The Mid Life Dating Files 2025

✨🍷Dating, Mixed Signals, and the Art of Trying to Read People🍷✨

Dating and figuring people out is hard. Really hard.

It’s hard to understand intentions. Hard to know what someone is thinking. And these days, it feels even harder because everyone wants to text instead of actually talking on the phone or — heaven forbid — sitting face-to-face. Text messages leave too much room for interpretation. You can’t hear tone. You can’t see facial expressions. You don’t get the pauses, the laughs, the hesitation — all the things that help you truly read a person.

And the truth is, even beyond texting, people are just hard to read.

It’s especially difficult when you like someone. You can’t always control how you feel, even when they tell you they want to “take it slow.” Or as I jokingly say, “take it slow and all skate.”

Because here’s the thing — if you both like each other, why not just go with it?

If you’ve known each other for years…

If you’ve already built a friendship…

If you have a lot in common…

If you’re attracted to each other…

If you’re on the same level in life…

Then why not?

I struggle with the idea of “taking it slow” when two people already know each other so well. This isn’t a situation where we just met. We’ve talked for hours. We’ve shared our backgrounds, our lives, our stories. We’ve gone out — not once, not twice, but over several years. So when someone says they’re ready to find their person and settle down, but still hesitates, it leaves you wondering where you stand.

In this situation, the hesitation comes from parenting — specifically, wanting to protect a child and not bring someone into their life too soon. I understand that. I truly do. Parenting is serious, and children come first.

But here’s the reality: the child is 17. Not 7. Not 10. Seventeen. He has a mother. And he has even told his dad that he wants him to have someone in his life.

At some point, life still has to be lived.

I’ve even said to him, gently but honestly, that it feels like he’s wasting his life — or at least putting it on hold. He has every right to live fully, to love, to be happy, to build something meaningful with someone. Parenthood doesn’t mean pressing pause on your own happiness forever.

And that’s where the real question comes in — is it fair to keep someone hanging on?

What is a girl supposed to do in a situation like this? When you like someone. When the attraction is mutual. When you know it is. When you’ve been dancing around each other for six years.

I finally said it out loud: This feels like a cat-and-mouse game.

So why keep playing it if we already know the outcome? Why keep circling each other instead of moving forward? Why “take it slow” when the foundation is already there?

When you already know each other’s past, values, and lives…

When you’ve talked endlessly…

When you didn’t just meet yesterday…

So what’s the deal?

The Takeaway

Maybe the real lesson in all of this isn’t about patience or timing — maybe it’s about clarity.

Liking someone isn’t enough. Attraction isn’t enough. History isn’t enough. Even years of connection aren’t enough if one person is moving forward and the other is standing still.

At some point, “taking it slow” starts to feel less like caution and more like avoidance. And while understanding someone else’s situation matters, so does honoring your own heart and your own time.

Because wanting more isn’t asking for too much — it’s asking the right person. And the right person won’t keep you guessing, waiting, or questioning where you stand.

Sometimes the bravest thing a girl can do isn’t holding on…

✨It’s deciding whether she’s willing to keep waiting for someone who may never be ready to meet her where she is.✨