Things No One Warned Me About Dating in My 50s

Dating in my 50s

An old friend contacted me with some questions about what’s like to be dating in my 50s, as some of her single girlfriends had started to do the same, and their decisions were surprising her — particularly when it came to sex. Since she was still married to her college sweetheart, this was unknown territory.

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

Listening to her reminded me of the earlier assumptions I had had. 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 encountered unexpected complexity as I sorted out challenging questions.

Finding myself dating in my 50s

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 an attractive 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. Even wrong. 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 big adjustment. The last time I had been on a date was back when I was a young 19-year-old. And honestly? I hadn’t seen much action then, so it was all new to me.

Looking for the right profile photo has been one of the most straightforward steps I would take as I began to date again. I no longer knew the rules or what to expect. I hoped to figure it out enough to find companionship, maybe even marriage.

Where are potential candidates?

Meeting single middle-aged men is tough  Outside of dating apps, where can I meet them? It’s not like being on a college campus where nearly every person is unmarried. Are they at the grocery store? Bar? Golf course? Not likely. And how can I recognize them? There’s no secret signal or handshake. Glancing at every guy’s ring finger is hard work, and even then not a reliable indicator he’s available. And I don’t have friends who know a few single men they’d like to set up.

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

What do I put on my dating profile?

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 Meet Bagel, WooHoo, Christian Singles, Elite Singles, OkCupid, Hinge, Plenty of Fish, and so on.

Which one is right for me?

And then, how do I prepare a profile? What do I say about myself?

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

How do I compare to my competition? What do the other women’s profiles look like? Do I have enough photos of the right type? Have I done enough to set myself apart from the field of available women?

What do men want when dating in the 50s?

After crossing the hurdle of preparing my dating profile, I hit the next obstacle of reading through the available men’s information.

Thumbing through many profile descriptions, I’ve discovered I’m often not the type the average guy is looking for. Some want to start a second family. Well, that’s not happening.

Then others have a young family. Do I want to enter that world again with the complication of dealing with someone else’s kids?

Some men are very particular about appearance. Their profile usually reads like this, “I work hard to be physically fit; I deserve someone who takes care of herself too.” Really? My plus-sized body is a sign I’m not taking care of myself?

I’ve earned this beautiful female shape. I’ve given birth to three children and worked hard all those years, tending a career and caring for my family. Motherhood has changed me. And that’s not good enough for these guys? Sorry, buddy, but I deserve someone better too.

So now I know my curvy body is an issue with some men. This, of course, varies on the pool of guys drawn by that particular app. Some dating apps are tailored to the plus-size crowd, others to professionals, and then there are those for the religious among us. If I want to get my profile in front of different groups of men I will have to spend more money to open several dating accounts. Frustrating, expensive, and time-consuming.

Who makes the first move?

Then there is the issue of who makes the first move: him or me?

After my first few months of doing too much waiting for a guy to message me on an app, I got bold and created a form letter. I made sure to personalize it before sending it to someone I’d found interesting.

Taking the lead requires I grow some thick skin for the brush offs and rejections. Many of these letters never get opened. Or if read, goes unanswered. All of this hurts at first until I learned not to let it define me.

Some men overwhelm me with sweet nothings, acting as if we have known each other for years. Often these are fake profilers who are trying to build fast rapport so they can hit me up for money. I didn’t know that in the beginning. After wasting a few weeks texting a guy or two, I soon opened an account that allowed me to run a cursory background check so I could spot the scammers.

My first dick pic was a shock. I still remember the sensation of being hit with icy cold water when I opened that unsolicited note and saw a fleshy-colored photo of a strange man’s appendage.

“Like what you see?” he texted.

That’s supposed to be an effective calling card? I flushed beat red as I typed back, “Not really.”

All these issues cropped up as I set up a profile and began to swipe right and left. And I hadn’t even had my first date.

What am I looking for in terms of a relationship?

Then there’s the issue of what I’m looking for in a potential match. Do I say I want to marry again? My candidate pool is already pretty slim. Will I shrink it too much by being that forward? Or is it better to say I want an LTR, Long Term Relationship?

I’ve discovered the men on these apps are equally confused. Some only want sex, despite saying differently. Others text and then disappear once the topic of setting up a time to meet comes up. There are the players who are managing multiple relationships they may or may not tell me about, the married ones who are looking for extracurricular activity, and commitment-phobic guys who have never been married and probably never will.

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 until I met someone equally ready.

What concessions am I willing to make?

It’s been tough to date in my 50s. I’m not starting in life. I have kids, a preferred way of doing things, and a set of friends. Unlike when I was last dating 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? Will he be equally interested in picking up one of my hobbies?

What about his and my kids? Are they supportive? Will they make room for this new person in my life or his life?

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

And on and on and on.

When does sex enter the picture?

And then the most thorny issue of all, sex.

I’ve been sexually active for over thirty years of my life. It feels hardwired into my makeup. I’m not the blushing nineteen-year-old virgin I once was. Avoiding sex while dating was easier in those days. It’s not now. It has become a way I express my love and affection.

I miss it. I want it.

So when? As a person of faith, I know I supposed to wait until I marry. But what if the guy I meet doesn’t want to marry again? What do I do then? Yell, Next! and start looking for someone new?

And does waiting to be sexual express who I am these days?

The importance of dating with self-integrity

My newest dating motto is to make decisions that align who am I. 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.

I’m finding this challenge to be about as hard as trying to ride a mechanical bull. I’ve been thrown and have hit the ground hard several times. But I’m determined to get back up, dust myself off, and try again.

I wish I had known all these preliminary issues I’d run into as I created my first dating profile five years ago. Maybe I could have spared myself a few tears and some embarrassing moments. But perhaps these bumps have been necessary.

Dating later in life certainly has taught me a few lessons. To be more patient with myself and to listen carefully to my readiness. To figure out what’s important to me by getting to know myself better.

Urging against a rush to judgment

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 are not. Until I entered this dating world, I had no idea it was so complicated.

But, like most things in life, I often don’t know what another person is going through until I face the same set of circumstances. This has taught me compassion and open-mindedness. I hope hearing about these dating experiences can help my friend be just as supportive of her single-again girlfriends.

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