Dating (Again) Over 50

Anne Lindyberg
7 min readNov 21, 2021
Photo by Mikhail Nilov from Pexels

I went on my first date in 3 years this past Friday.

Being on a dating site would seem to be a signal — to myself if not some portion of the world — that I am ready to date. Again.

What it’s actually doing is bringing up the realization that whatever it is that I have been doing in my romantic life for the prior 46 years, it hasn’t worked for me.

The man I met and had a date with, let’s call him “John,” (not his real name) is a wonderful person.

Not only that, he is quite handsome, smart and fit, almost exactly my age. If that weren’t enough, he is financially successful and appreciates the nuances of partnering that are at the core of eHarmony’s values.

He read my full profile before reaching out and shared his delight at little tidbits in it that he found interesting. He has allowed me to set the pace: from preferring a phone call over messaged exchanges, to wanting to meet in person before we’d communicated so much that we’d developed an attachment that we might later realize was based on projection.

A Prince Charming of the online dating world? For those who view these things thus, perhaps.

I don’t believe in Princes Charming though. Or perhaps I simply believe that partners forge themselves into royalty (fulfilling partnership) together, regardless of rank and birth. If you do find your true love, it’s a journey that will take you through your own, personal fire swamp, and probably theirs too. The Princess Bride taught me that.

We’ve had one lunch date. He picked up the check (which I appreciated), although when the server asked how to print the bill I would’ve been fine with splitting it. I didn’t feel that I’d pushed for the date — although I did want a meeting, I would’ve been fine with coffee — so I wasn’t going to offer to treat as I would’ve if I’d suggested the outing. I’ve learned men don’t typically like a woman who insists on paying early on, either, so there’s that. Such a quagmire, to navigate the opposing forces of convention and modern power dynamics. Expectations that sometimes contradict each other.

When he began dropping hints about another date, or even having me out to see his farm in the boonies (which does interest me, one of my parts is a solid country gal, but YIKES! Going to a strange man’s farm? Are other women buried there? Why am I thinking this, he’s been absolutely lovely?) I was flattered, interested and scared. A tough combination.

And my pretty-but-protective canine companion, Lila, seemed to think he was probably okay because she didn’t go directly into her Cujo-routine when he walked me out to my car. Not until he tapped on the window. And maybe he was nervous too, because tapping on the window of a touchy dog?

Afterward, I was coming back to myself, relaxing back into my own rhythms after an hour and 45 minutes, my leftovers next to me in a box (am I Holly Golightly because I just let a man buy me lunch and I’m going to get another meal out of it?). Actually in the hatch area because I didn’t want Lila eating them. I get Holly. Well really I just don’t like to waste food either.

Of course, we’re texting a bit now. And that’s fine. We’ve met, and I like him. I’m not sure I like-like him, but I do like him. I worry a bit, what if he like-likes me and I don’t like-like him… I sit with myself and my feelings, and I realize I’ve been in this energetic space before.

In the past I’ve had a part of me who has decided that a man I like, who like-likes me, that part of me has started “rallying the (internal) troops” shall we say. By that I mean, convincing other parts of me to start changing who they are in order to see if I can’t muster up some like-like, to give this nice man who is or may be like-liking me.

And then a new part showed up. She said “NO MORE.” She looks like cross between my Aunt Mary Louise, Janice Ian (who has coincidentally just released her first single in years, Resist, which I love) and me. New Part is an absolutely bad-ass crone with a flying mane of long, white hair and an attitude. And a guitar. A bit late for Halloween, but I never wear black anyway.

I wanted to text with John. But I didn’t want to engage in all the inanities that I’d gotten accustomed to my prior dating partners seeming to expect. I wanted to have fun. And I wanted to play. With him. On a metaphorical playground, which means that one or both of us might get skinned knees.

John had noticed and appreciated some particular things about me. Things that others had not only not appreciated, but tried to persuade me were wrong and needed to change. I valued that and it made me value him the more, and want to continue to get to know him.

Was this a green light to let my creative parts fly? It seems I thought so. And so I did.

On Saturday morning, less than 24 hours after our date, I had a joyous creative impulse. I said to him: wanna play a text game?

I’m not sure I even waited for him to reply before I started tapping out the rules.

The game is called “Unfit.” Here are the rules:

We play it in rounds. The first person (who becomes person 1 for the round) has to text the other (person 2) something true about themselves that could, in theory at least, make them unfit for an intimate partnership. The receiving person, after reading it, has to respond by one-upping. The catch is that what person 2 says about themselves — and it must also be something that would render a person, arguably, unfit for a relationship — does not have to be true. It might be true, but it might also be false. Person 1 has to guess whether the statement is true or false, as it pertains to that individual. Person 1 gets to ask a few follow up questions to aid in their decision and person 2 must answer. It’s a battle of wits.

If person 1 assesses the truth of person 2’s statement correctly, they win the round. If they are wrong, person 2 wins the round. Either way, person 2 becomes person 1 for the new round and you begin again.

If you can’t find something meaningful to talk about by playing this game, or quickly realize that compatibility is only skin (or hormones) deep, well, I don’t know what to tell you.

I didn’t anticipate how intense this would feel. I made up this game on the fly. Never even thought of it before.

At the moment, we’re in our second round. It’s Sunday, only 1 day later. That means I’m now person 2. I have just responded to his “this is what makes me unfit” revelation (which, although brief, could kick off an hours long conversation. If we ever talk or meet again we’ll certainly have some interesting personal truths to discuss) with my own. What I said was false, but plausible, according to the rules. It was also amusing, or might be considered by some I guess. I was amused anyway.

We’ll see if he is. He hasn’t responded yet. It’s given me time to write this 1500+ word reaction, or perhaps for him to block me on the dating app. Time will tell.

Throughout the text exchanges of round 1 and round 2, I have been feeling both terrified and exhilarated. In 15–20 texts, we’ve broached THREE topics that most couples getting to know each other would avoid, in the interest of establishing mutual attraction first.

Now if terror and exhilaration aren’t part of the deal in exploring mutual attraction, I don’t know what is. I’m particularly proud that my parts are forging a path for this exploration which does not specifically seek to terrify him, or judge him negatively. I would never want to do that. But I also appreciate the value in letting even a new, potential partner, see oneself fully so they have a clear idea of who they are getting involved with.

I’m also particularly unfond of having lovers yell at me for being who I am and telling me to change. Maybe my wild parts — fearless “show him!” parts — were born of those circumstances.

What I’m really interested in is establishing safety between us, and compatibility, as well as mutual attraction, if it even comes to that. I don’t WANT to be attracted to this attractive man if it’s going to turn out that we lack compatibility in our values or approach to life. I’ve found myself in this energetic place where attraction is possible but not yet present. And my parts — the parts who have probably always been interested in participating fully in my life — jumped in to make it fun and interesting.

No wonder men are afraid of post-menopausal women. We’re absolutely terrifying. I scare myself sometimes.

Now to see if he responds.

To be continued (maybe)….



Anne Lindyberg

Anne is a licensed counselor and consultant using Satir Transformational Systems in the midwestern US.