The Mid Life Dating Files 2025

Share one of the best gifts you’ve ever received.

One of the best gifts I’ve ever received didn’t come in a little blue box from Tiffany & Co..

Now let me clarify before anyone panics.

Yes, I do love the little blue box.

Yes, I have received the little blue box.

Yes, I believe the little blue box is always appropriate.

Sparkle is never wrong.

But one of the most unforgettable gifts I’ve ever received came with a boarding pass, ocean air, unlimited soft-serve ice cream… and my parents.

A cruise.

Actually… several cruises.

Because when your birthday lands in November—smack between Halloween and Christmas—your gifts get bundled into one efficient celebration.

“Happy Birthday and Merry Christmas! See you at the port.”

And those boarding passes?

They come with wine.

They come with margaritas.

And blessed be the beverage package… especially the one earned from the casino.

Because yes, we gamble like high rollers. (In spirit. Let’s not examine the spreadsheets.) We cruise so much that somehow we earn “free spirits” every single day.

Free drinks. Free fun. Free entertainment.

Aren’t we just the luckiest little cruisers?

And let’s just go ahead and be honest…

They come with wine.

And we also smuggle wine in our suitcases.

Every bag we can.

We love some wine.

If there’s an empty corner in a suitcase, Mom sees opportunity. I’m not saying we could open a small vineyard out of Cabin 8234… but I’m not saying we couldn’t either.

Now, I’d love to tell you our cruises are calm and relaxing.

They are not.

They are floating sitcoms.

My mother—Janet, also known as Janeto (a nickname she despises, which is exactly why I continue to use it)—is constant attention and commentary. Drama finds her. Or she finds it.

Someone cuts in the buffet line?

We now have a situation.

Someone saves chairs at the pool?

Oh, it’s a full investigation.

Meanwhile, my dad is delivering sarcasm like he’s on a comedy tour. His timing improves every year. He’ll drop a perfectly placed one-liner, and my mother slowly turns and gives him The Stanky Eye™.

And I sit between them.

Margarita in hand.

“Okay, you two. Hug it out.”

They never hug it out.

Dad goes to spin class several days a week and boards the ship like he’s training for something televised. Mom considers reaching for the remote cardio while watching the news and occasionally earning herself a brief stay in Facebook jail arguing with strangers she has never met.

Drama with Janeto is a year-round subscription.

She drives me crazy making me drive everywhere and narrating my parking like I just got my learner’s permit.

“Don’t park there.”

“That’s too far.”

“You’re crooked.”

Ma’am. I have grandchildren.

And yet later that evening, I’m keeping my bartending skills sharp beside the casino while Mom plays cards. If she’s playing, I’m pouring. It’s teamwork.

Between the sarcastic dad jokes, the dramatic buffet critiques, the casino “high roller” status, the blessed beverage packages, the suitcase wine operation, and the endless eye rolls, we are stacking up memories faster than cruise reward points.

And that’s really the gift.

Yes, I love the sparkle.

Yes, I love the wine.

Yes, I love the margaritas that appear once those boarding passes are scanned.

Yes, I love that we cruise enough to rack up free spirits daily.

But the greatest gift?

Time.

Time with parents who don’t look or act their age.

Time laughing at jokes that get better every year.

Time rolling our eyes together.

Time saying, “Okay, you two…” one more time.

Along with my children and grandchildren, my parents are truly some of the best gifts I’ve ever received.

Even if one of them is currently telling me I parked crooked.

And honestly?

I wouldn’t miss a minute of it.🍷🛳️