Dating After 50: Boundaries, Expectations, and the Trouble With Online Dating
I've been thinking about dating again, but every time I consider going back on those dating apps, I remember some of my previous experiences. And I'm not so sure I want to go through all that again.
I've met some interesting men online, and I've learned quite a bit about myself in the process.
One thing I've noticed is how much people can expect from each other before they've even met. And sometimes those expectations aren't even spoken.
Last year, I was talking to a man whose dating profile initially caught my attention. His pictures were very polished, showing him golfing and enjoying different activities. He appeared to have an interesting lifestyle, and I liked what I saw.
But as our conversations continued, I started getting a different impression of him.
Then one night, he sent me a live picture of himself.
I remember looking at it and thinking he didn't look nearly as good as he did in his dating profile. Looking back, I sometimes wonder whether those pictures had been heavily edited, possibly even with AI.
But what bothered me more was what he said afterward.
He told me that the natural thing to do was to reciprocate and send him a live picture of myself.
Now, wait a minute.
I never asked him to send me a picture. He chose to send one, and suddenly I was expected to return the favor?
That was one of many red flags for me.
It wasn't that I was unwilling to share a current picture of myself. It was the expectation that because he had given me something, I was somehow obligated to give him something in return.
I've spent enough years in relationships where I gave more than I should have, accommodated other people's wants, and sometimes allowed myself to become a doormat.
I've worked hard to change that, and I'm certainly not interested in going backward.
Then Came Someone Completely Different
This year, I matched with another man whose profile was actually pretty bland. Mostly pictures of his face, nothing particularly interesting.
But there was something about his main picture that I liked. He had this cute, boyish charm about him, so I matched with him.
Unfortunately, our first few messages weren't going anywhere. He wasn't very talkative, so I unmatched him.
Well, somehow he found me again.
This time, his greeting caught my attention, and I decided to give him another chance.
I started teasing him about his pictures because they all looked so different. Some appeared to be five or ten years old, maybe even older. One looked more recent.
It was like looking at five different versions of the same man.
His main picture looked like it could have been taken when he was around 40, although he was actually approaching 60.
I couldn't help teasing him about that, and somehow, we hit it off.
The more we talked, the more he opened up, and I discovered that he was much more interesting than his profile suggested.
Eventually, I learned that he was actually quite wealthy.
Having worked in wealth management in a previous career, I was familiar with that world. I've been around people with considerable wealth, so it wasn't something entirely new to me.
He started sending me live pictures of himself and his travels. I remember the first one was from an airplane, flying first class. Later came pictures from Spain, fine restaurants, and other places he visited.
He also sent several current pictures of his face. I enjoyed receiving them. It was interesting seeing the places he traveled to and getting little glimpses of his life.
The pictures also helped me make sense of those different versions of him on his profile.
He had obviously aged. His hair was gray now, and he looked like a man approaching 60 rather than the younger man in his main picture.
But I thought he was handsome. I actually thought he had aged quite well.
And while his lifestyle was impressive, it wasn't what made me interested in him. I enjoyed our conversations and the person I was getting to know.
Still, there was something I began noticing.
The Unspoken Expectation
I think I was actually the one who started sharing pictures.
I was shopping one day and saw a plant I liked, so I sent him a picture of it.
Sometimes I'd send pictures of my coffee, things I was doing out on the patio, or whatever happened to catch my attention.
That's just the kind of person I am. I take far more pictures of my surroundings than I do of myself.
But I never sent him a live picture of my face.
I remember going to get my hair done one day. I took a few selfies afterward, didn't like any of them, and ended up sending him the picture my hairstylist took of my hair.
My face wasn't even in it.
I'm just not someone who enjoys taking selfies. I'm not going to get all dolled up just to take a picture for a man I've never met. And I'm certainly not going to send one without makeup if I don't feel comfortable doing so.
As he continued sending pictures, I started sensing that he wanted one from me.
He never specifically asked, but I was picking up on it.
I've spent years learning to understand people through their behavior, their personalities, and what they communicate without necessarily saying it directly.
Much of that understanding comes from my own relationships and life experiences. I've learned to recognize patterns, and I trust my intuition.
In this case, I believed he wanted me to reciprocate.
So I decided to bring it up myself.
I told him I appreciated the pictures he had been sending, but I wasn't comfortable taking live pictures of myself.
Interestingly enough, he told me he wasn't comfortable taking them either.
I found that interesting.
Here we were, two people who apparently didn't enjoy taking live pictures, except one of us kept sending them.
And I hadn't asked him for any of them.
Was he hoping I would follow his example? That's certainly how I understood it.
But he never specifically asked me for one.
And that mattered to me.
Boundaries or Stubbornness?
Looking back, I can admit that perhaps I was being a little stubborn.
I liked this man. I found him attractive, enjoyed talking to him, and was interested in seeing where things might go.
So why wouldn't I just send him a picture?
It's a fair question.
But I've spent much of my life anticipating other people's needs and trying to accommodate them. Sometimes I gave people things they hadn't even asked for because I assumed that's what they wanted.
And I've paid a price for that over the years.
I've learned that just because I recognize what someone wants doesn't mean I'm responsible for providing it.
There's a difference between understanding someone's needs and taking responsibility for satisfying them.
That's why I wasn't willing to perform for a man simply because I believed he wanted something from me.
It wasn't about his money or whether I liked him enough.
And he could have sent me a hundred live pictures, but that still wouldn't have made me feel obligated to send one back.
However, I've also considered something else.
If he had simply asked me for a current picture, perhaps I would have handled things differently.
I might have sent one. I might have suggested a video call. Or I might have told him I'd rather meet in person.
I was never completely opposed to the idea.
I just wanted him to communicate what he wanted rather than leave me to respond to something that had never been directly asked of me.
At the same time, I recognize that being protective of my boundaries can sometimes make me less flexible than I need to be.
And that's something worth thinking about.
I don't want to become so guarded by my past experiences that I make it difficult for someone new to get close to me.
I want to be able to compromise because I choose to, not because I feel obligated.
And I think that's an important distinction.
What Happened to Simply Meeting Someone?
These experiences have also made me think about how differently people can present themselves on dating apps.
One man had a polished profile that initially attracted me, but the more I learned about him, the less interested I became.
The other had a rather boring profile with outdated pictures. I even unmatched him the first time.
Yet once we started talking again, I discovered someone much more interesting than I had expected.
It makes me wonder how many people we overlook because their profiles aren't particularly interesting. Or how many we become attracted to because of pictures and descriptions that don't really represent who they are.
I understand why people want current pictures. There are fake profiles, misleading photographs, and plenty of reasons to be cautious.
And to be fair, not every man I've talked to has expected live pictures.
But I think we've made getting acquainted much more complicated than it needs to be.
We're judging people through photographs, trying to understand them through text messages, and sometimes forming expectations before we've even sat down together.
With the second man, I would have been perfectly happy to meet him in person.
All he had to do was meet me.
We could have had coffee, enjoyed a conversation, and found out whether we actually liked each other.
No need to impress me with first-class flights or fancy restaurants. And no need for me to take fifty selfies to find one I felt comfortable sending.
Just two people getting to know each other.
That's what I miss about meeting someone naturally.
I want to see someone's expressions, hear his laughter, and find out how we get along in person.
I want to meet a man who knows how to communicate, who is comfortable with himself, and who understands that getting to know someone takes a little patience.
And while I've learned a great deal from my previous relationships, I'm still learning about myself, too.
Perhaps that's one of the things I find most interesting about dating at this age. After everything we've experienced, there are still things we discover about ourselves through the people we meet.
Hello… Are You Out There?
Which brings me to the picture that inspired this story.
It's an AI-generated image of me sitting at a café with a man who looks like someone I might actually be attracted to.
And I love the simplicity of it.
Two people enjoying each other's company. Maybe it's a crisp autumn afternoon, and we've just stopped for coffee after walking through the falling leaves.
Nothing particularly fancy.
Just a man and a woman who enjoy being together.
Of course, finding that person in real life is another story.
But I haven't given up on the possibility.
Hello… Are You Out There?
And I'm curious about the experiences of other women.
Have you ever felt pressured to reciprocate something a man gave you, even though you never asked for it?
Have you ever known someone wanted something from you but waited for him to ask instead of automatically giving in?
And how do you know when you're standing by your boundaries or perhaps being a little too stubborn?
These images are AI-generated, but the experiences and reflections are my own.
