Dating in your 50s

An old friend contacted me with some questions. Some of her single girlfriends had started to date, and their decisions surprised her—especially when it came to sex.

“What’s going on? Is this normal? What’s been your experience?” she asked.


As I listened to her, I was reminded of my earlier assumptions. What I didn’t know about midlife dating, and how surprised I’d been by the changes once I’d found myself single again.

I’ve learned some things I wished I’d known before I started online dating in my 50s.

Finding Myself Single Again

I still remember how awkward it felt setting up my online dating account. A recent widow after years of marriage, I recall looking through my current photos for just the right self-portrait. I wanted to find something striking to use on my newly opened dating profile but saw reams of family photos.

I had no idea what a suitor would prefer—a headshot, a sultry pose, or maybe a full-body picture.


Thinking about such things felt weird and embarrassing. I first had to let the reality sink in that I was no longer married.

Dating is a strange world with its own rules.

Being single again has been a significant change. The last time I had been on a date was back when I was a young 19-year-old. And honestly? I saw little action then, so this has been a new discovery.

I no longer knew the rules or what to expect.

Here are some important questions that helped me get started:

1. Where are the potential candidates?

Meeting single middle-aged men is tough. Outside of dating apps, where do they congregate? It’s not like being on a college campus where nearly every person is unmarried. Are they at the grocery store? Bar? Golf course?


Like it or not, dating apps are the best way to meet an unattached guy.

Ok, so it’s important to open an online dating account. Which one? There’s so many to choose between—Tinder, Match, eHarmony, Bumble, Coffee Meets Bagel, WooHoo, Christian Singles, Elite Singles, OkCupid, Hinge, Plenty of Fish, and so on.

Which one is the best choice?

Each attracts a slightly different crowd. Some are free to use, and others require a paid membership. It took trying several of the online services before I found the one right for me.

Don’t be afraid to experiment.

2. What goes on my dating profile?

The first step is to upload photos. It’s essential to have a mix of images that reflect who you are. Try to use only one or two selfies or closeups. The most attractive profiles feature four to seven pictures.

If you’re like me, this step can be uncomfortable. I’m self-conscious. But here’s the thing, they are going to meet you and me in person. We might as well present an accurate picture of ourselves early on, so there are no surprises.

dating in my 50s2

3. What should I say in the profile description?

I’ve rewritten my profile statement many times. It’s an experiment to see which adjectives and personal information draw the most attention.

I found short, honest descriptions about my personality and lifestyle work the best. Saying something is always better than saying nothing. Don’t leave this section blank. Most online services prefer brief statements, so make every word count.

If you struggle to gain others’ attention, try a fresh set of photos or change your description. Men prioritize the images; women are interested in what men share about themselves.

There are online services that offer help with building your profile if you find this part difficult.

How do I compare to my competition? These fears are usual. You aren’t trying to attract everyone, just the right one!

4. What does the ideal partner want?

You and I will meet all kinds—those enjoying early retirement to the ones in a second career. Some want to start another family, while others have a young family.

Some people are particular about a type of lifestyle or appearance. For instance, I’m allergic to cats. I rule out anyone who shares their home with a feline.

Don’t take these limitations personally. They are not about you, but simply are the other person’s preferences.

I’m a full-figured woman. Not obese, but not skinny. I list this information prominently since most men have strong inclinations about body types. There’s nothing worse than meeting someone who doesn’t know and is disappointed. Be upfront.

Each online dating app tailors its services to a specific group, such as the plus-sized crowd, religious, or professionals. It’s essential to know your audience.

dating in my 50s3

5. Who makes the first move?

After a few months of doing too much waiting for guys to message me, I got bold and created a form letter. Now I send out a short personalized message when I see someone interesting.

Taking the lead may require thick skin for the brush offs and rejections. Expect many of these letters not to be opened. Or, if read, to go unanswered. I’ve learned not to let any of this define me.

Some people will get too friendly too fast. Avoid using terms of endearment, such as “babe,” “sweetie,” or “beautiful” before meeting. Those who do are often scammers or in the sex trade and are trying to build fast rapport so they can hit you and me up for money.


I wasn’t aware of this sad fact when I first started dating and wasted a few weeks texting someone with a fake profile. Now I use an inexpensive online search to run a cursory background check to spot the fraudulent profiles.

Please, no inappropriate photos of body parts. It sends the wrong message. My first dick pic was a shock. It’s not an effective calling card and can be abusive if unwanted.

6. What am I looking for in terms of a relationship?

There are those looking for a hookup, friendship with benefits, or a long-term relationship. It’s critical to know what you want.

Many people are confused about what they’re looking for. Some only want sex, despite claiming differently. Others text and then disappear once the topic of setting up a time to meet comes up.


What is it that you want? Are you ready to embark on pursuing it if you meet the right person? Be sure to give this some thought so that you can be clear about your intentions.

Navigating these uncharted waters feels a lot like wading into a stormy ocean. In the beginning, my ego got hammered until I learned to stay detached and uninvested.

7. What compromises am I willing to make?

It’s been tough to date in my 50s. I have kids, a preferred way of doing things, and a set of friends. Unlike when I was last dated in my late teens, I know who I am and what I want. All of which makes me less malleable.

And so are the men I meet.

What aspect of our lives are we each willing to compromise? Can I become a morning person? Can he? Will I learn to make coffee every day? Do I want to? Am I open to learning what interests him, such as boating or golfing?

What about the kids? Are they supportive? Will they make room for a new person?

Then there’s the social aspect. If we merge household, to whose home? Where do we spend the holidays? What church do we attend? If we go at all, and who decides?

The more you consider what you can compromise and what you can’t, the more likely your dating experience will go well.

8. When does sex enter the picture?

Consider your values and intentions in making that decision. Do you know how to practice safe sex? Are you ready to come prepared should your date be interested?

I warm up slowly to new people and am a person of faith. I’m upfront with those I meet that casual sex won’t be a part of my dating repertoire.

9. The importance of dating with self-integrity.

My newest dating motto is to make decisions that align with who I am. I call it having self-integrity. This means I stay true to myself by listening to what’s matters most to me so that my decisions come from that internal place.

Being aware of these preliminary issues can help us make choices compatible with our values.

Be Patient With Yourself and Those You Meet

I’m glad my friend asked me about what it’s been like to date again. I suspect to an outsider, these issues appear straightforward, maybe even black and white. I can assure you—they’re not.

Stay compassionate, patient, and open-minded with yourself and those you meet. Dating later in life offers another excellent opportunity for personal growth.

Kerry Kerr McAvoy, a psychologist, author and writer, is in cultivating healthy relationships, deconstructing narcissism, and understanding various other mental health-related issues. Her memoir, which explores the devastating impacts of deceit and betrayal, is due out next year.




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