Chapter 1. Gary Harbor Chophouse

12 min readDec 15, 2023

I’ll start with the latest. To get some truths out of the way on what it’s like to take part in online dating for the first time. At age 56. After 11 years of being completely and datelessly single.

And 20 years of marriage before that.

My plan is to talk about the process here. Each one of my Trysters, as I refer to the men I experience on dating apps, has a story as it relates to my journey. My goal is that in learning about my current path, you’ll think about your own journey.

Whether you are on one, or just considering the idea of going on one. Of any kind.

I won’t list the Trysters in the order they happened. The plan is to jump around. I’ll write about each one as they fit within what I’m learning about myself. Plus, some of them overlap.

Sometimes within the same day.

No judgment. I’m a liberated, fully actualized, 56-year-old. A very young 56, mind you. But, as people say, I’m a Grown Ass Woman. And I’m fully embracing my power. You don’t have to worry about keeping it straight. The journey, and the lessons, will be clear. Plus, I have faith in you, Dear Reader.

And in your dirty little mind.

Any details on locations as small as cafes or as big as states or regions, will not be given. All fake locales, titles, and descriptions.

But the stories are true.

Also, the men’s names and details have been changed to protect the ridiculous. Their fake names are based on where we make plans to go on our first date.

Hence, the latest Tryster, Gary Harbor Chophouse.

Gary and I matched on one of the three dating apps I currently use: Tinder, Bumble, and Hinge. I liked his pictures. They were taken in spots I recognized from all over our state.

Plus, unusually, he smiled in most of them. A picture of a smiling 50-something man can be disastrous. But his smiles were nice. Natural. Not at all creepy. Plus, he’s my age. And he’s taller than me, which, in the most outdated way, is a necessary expectation.

Basically, I thought Gary was cute.

His profile also said that he’s newly in an ENM relationship. ENM stands for Ethical Non Monogamy. This is when a committed couple decides to stay together in their relationship, while also dating other people on the side. That’s the ‘Non Monogamous’ part.

It’s ‘Ethical’ because both partners know about it. And mutually agree to it. This also applies to any new partners or possible partners. Being honest and upfront is the fundamental way to make it work.

Otherwise, it’s just an affair.

They’re often rooted in a sexless, but not necessarily a loveless, marriage or committed partnership. But that’s not always the motivation. People may be interested in exploring their sexuality. Their kinks. It can be because one person can’t have sex. It’s often utilized as a way to stay together for financial reasons or insurance benefits. Or so that partners can stay under the same roof to co-parent the kids.

It’s a fairly new way to contextualize a long term relationship. Something beyond just married or divorced, or partnered and split up.

Sometimes it’s because one person in the couple is unwell. And that is the case with Gary’s wife. She is sick and has been for a long time. It’s horrible. When we matched on the app he explained his situation right away.

I accepted it. I didn’t tell him why. I’ll just say for now that I was okay with it.

We had a good chat flowing on the app, so he asked if we could text offsite. When you first send your number to someone on a dating site, a glaring red popup garishly warns you that you’re about to do something bonkers and unsafe.

But again, I was cool with it.

From that point forward, every day for three full weeks (so far, a lifetime for most Trysters), all we did was text. So many texts per day. He was really good about checking in. I never had to text him first on any given day.

In the beginning, there was a lot of talk about the weather. A ridiculous amount about how cold it was outside. But eventually, there was talk about families, jobs, school. The mundane, but important, conversation subjects.

I call it Dating Due Diligence. I started to draw him out. I know what I’m doing.

That’s when the texts started getting flirty. For example, if I texted I was cold, he would say, ‘Should I come over and warm you up?’ It seemed right because I thought we were at the point when we needed to move in some sort of direction.

And, really, Trysters are just so easy to influence in that way. I’m not looking for a buddy. Or a weatherperson. I want to see if there’s a real connection. Then I can determine what I want to do, or not do, with it.

In time, Gary started sending messages that moved from flirty to sexual. Especially if he’d had a cocktail. The first time he did so, it was out of the blue, and without context. The message said, ‘I think foreplay is essential. My favorite thing is giving oral. It’s what gets me going.’

It didn’t exactly match the tenor of his other messages. I found it a little odd and out of place. All I could think to say back was, ‘I see you Gary, shooting your shot’, and he replied that he had no idea what that meant.

Oh boy.

Still embracing his newfound assertiveness, Gary made plans with me to meet at the Harbor Chophouse on the following Tuesday. But a few days later, he started stalling. Moving the date around. Postponing. Telling me his Dad was sick. All while this new way of texting continued. Very soon, I wasn’t having it. I started to think he was all talk.

So I called him out. As I do.

I suggested that maybe he was just interested in using our texting as a way to get off. I told him that my existence in his world for the sole purpose of jerking off wasn’t something I was interested in continuing to do. Suddenly, he suggested that we go get burgers and beer. At a pub. No fancy chophouse. That seemed like a better fit for him. It was definitely a better fit for me. A date was even set.

And he didn’t mess around with it this time.

On the night of the date, I met him at the pub. He was waiting outside. Yeah, I thought, he might be redeeming himself. He was definitely cute. I walked towards him, feeling my inner Yasmin as I went.

Yasmin is a woman from TV who perfectly represents and displays the confidence, self-worth, and badassery I’m newly emanating and feeling about myself. Her example, as well as many other fantastic women, helps me learn and relearn the things that influenced me while going from a teenage girl to a woman in my 20s during the 1980s.

As well as the things I had to unlearn because of my 20-year marriage.

I gather her fierceness when I want to lift myself up while chilling myself out. It works every time. She even makes me walk better.

Gary and I hugged. We got a table and some beer. We ordered food. He was very flirty. Complimentary. Touchy-feely, even. I could almost sense the moments right before he decided it was time to reach over and put his hand on my arm.

After having a few, he told me more about his family. He and his wife decided to get divorced awhile ago. But her illness became so unstable and the outcome so unknown, they recently decided to stay under the same roof. They lived in separate bedrooms, as married friends, in order to look out for each other and to give their 14 and 16-year-old daughters as much time with them together as possible.

His wife had an ENM relationship on the side, too.

Then he talked about how all of them; the girls, his wife, and her lover, helped him get ready for our date that night. They made sure his hair was right. They picked out what he was wearing. They even gave him advice on what to say. What to do.

And evidently, they knew a bunch of stuff about me. They were all on hand that night to see him off.

Uh-oh.

Suddenly, there was a lot of pressure on the date. I immediately felt the weight of it, just as I felt the weight of his hand each time it touched my arm.

He kept going. I tried to bring up other subjects, but he was determined to describe his entire relationship with his wife, from when they first met, through every step along the way, up until the present time.

Then he paused and said, “And then I met you.”

Oh shit.

Calm yourself, Annie — maybe you’re panic-spiraling for no reason. This is the lie I told myself as he smiled and looked across the table. And touched my arm again. I was in trouble. I didn’t even know if I really liked this guy or not. Plus, I didn’t fully understand his goals or motivations for dating.

We’d been in each other’s presence for barely an hour.

And maybe it was because of that slap of seriousness, or because I was looking for a way out, but the other red flags present during the date were suddenly spinning and swirling around me, flapping at my shoulders.

Think Annie.

First of all, towards the beginning of the date, he said that “God created us.” I was already feeling the beer by then, so I pointedly responded with, “I think God is just love and science.”

He ignored me.

Gary also mentioned that they home-school their daughters. And how much he disliked the movie, ‘Barbie’. He commented on the small town where he and his wife grew up, too. In another part of the state, away from the cities. He thought people are just, “too angry these days”. Also he graduated from the state university that’s out in the boonies. The one with all the hunters and cowboys.

Jesus Annie.

The reality finally hit me in the head: Gary Harbor Chophouse is a Republican. The polar opposite of me.

I was finally and acutely aware of the fact that in all those days of texting, we never really discussed anything more than the weather, small talk, and sex. The realization washed over me. And it moved all around in my not quite sober brain. I no longer could keep my thoughts in my head, and I blurted, “So, who did you vote for in 2016?”

Deep down, I already knew he what he was going to say.

But then, with a brash lack of shame, self-reflection, and credibility, he said that in 2016 he didn’t like either candidate, so he wrote someone in. Each of us instantly recognized it as a terrible attempt at lying. Gary is not only a Republican, he’s a Trump Republican.

Infinitely and seismically worse.

My kids are Black. They identify that way because of the pride they have in themselves and their culture. And because, as they say, in America, in all the positive and mostly negative ways, they are seen as Black.

And white Gary Harbor Chophouse knew this.

So I asked, failing to not sound irritated, “Regardless of your politics, you couldn’t have just held your nose and voted for the one who isn’t a virulent racist?” And his answer stopped me cold. The spinning and swirling were gone.

“You only ask me that because of your children.”

Gary Harbor Chophouse thinks only white people with Black relatives should question or care about whether politicians are hateful racists. He didn’t even take two moments to consider what he was saying.

Or, that it was, in fact, racist.

In that moment, I slowly put down my beer and my napkin, and I started to put on my jacket. He got it. Even though he was still sort of trying to be Date Guy, he knew I was DONE.

It was awkward and very obvious that I was no longer cool with any of it.

When we got outside, we realized we were walking in the same direction. And when we got to to my turnoff, another absurdly maddening thing happened.

I went in for the half-hug. Just a parting, yet not friendly, yes-that-sucked-but-it’s-done-so-let’s-embrace-to-have-it-officially-be-over, kind of a hug. The shrugging, “welp” hug. During that attempt, and before I knew what was happening, he pulled me back and was kissing me.

Really kissing me.

I’m not going to lie, it shocked me so much that I went into stunned auto-pilot and started kissing him back. And for about three and a third seconds I thought, Gary Harbor Chophouse is a good kisser.

But the reality was still there. I quickly stopped and stepped away. And when I looked at him he was so disgustingly pleased with himself.

And it finally made sense.

This date wasn’t about me. He had no interest in knowing who I am as a person. And he certainly did not consider, or seemingly even care, about our now-obvious, vast differences.

And that kiss wasn’t about me, either.

It was about Gary going home and having a story to tell the people waiting for him there. A little conquest to report. I have no doubt he decided, beforehand, that he was going to kiss me, like that, whether we had a good date or not. I could even picture his teenagers, his wife, and her lover telling him to make sure and get a kiss at the end of the night.

So Gary Harbor Chophouse got his first big, completed Ethical Non Monogamous date out of the way. And he used me to do it.

I was pissed. That seething, quiet kind of pissed.

I felt used. Gross. And stupid. And so fucking pissed.

After that night, the texting stopped. When the radio silence lasted exactly three days, I had a terrifying thought. Don’t some people think they should wait and not text or call someone until three days after a date? Oh God, is that what he was doing?

And it just made me more angry.

So I texted him first, for the first time: ‘Hey. It’s been a few days so I’m touching base. I don’t think we agreed on some important things during our date. Specifically about religion and politics. And that kiss. I prefer to be honest and upfront about it. I don’t like loose ends. Good luck on your search and my best to your wife and family.’

When he sent his wobbly, ‘Oh yeah, I was thinking the same’ response, I immediately wondered, then why didn’t you take the time to text me and tell me that? After everything, Gary Harbor Chophouse waited for me to be the one to say it. To officially cut it off.

Because he had already gotten what he wanted out of it.

It was weak. Pathetic. Subversive.

Mostly I’m mad at myself. I didn’t do true Dating Due Diligence. I didn’t ask the right questions or say anything real to help me determine if we were a good match or not. I should have just asked him if he was registered to vote. Anything that could’ve started an important conversation.

I didn’t even take the time to notice how much his profile photos looked like the one in that famous photo array of Trump Dudes who ‘like to be outside’.

So Gary was a terrible bust. And not a great person. But it was also on me that I didn’t center what was important to me before I agreed to meet him. Everything I described should have tipped me off. It was all a glaring red popup message, telling me I was doing something bonkers and unsafe.

My lesson is recognized. And learned.

My hope is that you have learned something, too, Dear Reader. Because if I can’t teach myself, and you, as we go, what is Tryst 56 even for? My experiences are your blueprints. Or your warning signs.

And there are so many more Trysters to talk about.

Let’s go through it together.

XOXO, Annie

My song for Gary Harbor Chophouse:

Go home Gary.

Ethical Non Monogamy