The Text Message That Got Me 3 Dates in One Week

At 55, I’d given up on dating apps. My last attempt ended with a 28-year-old asking if I was “my daughter’s dad.” I deleted the app and poured myself a whiskey, convinced my romantic life was over.

Then my nephew—bless his Gen-Z heart—sat me down. “Uncle Rick,” he said, “it’s not you. It’s your texts. You sound like a LinkedIn profile.”

He was right. My opener? “Hey, how’s it going?” My follow-up? “You seem nice.” No wonder I was ghosted.

So I rewrote my approach. Not to be slick—but to be human. And one message changed everything.

It started with Sarah. Her profile said: “Love old jazz, rainy Sundays, and men who know how to listen.”

Instead of “Hey,” I wrote:

“Saw your photo at the record store—was that ‘Kind of Blue’ in your bag? If so, you’ve got excellent taste… and I owe you a drink for reminding me why Miles Davis still matters.”

She replied in 12 minutes: “It was. And I’ll take that drink—but only if you promise not to talk about your 401(k).”

That night, we texted for two hours. Not about jobs or exes, but about the first album that made us cry, the smell of old books, and why Casablanca is the ultimate love story.

We met three days later at a jazz bar. She wore red lipstick and a smile that said she’d already decided she liked me. Over bourbon, she leaned in and said, “You text like a man who’s lived. Not like you’re trying to sell me something.”

That week, I went on three dates—all from that same messaging philosophy.

Here’s what I learned:

1. Specificity is sexy.
“Hey” is forgettable. But “I saw your photo at the farmers market—was that heirloom tomato as good as it looked?” shows you saw her, not just her profile.

2. Lead with curiosity, not need.
Don’t ask, “Do you like me?” Ask, “What’s the last thing that made you laugh out loud?” It invites her to share, not perform.

3. Humor disarms.
After my second date, I texted: “Just so you know, I practiced opening your car door all night. My cat was unimpressed.” She replied with a laughing emoji—and a “See you Friday?”

4. Silence is okay.
I used to panic if she didn’t reply in an hour. Now I wait. Real connection breathes. It doesn’t suffocate.

5. End with warmth, not pressure.
Instead of “When can I see you again?” try: “Tonight reminded me how much I love talking to someone who gets it. No rush—but I’d love to do it again.”

The women I met weren’t looking for perfection. They were looking for presence. A man who wasn’t trying to be 30 again—but was proud to be exactly who he is at 55.

One told me, “Most guys my age are still playing games. You? You just showed up as yourself.”

That’s the secret.

You don’t need better photos or a younger bio. You need to speak like a man who knows his worth—because you’ve earned it.

So next time you open that app, don’t ask “How’s it going?”
Ask something only she can answer.
And watch what happens.

Because desire isn’t about age.
It’s about attention.
And you, my friend, have a lifetime of it to give.