Dating

Dating While Unemployed in Your 50s: What Happened to Me

Man in his fifties at a desk late at night during a stretch of unemployment.

Two Months From Homelessness, and Women Would Not Leave Me Alone

July 2024. Thirteen years at the same company and they called it restructuring.

I had a decent severance because of the tenure, so I did what a man does when he finally has some room to breathe. I made a plan. I was going to sit for the CSCS, and between that, my Health Master certification and my nutrition degree, I would be a strong candidate for just about any serious health and fitness job in the city.

So I put my head down and studied. Built the website in the gaps. Started writing what became The Midlife Comeback Plan.

And somewhere in there my Facebook algorithm lost its mind.

The DMs

Friend requests from women I had never met. New names in my inbox multiple times a week. This went on for months. I was not posting thirst traps; I was not sliding anywhere, and I was a middle-aged unemployed man reading about the phosphagen system home office.

I turned almost all of them down. And I told them the truth about why.

I am not fit for human consumption right now.

That was the actual sentence. I used it more than once, and I meant every word of it. I had no job, no income coming in that I could count on, and no business offering anybody a version of me I would not have wanted to date myself.

Here is the part that still makes me laugh. Some of them circled back months later. “Are you fit for consumption yet?”

Then the Floor Went Out: Dating While Unemployed and Broke

I failed the application portion of the CSCS twice. First time by three questions. Second time by one.

One question.

Around the same stretch, my unemployment ran out, and the part-time nutrition job I had going on the side went under. And let me tell you something about money you have saved. If nothing is coming in behind it, that money goes FAST. Faster than you think, faster than the spreadsheet you made says it will.

Being unemployed in your fifties hits different than being unemployed in your thirties. In my thirties I knew something would turn up. My parents were still alive, and in the worst-case scenario, I could go home for a while. In my fifties, age discrimination is real; whether anybody will say it out loud or not, my parents are gone, and the math had me a couple of months from being homeless.

That is not a figure of speech. I sat down and counted the months.

It was at this point I decided I will never let anyone have sole power over how I make money.

What the second failure actually did

After that second exam I had a come to Jesus meeting with myself.

I had been chasing the CSCS so I could work with athletes and fitness enthusiasts because I thought that was where the money was. And sitting there one question short for the second time, it finally landed that I had been building toward the wrong customer. I did not want to program jumps for a nineteen-year-old with a vertical. I wanted to serve men like me. Forty, fifty, coming out of a marriage or a layoff or a diagnosis, trying to figure out what the second half looks like.

That failure is the reason this website exists. I wrote about it in The Comeback Code because it was one of the few times in my life a closed door was that obvious about it.

So there I am. Broke, unemployed, and more clear on my purpose than I had been in twenty years.

And the women kept coming. Facebook, real life, people I actually know telling me they had a friend who was interested.

Why That Happens to Men Over 50

It was never the unemployment. I want to be careful here because I have caught myself telling this story like being jobless is some kind of cheat code, and it is not.

What was actually true is that I was completely absorbed. Studying, building, writing, and hunting work. I woke up with somewhere to be in my own head. There was no room in my week for a campaign, and a man with no campaign running is a very different animal than a man performing not having one.

That absorption is legible. It shows up in how fast you answer, whether you rearrange your Tuesday for a maybe, whether you are the one telling the story or the one waiting to be included in it. Attention is the one thing a man cannot fake having plenty of, and where he spends his is completely visible.

Our ancestors did not have Facebook, but they had this exact thing. The man who was good at something the group needed never had to advertise. The man with nothing going on had to.

Now the part I got wrong

I went on a few dates during that stretch anyway.

Two months from being homeless, in my fifties, with a countdown running in the back of my skull, and I went out with people. I knew better. I have known better for years. Never start dating a woman while you are in a vulnerable place.

So why did I do it? Because I had run this play before. I was unemployed in my thirties, and it went great. I figured I had the formula, and I could get away with it again, and I told myself dating would take my mind off my problems.

It amplified them.

I was honest with those women about my situation, same as I had always been. Honesty was not the issue. My energy was different and they could feel it, and no amount of disclosure fixes an energy problem. The interest got me in the door. The state I was in decided what happened after.

Absorption is what makes women interested. The place you are standing in decides whether you should do anything about it. Two different things, and men mix them up constantly.

Never think you are above the game

This is the rule I want you to take out of here.

After you have had some success with women, you start cutting corners. You get a little arrogant. You figure you can steer around a thing you would have respected five years ago because you have steered around it before.

Dating is a vibe thing far more than it is a technique thing. Women scan for it. The ick is real, and they pick it up like a drug dog picking up weed at a Snoop Dogg concert. You do not talk your way past that. There is no line, no opener, no framework that covers for a man whose insides are in a state he has not dealt with.

Which means the whole game runs on self-awareness. Not tactics. Knowing where you actually are on a given Tuesday and being willing to say out loud that today is not the day.

I am not fit for human consumption right now is not a rejection line. It is a status report. And the men who can give one honestly are the same men who do well when the status changes.

Where it landed

July 2025. Twelve months to the day, roughly, I got a job. Back in IT, which is what pays the bills, while I build the coaching business that came out of failing an exam by one question.

I am fit for human consumption these days. It took a year of baking, cooking, and a hard look at what I was actually for.

If you are in the middle of your own version of that stretch, the advice is not to fake calm and go get some. It is to go be absorbed in the thing that needs you, take care of the people in your corner, and be honest enough with yourself to know when you have no business bringing another person into it.

The interest will show up. It always does. Just make sure there is somebody home when it knocks.

The whole system is in The Comeback Code, including the chapter about failing that exam and what it redirected me toward. Body, mind, purpose, money, relationships, and brotherhood, in that order and on purpose. Dating is chapter seven, and it works because of the six chapters sitting in front of it.

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