s What You Need to Consider When Dating in Your 50s

Physical attraction

Do looks still matter later in life?

Many of the profiles had balding men. That’s fine if you are attracted to balding men. I never used to be, but I had to be realistic here. Most men reaching this age group are starting to thin and bald on top. Compromise.

I also had to consider my own looks. My twenty-year-old figure had long left my body. My belly had been taken over by the menopause and looked like I had swallowed a whole chicken which hadn’t been digested yet.

My hair was thinning with streaks of grey highlighting it. My neck was starting to show signs of wrinkles. My teeth were no longer straight, I’ve even lost a few. (Thanks, Covid and no dentists seeing anyone!!)

I had to be realistic. At a basic level, there does need to be some physical attraction. But I also realize that we would be more, let’s say ripened and matured in our later years.

I set my age bracket at 57–62. And the search began.

Commonality

It was important that we had similar values. A similar educational background. Or at least someone who could hold a provoking conversation. Share views. Opinions. And maybe has similar aspirations for this stage of life.

I wanted someone for whom family remains essential. My girls and grandkids, still come first. They always will.

I would expect that in this age group, most men who had children would either have grown-up children, maybe even a few grandkids, so would align with these aspects.

Some similar interests always help to break the ice. But some differences allow space to do our own thing. It would be a bonus if they liked walking, travelling and sharing laughter. A sense of humor, I felt, was an essential quality.

Am I asking too much?

Stability With Fun

I wanted someone who was stable. Comfortable in their own skin. Someone who was already happy in their own company but meeting someone would add to their life.

I expected that someone in my age bracket already had their own patterns, hell, I was well set in my ways, so how would our ways fit in together? But I also needed someone ready to step out of their comfort zone and share new moments in life together.

I wanted to holiday together. Have meals out, just because. Walks. Holding hands. Hugs. Being touched. Doing something on the spur of the moment because we could.

So, I scoured the profiles for a match of these areas of interest.

Family and Friend's Reactions

Before I went any further though, I shared my plans with those closest to me. Their views are important; you need them as part of your safety plan too.

My sister was thrilled that I decided to try dating again. She had been asking me for years when I would try to meet someone again. I had never felt the need before.

It was a big step not just for me, but also for my daughters, even though they are adults now. My oldest daughter had not coped well when I last dated, she was 15 at the time. Let’s just say she did not make it easy. Now that she is as many years wiser, she has already said she will give him more of a chance and apologised about her 15-year-old self.

I had put thoughts of dating aside over the years, as I had wanted to see my youngest daughter settled, I walked her down the aisle recently.

My friends were over the moon and plan to vet him at the earliest opportunity.

Now I just needed to find him.

How My Online Dating Search Unfolds

One day in late July, I re-opened my subscription to the Ourtime dating website.

I decided to go for the 3-month subscription, as I was serious that I wanted to spend time looking and not feel under pressure of a week’s trial or a month’s subscription. I was not in a rush and was happy to chat with people and see if the connection was there.

It was, therefore, easy to get started again. My profile was up and all set already.

Very soon I was chatting. I spoke to three men in turn.

Guy # 1

The chat died off after a couple of messages.

Guy # 2

Same vibe.

Guy # 3

A week later we were still chatting. And chatting. And more chatting. We planned to meet for a coffee.

First Date

It was a rainy day, and he agreed to come my way, so I didn’t have to travel. We met in the town centre in a public place, like you are advised to do. Safety factors still count at every stage of life.

He was standing waiting and had brought a spare umbrella, in case I didn’t have one with me. Pretty thoughtful, I hadn’t given it a thought, him standing and waiting for me in the rain. 🤦🏽‍♀️

We had a coffee which turned into a meal and then a long chat when he realized that his car parking had run out. So, the date came to an abrupt end with him rushing off. We both agreed that we would like to meet again.

Second Date

He wanted to show me where he goes open water swimming. I don’t like swimming, but I agreed to meet, as it is a public space, with a café with plans for a coffee. There was also a private car park attached.

We had a long walk and sat overlooking some hills and chatted. And chatted. And laughed. And it felt like I had met an old friend and we were picking up from where we left off.

Then his phone rang. It was the owner of the café, letting him know that they were closing up, and the car park would be locked shortly. Neither of us had noticed the time. It was a crazy rush down the hill to get back.

I was hot and flustered and did not look my best by the time we arrived back down. He offered to buy me dinner. He felt so bad about the ending. So, we did. And we laughed about the event. Chatted. And neither wanted the evening to end.

Third date

I agreed to meet him in a public space, and then he drove us to a walk he knew. When we arrived, the car park was closed. We both looked at each other and burst out laughing.

We certainly weren’t having much luck with car parks.

We changed plans and went on an alternative walk. His hand slipped into mine, and we walked hand in hand. If anyone saw us they would think we had been together for years.

It all felt so natural. So easy.

We didn’t have to pretend who we were not. We were able to be ourselves.

When you date in your 50’s there’s no time to play games, you either like each other and want to see where it takes you.

So that’s what we are going to do. We will see where this takes us.

And hope that we have no more car parking traumas.

Wish me luck. And that the blanket of emptiness has finally left my shoulders.

© Bernie Pullen, All Rights Reserved