More Vulnerability, Less Perfection: A Throwback Dating Tip

When it comes to dating over 40, dating over 50, or even dating over 60, one of the most powerful qualities you can bring to the table—especially in the early stages—is vulnerability.

This Throwback Dating Tip is for everyone, but especially the gentlemen out there.

So often, there's pressure to show up as "perfect" on a first date—saying the right things, planning the ideal activity, and never missing a beat. But here's the truth: what builds trust isn’t perfection, it’s authenticity.

Let me share a quick story…

A friend of mine is recently divorced and getting back into the dating scene. He met a woman he genuinely admired and was thrilled when he finally got her number. Wanting to make a great impression, he held off on contacting her until he could come up with the perfect, unique idea for a first date.

But in the meantime, a few weeks passed—and by the time he reached out, the spark seemed to have faded. She was no longer showing much interest.

Soon after, he saw one of my videos: How Long Should You Wait Before Asking Her On A Date? It hit him—he’d waited too long.

We talked about it, and I encouraged him to do something bold: be honest. Here’s what I suggested he send:

“Hey, how have you been? I have a confession to make... I think you're an amazing woman and was really excited to take you on a date after I got your number. I wanted to impress you, so I spent time looking for something fun for us to do together—and by the time I reached back out, I feel like the spark was gone. I’m new at this dating thing, so I think I waited too long. But if you’re still open to it, I would love the opportunity to take you out.”

By simply sharing what was true for him, he not only demonstrated vulnerability, he showed integrity—and that’s what builds real connection.

If you're navigating the world of dating over 50 websites or trying to connect with someone new offline, don’t underestimate the power of being real. If a woman responds with understanding, that’s someone worth exploring something with. And if she doesn’t? You just saved yourself time and emotional energy.

Either way, you win.

So guys—and ladies too—remember: vulnerability isn’t weakness. It’s a doorway to trust, connection, and maybe even love.

Happy Dating!

❤️ Megan