Chapter 4 - Two Friends, One App: Hilarious Online Dating Stories We Did Not order

Armed with my therapist’s wisdom (and let’s be honest, a slightly delusional amount of optimism), I jumped right back into the upside-down carnival we call online dating.

This time, however, I wasn’t going in alone.

One of my girls from the tribe, Margot, decided to join me.

This is our story.

Margot

Single mom (one teenage boy)

Insurance expert.

Introvert.

Owner of a backside so impressive it deserves its own postal code.

Margot is the kind of woman who reads policy documents for fun but will absolutely destroy you in a pair of jeans. Naturally, the universe decided she needed a little adventure.

Enter: Sean.

Dating Sean

My first date with Sean was not what I expected.

We met at a bowling alley. In between knocking down balls, I looked at him and damn did he have nice eyes. As a matter of fact, he had the most beautiful eyes I had ever seen. The conversation? Elite. Effortless. The kind where you think, Oh no… I might like this one.

An hour in, he looked at me with determination and declared he wanted to cook for me.

I assumed he meant next week.

He did not mean next week.

He meant that night.

Ladies… I went with it. Please don’t judge me.

We went to the grocery store, where I watched this man examine vegetables like he was judging a produce pageant. He smelled basil. He squeezed avocados with authority. I knew then and there: this was a foodie.

He insisted on cooking while I watched and refused my help. He lived in a charming little cottage. Yes — he owned his own house. A man with property and knife skills. I was practically picking out curtains in my head.

The meal? Spectacular.

I called Chris right after dinner and we giggled like schoolgirls. This was the beginning of three weeks of pure bliss:

• Morning messages.

• Endless conversations.

• He told his family about me

• Showed up unexpectedly just to spend a few minutes in my company before heading back to work.

• Dinners.

• Breakfasts.

• Outings.

Hope.

And then…

Silence.

Not “busy at work” silence.

Not “phone died” silence.

Deafening. Unsettling. Echoing silence.

I called. I texted. I gave him space. I journaled. I consulted the tribe. I replayed every conversation like it was game footage.

I am not an overthinker — but I do have an advanced degree in emotional forensics when necessary.

My friends told me to forget it. But peace of mind is priceless, so I called one more time.

He answered.

He was confused. Did not know what he wanted anymore. He chose to take a leave of absence from work… and from me.

I sat with that.

Compassion and disappointment can exist in the same body. That was a new lesson.

The tribe helped me rebuild my confidence, and reminded me that I am, in fact, a catch.

So I went back out there.

Then There Was Dean

Dean was tall. Great smile. Good conversation. We met for coffee and cake — low stakes, low pressure.

The date was pleasant. Respectable. Mildly promising.

Then the waiter came with the bill.

Assuming Dean was paying, the waiter had already processed the charge on his credit card before either of us could speak.

Dean immediately turned to me and asked for my half.

$15.

Now, I am fully capable of paying my share. I believe in equality. I am a modern woman.

What I did not expect was to be treated like a dine-and-dash suspect over cheesecake.

Since I didn’t have cash, I offered to send an e-transfer. He agreed.

I stood up to leave.

He politely — but firmly — forbade me from exiting the coffee shop until he physically saw the transfer land in his account.

I showed him the confirmation.

Still, we waited.

Ten full minutes of romance marinating in financial distrust.

When the funds finally cleared, I walked out of that café feeling like I had just completed a small claims court settlement.

He called a few times afterward.

I did not return the calls.

Some love stories end because of incompatibility.

Others end because you refuse to live your life providing real-time banking updates.

Bob the Baker

Bob the Baker was next.

Nice guy. Cute.

Emotionally unavailable.

Ah yes. My specialty.

Bob made croissants that could heal nations, but when it came to emotional presence? Closed for renovations.

I left that situation with carbs and clarity.

Honestly, not my worst trade.

Through this round on online dating, I learned that chemistry is not compatibility.

That charm is not character.

That a man who owns a cottage can still disappear.

And that $15 is a small price to pay for a crystal-clear red flag.

Mostly, I learned this:

Dating in midlife isn’t about finding someone to complete you.

It’s about meeting people from a place where you are already whole.

And if the worst-case scenario is a good story, a stronger backbone, and a tribe that will pump your tires when needed?

Well.

That’s not failure.

That’s research.

Back to you, Chris.

Chris

Mick… not what I ordered.

Mick had the greatest pictures ever.

Stylish.

Slicked hair.

Perfect five-o’clock shadow.

Broad shoulders.

Promising. Very promising.

We agreed to meet at a coffee shop. He was already there when I pulled into the parking lot.

And there he was.

He vaguely resembled his pictures… if his pictures had been taken during the Bush

administration.

I immediately texted my BFF:

Call me in 45 minutes so I know it’s time to leave. I will not answer. But I expect a call. This is not a drill.

I schooled my face into what I hoped was “pleasantly neutral” and walked toward him.

He stood up.

He was about 6’5. Imposing. Towering.

His hair was not slicked with gel.

It was slicked with… life.

The kind of natural grease that can only be achieved through several days of avoiding shampoo. The kind of grease that has history. I swear I could smell it before I even sat down.

I sat anyway. Because I am nothing if not polite. And occasionally optimistic to the point of self-harm.

We talked about work. Children. Childhood memories.

But as he spoke, he became increasingly animated. His voice grew louder. His gestures sharper. He looked less like a charming date and more like a man about to deliver a manifesto.

The men at the neighboring table looked at me.

Not casually.

Intentionally.

Their eyes said, Are you safe? Do you need extraction? We can create a diversion.

I held strong.

This was, without question, the longest 45 minutes ever recorded in human history.

And then… salvation.

My phone rang.

Mick looked concerned.

“Is it the kids?”

“Yes,” I said, with the calm authority of a woman who had just been handed her freedom papers.

I stood, walked to the counter, and paid the full bill.

Mick looked both shocked and delighted. He had just witnessed a rare and mystical phenomenon: a woman paying to escape.

We hugged.

His hair got dangerously close to my face.

I survived.

The moment I got into my car, I called my BFF and screamed until my lungs filed a formal complaint.

How unlucky can one girl be?

When I got home, I messaged him to thank him for meeting me and wished him luck in finding the right person.

He was surprised.

I was free.

And then came Rob.

Athletic. Outdoorsy. Disciplined. Worked out every day without fail. Had a great job.

We messaged every day for a week.

Chemistry. Wit. Momentum.

And then…

Nothing.

He disappeared without warning. No explanation. No goodbye.

Gone.

Like Casper.

Except Casper had the decency to remain friendly.

The next contestant… drum roll… Sammy.

Divorced. Two kids.

And an ex-wife apparently responsible for world hunger, global warming, and the collapse of civilization.

He spoke of her with passion. Intensity. Commitment.

I nodded politely while mentally rearranging my furniture and wondering if it was too late to become a nun.

Along came Johnny.

The conversation was effortless. Easy. Natural.

Until he found out how old my children were.

Too old, apparently.

Too old for his carefully curated vision of a woman whose life had left no visible marks.

Too old for him.

Ouch!

Somewhere between the grease, the ghosting, and the trauma-dumping, I realized something important.

I was awake.

Awake to the difference between attention and intention.

Awake to the difference between being chosen and being valued.

Awake to the quiet power of walking away.

I was eliminating.

And once you’re awake, you never go back to accepting less than you deserve.

So….

Margot still meets interesting men.

I still meet… educational ones.

We still exchange post-date debriefs like FBI agents reviewing case files.

We still believe. Carefully.