Chapter 7: My Midlife Speed Dating Adventure: Laughs, Awkward Pauses, and Unexpected Plot Twists

Getting divorced in midlife is a special kind of plot twist.

Because suddenly… you’re single.

And everyone else you know is still very much married.

Maybe there’s one or two others in your circle going through it too—but for the most part, you’re the outlier. The one people look at with curiosity. The unofficial field reporter of modern dating.

And your married friends? They mean well. They really do.

But they got married when flip phones were still a thing. They have no idea what’s happening out here.

Honestly? Neither do I.

Which is why, when my coworker Mel—freshly divorced, slightly younger, and alarmingly enthusiastic—found a “top-tier” speed dating event, I said yes.

Not because I believed I’d meet the love of my life.

But because… content.

Now this wasn’t your average speed dating situation. Oh no. This was curated.

There was a questionnaire.

There were deal breakers.

There was a full-on interview.

I ended up on a 30-minute call with one half of a husband-and-wife “dating coach” duo, answering questions like:

“Are you open to interracial dating?”

Yes.

“Do you mind if your partner smokes?”

Depends. Cigarettes? Maybe. Emotional baggage? Hard no.

Then they asked for a photo.

I declined.

Let’s not get ahead of ourselves.

The day of the event, Mel and I prepared like we were heading to the Met Gala of poor decisions.

Hair done.

Makeup done.

Nails done.

Outfits carefully selected to say: “Effortless, but also… I tried.”

We arrived, got in line—and immediately started bonding with other women. Including, of course, my former Zumba instructor. Because nothing says “new beginning” like sweating to reggaeton with someone and then seeing them at speed dating.

And that’s when I noticed something.

Where… are the men?

Because the ratio was giving Bridesmaids: The Convention.

Still, I thought—okay. Stay open. Stay curious. You came for the experience.

Inside, I’ll admit—it was nice. Chic venue, DJ, low lighting. Very “you might meet someone” energy.

We were handed index cards with names and table numbers. One minute per man.

One minute.

I’ve spent longer deciding on salad dressing.

Before things started, there was a cocktail hour where we were encouraged to mingle.

In theory.

In reality? It was a middle school dance.

Women on one side.

Men on the other.

Everyone pretending to check their phones like they had somewhere else to be.

Growth.

Then the rotations began.

Man #1: handsome, polished, promising.

We start talking… and then I see it.

The shift.

You know the one. The subtle “processing” face. Like his brain is buffering and then lands on: Hmm… maybe not.

Sir, we’ve been speaking for 42 seconds.

Relax.

Man #2: also attractive… but emotionally mid-breakdown.

He spent our entire minute talking about his ex-wife and his divorce.

And I thought, I just got out of a marriage, not into a counseling practice.

Man #3: silent. Completely silent.

I was performing. Hosting. Producing. Carrying the entire conversation like it was a one-woman show.

Also, I’m fairly certain he had at least 20 years on me.

Respectfully… no.

Man #4: didn’t show up.

Which, honestly, felt on brand at that point.

So I sat there and observed.

And what I saw was a room full of beautiful, intelligent women doing the polite smile… while slowly realizing they had been sold a slightly upgraded version of disappointment.

Meanwhile, the organizers were moving fast, a little too fast… like people trying to fix a situation in real time.

Translation: there were not enough men.

Man #5: kind, interesting, normal.

We exchanged numbers… as friends.

He lived in the Bahamas and was in town for the summer, which already sounded like a better plan than anything happening in that room.

And that was it.

No sparks.

No butterflies.

Just vibes… and not the good kind.

But here’s the part that stayed with me.

That look I saw from Man #1. The look I often see from men I meet. The look single women I speak to tell me about.

The initial interest… followed by the quiet realization.

She’s a lot.

Not in a bad way. Just… a lot.

Accomplished. Independent. Established.

Owns her home. Knows herself. Has opinions.

And somewhere along the line, that becomes intimidating instead of attractive.

Like I’m not “too much”—I’m just not conveniently sized.

Now here’s the twist.

The women who did upload photos? Stunning. Confident. Some went full “let me help you make a decision.”

They had the most matches on paper.

Seven. Eight. Nine.

And still… they left alone.

As we walked out, the “35 and under” group of women was arriving.

To meet the exact same men.

Same lineup. Different shift.

At that point, the seven of us who had bonded earlier looked at each other like:

“…we’re not going home like this.”

So we didn’t.

We found a Greek restaurant, walked in like we had a reservation (we did not), and took over a table.

And that’s when the night actually began.

We laughed.

We shared stories.

We ate incredible food.

We flirted—with the waiters, with each other, with life in general.

At one point, I’m pretty sure no one in that restaurant was safe.

We were the most fun table in the room.

And that’s when it hit me.

Not during the one-minute conversations.

Not while scanning a room that felt slightly off-balance.

Not even when I realized we were about to be replaced by the next group of hopeful women.

It hit me there—between the laughter, the shared stories, and the ease of being fully myself.

Because for the first time that night, nothing felt forced.

No performing.

No shrinking.

No trying to fit into someone else’s idea of “just enough.”

And maybe that’s what made everything else feel so… off.

And I left with more than I expected.

Not a match. Not a spark.

But questions.

Real ones.

About what dating looks like now… and whether there’s still space for women like me in it.

Women who have lived, built, lost—and rebuilt again.

Because somewhere along the way, it started to feel like those things—

the very things I’m most proud of—

might also be the things that make me harder to choose.

And I’m still sitting with that.

Not because I want to shrink…

but because I’m trying to understand the rules of a game I never expected to play again.

And still—

I didn’t get a date.

But I did get five new friends, a great meal, and a reminder that I can still walk into a room, take up space, and have a damn good time.

And THAT feels like a better return on investment than anything that happened at those tables.

Because if the takeaway is that I’m “too much”—

too established, too independent, too self-aware—

then maybe the real issue isn’t that I’m too much.

It’s that the room was too small.

Your turn:

Have you ever walked into a situation expecting one thing and walked out with something completely different — and better? Whether it’s speed dating, a first date, or just a night out that took an unexpected turn, I want to hear your story. Drop it in the comments — and if you’ve ever been told you’re “too much,” know that you’re in very good company. 😊