Dating at Damn Near 50

Let me introduce myself before we get into this bullshit.

I'm Dakota Denise. I'm a freelance writer, a business owner, and a woman knocking on 50's door who somehow decided it would be a good idea to start dating again.

So naturally, I'm writing about it.

Welcome to Dating at Damn Near 50: The Dating Chronicles, where every date that goes wrong, every red flag that starts waving, every man who circles the block when the whole damn neighborhood has already burned down, and every grown-ass male who makes me stare at my phone and say, “Now why the fuck would you say that?” has the potential to become a story.

Names will be changed.

Nicknames will be earned.

Feelings may be hurt.

But the stories? Oh, the stories will be told.

Because according to some men, women are complicated.

We're emotional. We change. We switch up. We don't know what we want.

I disagree.

Most women aren't nearly as complicated as we're made out to be.

The problem is that some men don't introduce themselves.

They send a representative.

The representative is attentive. The representative communicates. The representative asks questions. The representative makes plans. The representative is consistent. The representative tells you he's intentional and looking for something meaningful.

Baby, that representative is EMPLOYEE OF THE FUCKING MONTH.

But eventually that poor bastard gets tired.

He's been working overtime.

No lunch breaks.

No PTO.

No benefits.

And eventually, the representative clocks the fuck out.

And that's when the real motherfucker finally reports for duty.

Suddenly communication changes.

Effort disappears.

Plans get weird.

Texts go unanswered.

The consistency you met somehow develops a severe allergic reaction to being consistent.

Then the man has the nerve to ask:

“Why did you change?”

I changed?!

Sir, I am responding to a staffing change.

The employee who interviewed for this position apparently no longer works here.

THAT is what these stories are about.

Not male-bashing. Not pretending women never fuck up. Not looking for perfection.

I'm documenting what dating actually looks like from my side of the table as a grown woman who knows what she wants, has her own life, her own businesses, her own ambitions—and absolutely no desire to raise a grown man into somebody's husband.

And gentlemen from my past, please hear me especially clearly:

If you're thinking about spinning the block, make sure there's still a block to spin.

Because some of y'all keep circling addresses that don't exist anymore.

Baby, the house is gone.

The street has been renamed.

Google Maps said ROUTE UNAVAILABLE.

Whatever woman lived there 10 or 15 years ago has MOVED.

So if you come back, you're meeting me again.

And if you show up with the same bullshit wearing a different shirt?

Congratulations.

You're probably getting a nickname.

Because I'm a writer.

And if this date doesn't work out...

at least the story will.

Part 1: Mr. No Sequence

Dating at almost 50 is starting to feel less like looking for companionship and more like conducting unpaid psychological research.

At this point, I don’t even know if I’m dating anymore.

I think I’m collecting data.

Every time I open Facebook Dating, I feel like I should have a clipboard.

Subject #47: Male, 38. Attractive. Appears normal in photographs. Further observation required.

That’s basically how I met Mr. No Sequence.

I was minding my business, scrolling through Facebook Dating, when I saw that somebody had swiped right on me.

Okay.

Let me investigate.

I clicked on his profile.

Thirty-eight.

Cute.

Nice smile.

Looked like he had some sense.

And before anybody says anything about the ten-year age difference, I’m 47, about to be 48. I’m grown. He’s grown. Nobody needs a permission slip.

So I swiped back.

Match.

Here we go.

The conversation started the same way most dating-app conversations start.

“Hey.”

“Hey, how are you?”

“I’m good. How are you?”

You know. The usual two strangers politely confirming that neither one of us has died since creating our profile.

But surprisingly, the conversation actually got better.

We started talking about what we did for a living, what we were interested in, what we were building.

Now THAT will get my attention.

I’m a freelance writer. I own a 420-friendly clothing line, and I have a production company connected to my writing because eventually I want to take some of these stories out of my head and off the page and put them on a screen.

When I told him that, he seemed genuinely interested.

He started telling me about cameras and equipment he had. We talked about filming. Production. Different ways I might be able to bring some of my work to life.

Okayyyyy.

Now we’re talking.

Because you can be fine all day long, but if I can actually have a conversation with you?

If we can talk about something besides sex?

If you have ideas?

If I mention a goal and you can contribute something intelligent to the conversation?

Now you have my attention.

By the end of that first conversation, I was thinking, Okay. This might actually be somebody worth getting to know.

Notice what I said.

GET. TO. KNOW.

Apparently, Mr. No Sequence heard something completely different.

Because the next day, I get a text.

Good morning.

Good morning.

Everything normal.

Birds chirping.

Sun shining.

Civilization still intact.

And then this motherfucker sends me a message basically asking me to come over and see whether I could grip it with one hand or whether I would need two.

Sir.

Excuse me?

Did I miss a meeting?

Because yesterday we were discussing cameras.

TODAY I'M BEING ASSIGNED A GRIP TEST?

How did we get here?

There was no transition.

No flirtation.

No buildup.

No kiss.

No date.

No dinner.

No “you looked beautiful today.”

No “I enjoyed talking to you.”

Hell, you didn't even give me enough time to become delusional and start imagining us on vacation.

We went from:

“I have cameras. I might be able to help you with your production work.”

to:

HOW MANY HANDS YOU THINK IT'LL TAKE?

SIR.

THERE ARE STEPS TO THIS SHIT.

So I asked him what he was talking about.

Because sometimes I like to give people the opportunity to hear themselves explain their own foolishness.

He immediately backed up.

“Never mind.”

Oh, no.

No, no, no.

We’re not “never minding” now.

You opened the door.

Come on through it.

I called him.

Because at 47 years old, I don't have time to spend six hours decoding text messages.

We started talking, and I explained something that I genuinely thought grown people understood.

There is a sequence.

You meet somebody.

You talk.

You get to know each other.

You flirt.

You establish whether there’s chemistry.

Maybe you go on a date.

Maybe another date.

Things naturally progress.

Eventually, depending on what both people want, we might arrive at the portion of the program where we start discussing what requires one hand, two hands, both feet and a prayer.

But we were not there.

We weren't even in the parking lot of there.

This man listened to my entire explanation and said:

“I don't do sequences.”

...

Oh.

Okay.

Well, that explains everything.

Ladies and gentlemen, allow me to formally introduce:

MR. NO SEQUENCE.

This man does not believe in chronological order.

Beginning, middle and end?

Government propaganda.

Step one before step seven?

Absolutely not.

Mr. No Sequence wakes up, puts his shoes on, and THEN looks for his pants.

He probably puts the cereal in the refrigerator and the milk in the cabinet.

He probably walks into a restaurant and asks for the check before he orders.

Because apparently sequence is beneath him.

Fine.

Now, you would think the Hand Olympics would be enough excitement for one dating interaction.

You would be wrong.

Somehow, during another conversation, we started talking about Apple products and technology.

I mentioned my 22-year-old son helping me set something up because my children have officially reached the age where they look at me struggling with technology the same way I used to look at older people trying to program a VCR.

That's when Mr. No Sequence casually mentioned his kids.

Kids?

Plural?

I paused.

“You have kids?”

“Yeah.”

Interesting.

Because unless my eyesight had suddenly joined the witness protection program, I could have sworn his Facebook Dating profile said he didn't have children.

But okay.

Maybe I remembered incorrectly.

Maybe he hadn't updated it.

Maybe there was an explanation.

So I asked the most basic question one human being can ask another human being after discovering that human being has children:

“How many kids do you have?”

This man responded:

“Why does that matter? I don't plan on introducing you to my kids.”

Sir.

WHO ASKED TO MEET THEM?

I asked HOW MANY.

I did not ask for their names.

I did not ask what school they attend.

I did not ask their clothing sizes.

I did not ask what they wanted for Christmas.

I did not ask whether they preferred pancakes or waffles on Saturday mornings.

I did not ask what time I needed to pick them up from soccer practice.

I DID NOT SUBMIT AN APPLICATION FOR STEPMOTHER.

You volunteered the information that you have children.

Your dating profile said you didn't have children.

Naturally, my brain—because it enjoys sequences—went:

Profile says no kids → Man says kids → Ask how many kids.

That's it.

That's the entire investigation.

Nobody was trying to infiltrate the family.

But Mr. No Sequence was already protecting these hypothetical introductions like I had shown up at his house carrying juice boxes and yelling, “WHERE MY STEPCHILDREN AT?”

Sir, I don't know those babies.

I don't WANT to know those babies yet.

At this point, I'm still trying to get to know YOU.

And frankly, the investigation isn't going particularly well.

Because within an extremely short period of time, I had learned three very important things.

His dating profile and his actual life apparently weren't completely acquainted.

He considered a normal question about his children suspicious.

And most importantly:

This man does not do sequences.

Which, ironically, was the most truthful thing he told me.

Because there was absolutely no sequence to any of this shit.

Business conversation.

Good morning.

Penis.

Never mind.

Apple products.

Surprise children.

Interrogation.

That wasn't dating.

That was six unrelated television episodes playing on shuffle.

And this is what I keep trying to explain about dating when you're a grown-ass woman.

I'm not offended that a man is attracted to me.

Please.

I'm damn near 50, not dead.

Sex exists.

Flirting exists.

Chemistry exists.

I like all three.

But I need you to understand something:

There is a fucking sequence.

You cannot meet me on Monday discussing my production company and wake up Tuesday trying to turn my hand into a measuring device.

At least let me finish my coffee.

At least find out my middle name.

Hell, find out whether I'm allergic to shellfish.

Give the plot time to develop.

Because maybe that's the real problem with modern dating.

Everybody wants to skip to their favorite chapter without reading the damn book.

They want intimacy without familiarity.

Access without effort.

Sexual chemistry before establishing whether you can hold a regular conversation for three consecutive days.

And when somebody says, “Wait a minute. Can we actually get to know each other first?” suddenly we're asking for too much.

No, baby.

I'm asking for Chapter Two to come after Chapter One.

That's not high maintenance.

That's literacy.

So Mr. No Sequence and I were clearly not going to work.

But I will give that man credit for one thing.

He gave me a story.

And considering I'm a freelance writer, that's probably the most productive thing that came out of the entire situation.

He had cameras.

I had stories.

And somehow, less than 24 hours later, he had me questioning the structural integrity of the modern dating process.

Maybe we did collaborate after all.

Just not the way he thought we would.

And wherever Mr. No Sequence is today, I hope he's doing well.

I hope he's happy.

I hope his children are thriving.

And I sincerely hope that one day he meets a woman who doesn't do sequences either.

They can have a beautiful life together.

They'll have sex before learning each other's last names.

Get married before the first date.

Have the honeymoon six months before the wedding.

And somewhere in between, maybe—

just maybe—

she'll finally ask him how many fucking kids he has.

Part 2: Mr. New Leaf 🌿

There are two kinds of Men you meet while dating.

There are new men who come into your life with absolutely no history, so you have to give them enough time to reveal who they are.

And then there are men from your past.

Those motherfuckers come with files.

Documentation.

Previous incidents.

Archived footage.

Witness statements.

Exhibits A through Z.

So when a man from your past comes back talking about how much he's changed, he isn't starting with a clean slate.

Sir, we have records.

And this particular man?

I've known him for somewhere between 10 and 15 years.

We've never really been in a traditional relationship. We've dealt with each other off and on over the years. There was a time when he wanted more from me than I wanted from him, and eventually life did what life does.

We'd reconnect.

Disappear.

Reconnect.

Disappear.

Nothing particularly unusual.

Except there was one thing about him that had always bothered me.

Consistency.

Or more accurately, his complete inability to locate any.

For example, years ago, I planned an entire weekend for us.

Not dinner.

Not “Let's grab a drink.”

A WEEKEND.

I got us a suite at a casino. Made plans for dinner at the steakhouse. Had gambling money. The whole grown-folks getaway package.

And this man knew about it.

Then Friday came.

And he disappeared.

Sir?

Hello?

You know we have PLANS, right?

Nothing.

So eventually I said fuck it.

I started posting on Facebook about taking myself on my own damn date because clearly the person who was supposed to accompany me had been abducted.

Wouldn't you know it?

Lazarus rose.

Suddenly my phone worked.

He apologized. Gave me whatever explanation he gave me at the time, and against my better judgment, I went and got him.

And we actually went.

Casino.

Suite.

Dinner.

Gambling.

The whole thing.

I paid for everything.

The next morning, we stopped at QuikTrip.

I realized I'd left my purse back at the hotel.

“Damn. I wanted something out of here, but I left my purse.”

Now, ladies, gentlemen and members of the jury, please understand:

I had just paid for the hotel.

Dinner.

Entertainment.

The entire weekend.

This man looked at me and essentially said:

“Well, I guess you ain't getting nothing then.”

...

I'm sorry.

WHAT?

This wasn't Tiffany.

It wasn't Gucci.

It wasn't even Target.

WE WERE AT QUIKTRIP.

I wasn't asking for a handbag.

I probably wanted a fucking drink and some chips.

This man got out of MY car, walked into QuikTrip, purchased whatever HE wanted, came back outside, got back into MY car and continued with his morning.

And somehow, ladies and gentlemen, I did not leave him at that QuikTrip.

Growth.

Because present-day me?

You'd still be standing next to Pump 7.

Later, when I brought it up, he tried to clean it up.

“Well, you could've come inside. I would've bought you something.”

Would you?

Because that's fascinating.

Because the man sitting in the car five minutes earlier seemed extremely confident that I wasn't getting shit.

Apparently there was an invisible second half to the conversation that only he could hear.

But that was him.

Inconsistent.

And inconsistency eventually became the theme.

Years later, his brother passed away.

I was there for him.

Because regardless of whatever our relationship was, I cared about him.

Then my sister died.

And I needed somebody.

I needed a friend.

I needed comfort.

I needed somebody familiar to just be there.

He came over.

Things happened between us that weren't even supposed to happen, because sex wasn't what I needed.

I was grieving.

I was hurting.

And shortly afterward, he got a message from somebody about wherever he was supposed to be.

And this man LEFT.

I was crying.

Mourning my sister.

Emotional as hell.

And he walked out.

And here's the part that still makes me want to go back in time and shake myself.

I chased after him.

Yes.

Me.

A grown-ass woman.

Running behind a man who was actively demonstrating that being there for me wasn't important enough for him to stay.

And this motherfucker was so determined to leave that he damn near ran over my foot getting away.

That's when something in me finally clicked.

What the fuck am I doing?

I had been there when he experienced loss.

When I experienced mine, this was what I got?

No.

That chapter needed to close.

And for the most part, it did.

Over the years there might be a text here.

A Facebook interaction there.

Nothing substantial.

Until recently.

Because apparently Facebook Dating is where unfinished business goes to apply for a sequel nobody ordered.

I'm scrolling through my likes one day when I see a familiar face.

THIS motherfucker.

He swiped right on me.

Sir.

You know me.

You have my phone number.

You've had access to me for over a decade.

Why the fuck are you swiping right on me like we're strangers at a singles mixer?

So naturally, I swiped right back.

Not because swiping right meant he automatically had access to me again.

Absolutely not.

I needed answers.

I messaged him through Facebook Dating.

“Why are you on my Facebook Dating profile when you have my number?”

Then I texted his actual phone.

Because now I'm conducting a multi-platform investigation.

His answer was basically:

“I saw it and liked it.”

Okay.

Cute.

But understand something.

Knowing me previously does not give you permanent access to me.

You don't get grandfathered into my life.

This isn't an old cell-phone plan.

So I explained exactly what I was looking for.

If you're trying to come back into my life, you need to SHOW UP.

Not because we have history.

Not because we've slept together.

Not because you knew me ten years ago.

You need to show genuine interest in the woman I am NOW.

He acknowledged that.

He even started talking about our history.

He told me he appreciated how I'd been there for him when he'd lost people close to him.

And I reminded him:

“You weren't there for me.”

To his credit, he admitted it.

He apologized.

Then he told me he'd seen that I was dating again and figured he'd try to “ease his way back in.”

Ease your way back in?

Sir.

This is not a swimming pool.

But okay.

Continue.

Then came the speech.

You know THE SPEECH.

The speech men give when they've supposedly reached a new stage in life.

He's older now.

Wiser.

He's looking for something serious.

He wants to date.

He wants courtship.

His intention is marriage.

Wonderful.

Beautiful.

Hallmark is crying.

Except I noticed something.

He told me what he wanted.

He never actually said he wanted those things with me.

There's a difference between:

“I'm looking for marriage.”

and:

“I want to explore building something serious with you.”

So I heard him.

But I didn't start picking wedding colors.

Tuesday came.

We talked on the phone for almost two hours.

And it was actually nice.

We caught up.

We talked about life.

There was history there, so conversation came naturally.

For a moment I thought:

Okay.

Maybe he really has changed.

Maybe we're older.

Maybe we're wiser.

Maybe Mr. QuikTrip has finally learned that when a woman spends hundreds of dollars taking your ass on a casino weekend, YOU CAN BUY HER A FUCKING GATORADE.

Maybe this is different.

Then Wednesday arrived.

And apparently the new version of this man had a 24-hour free trial.

Because that motherfucker disappeared.

Not literally.

His thumbs still worked.

Barely.

But communication?

GONE.

I would text him.

Hours.

Eventually I'd get something back.

Then more silence.

This man works overnight, so I was trying to be reasonable about his schedule.

Then I found out he was OFF.

Oh.

OH.

So your phone didn't fall into the Mississippi River?

The FBI didn't confiscate it?

Apple didn't remotely disable texting?

You were just...

off?

The last time I heard from him Wednesday night was around nine.

Then nothing.

Until Thursday morning.

“Good morning.”

GOOD MORNING?!

No, sir.

We were just on the phone for TWO HOURS Tuesday talking about intentions, courtship, marriage, maturity and all the wonderful improvements included in the 2026 software update.

Wednesday came and your ass reverted to factory settings.

And this is where people love saying:

“It's only been a day.”

Exactly.

It only took ONE DAY.

That's my point.

If you're trying to convince someone you've changed, the beginning is when you should be the MOST intentional.

You don't get to reenter somebody's life with a PowerPoint presentation titled THE NEW ME, then immediately demonstrate the same behavior that got the old you removed.

Then Thursday came.

I needed help with a writing project.

Perfect opportunity, right?

I'm a freelance writer, and I was working on something where I needed perspective from a man 50 or older about how his body has changed with age.

Nothing complicated.

So I texted him.

Basically:

“Yo, you're 50. I need a man's perspective for this project. How is your body treating you?”

Simple.

Especially considering this man had JUST spent two hours talking to me Tuesday.

No response.

An hour.

Nothing.

Two hours.

Nothing.

Three hours.

And that's when the little voice in my head said:

There it is.

Not because somebody has to respond to every text within 30 seconds.

People work.

People sleep.

People have lives.

That's not what this was about.

It was the pattern.

The SAME pattern.

You came back.

You initiated this.

YOU swiped right on ME.

You told me you were trying to ease your way back into my life.

You gave me the speech about dating and courtship and marriage.

You apologized for not being there before.

You presented yourself as a man who had grown.

Okay.

Then show me.

Because at this age, I don't need promises about the man you're going to be.

I watch the man you are.

And apparently Mr. New Leaf had turned over a new leaf...

but that motherfucker flipped right back over.

Same tree.

Same branch.

Same leaf.

Different year.

And that's when I realized something about second chances.

History does not earn you more patience.

Sometimes history means you get LESS.

Because I already know what the warning signs look like on you.

I've seen this movie.

I know where the jump scares are.

You disappearing doesn't confuse me anymore.

Your inconsistency doesn't make me wonder what I did wrong.

I don't need to chase you.

I don't need another explanation.

I don't need another “I'm sorry.”

And I DAMN sure don't need to run behind your car while you're trying to drive away from me.

That woman doesn't live here anymore.

Because when you come back into somebody's life claiming you've changed, you don't get six months to prove you're still exactly the same.

Sometimes three days will do it.

Tuesday: two-hour conversation.

Wednesday: inconsistent communication.

Thursday: ignored.

Friday?

Blocked.

That's a sequence I DO believe in.

And unlike Mr. No Sequence from my last adventure, this man should appreciate that one.

Because I'm almost 48.

I don't have 30 minutes for bullshit anymore.

You know that old reality-show moment?

“Do you know you have 30 minutes?”

Baby, you don't even have that fucking long with me.

Not anymore.

I'm not asking anybody to text me every five minutes.

I'm not asking for a play-by-play of your day.

I'm not asking you to FaceTime me while you take a shit so I know you're alive.

I'm asking for consistency.

If you tell me Tuesday that you're intentionally trying to come back into my life, don't make me search for that intention on Wednesday.

If you say you're interested, act interested.

If you say you've changed, demonstrate change.

If you want to court me, then court me.

Because “good morning” isn't courtship.

A two-hour phone call isn't commitment.

And talking about marriage doesn't mean shit if your actions can't survive 48 hours.

Maybe Mr. New Leaf really has changed.

Maybe he's wonderful now.

Maybe he'll make somebody very happy.

I genuinely hope so.

But I don't date potential.

And I damn sure don't date press releases.

I date behavior.

His behavior answered the question before I ever had to ask it.

So I blocked him.

Quickly.

Quietly.

No dissertation.

No chasing.

No standing outside crying.

No almost getting my foot run over.

Just:

BLOCKED.

And you know what?

Maybe that's my new leaf.

Because sometimes growth isn't finally getting the person you wanted 15 years ago.

Sometimes growth is realizing you don't want the same shit anymore.

Even when it comes back wearing a new outfit.