The Mid Life Dating Files 2025

How has a failure, or apparent failure, set you up for later success?

Failure, Red Flags, and Rewriting the Story (A Christy Blog)

People always ask that deep interview question: “How has a failure set you up for later success?”

And I’m always tempted to answer very honestly:

Which failure would you like to start with?

I’ve got a whole catalog.

Now don’t get me wrong — I try to learn from my mistakes. I really do. But sometimes I feel like I’ve misplaced my brain somewhere between Chapter 3 and Chapter 7 and I keep rereading the same chapter like it’s a brand-new plot twist.

You know the saying: If you keep doing the same thing, you’ll get the same results.

Well… apparently sometimes it takes me a few rounds to fully absorb the lesson. Especially when it comes to dating.

Oh yes. Let’s talk about my specialty: picking the wrong guys.

Some people have a talent for singing, cooking, or math.

My gift has been spotting red flags and thinking, “Hmm… that’s probably just festive decoration.”

But eventually you start to recognize the pattern.

You’re driving down the same road of life and suddenly you think:

Wait a minute…

Déjà vu.

What in The Who am I doing here again?

That’s when you slam the brakes, throw the car in reverse, and say:

“Okay, let’s rewrite this story.”

One of the biggest lessons came after my divorce following 26 years of marriage. That chapter taught me a lot about independence, strength, and learning to do life on my own terms.

And it also taught me an important relationship rule:

When the red flags are screaming directly in your face…

GIRL. RUN.

Don’t pause.

Don’t analyze.

Don’t think, “Maybe he’ll change.”

Just keep walking like you’re late for something important — because you are. Your peace.

I’ve learned lessons in friendships too. These days my circle is very small and very solid — more like concrete than a revolving door. I trust a few people deeply, and I’m okay with that.

Honestly, these days I’m perfectly happy being a bit of a hermit.

Most nights you’ll find me at home with my cat, Blaze, hosting what I call our kitchen cooking parties. Music is blaring, I’m experimenting with new recipes, and Blaze watches me like I’m the star of a cooking show that has completely gone off the rails.

Picture this:

Wine in one hand.

Wooden spoon in the other.

Music playing.

Me dancing around the kitchen while something questionable simmers on the stove.

Blaze just sits there like,

“This woman has absolutely lost it.”

But here’s the thing.

Every failure has taught me something.

Some lessons were gentle.

Some came in like a wrecking ball.

And I’m sure I’m still learning. Probably always will be.

That’s life.

You fall down.

You laugh about it later.

You get back up and try again — hopefully a little wiser the next time.

In the meantime, my advice is simple:

Drink good wine.

Cook good food.

Listen to great music.

And make this one life the best story you can possibly write.🍝🐈‍⬛🍷🎶