parenting

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Dear Jack: Being the Official Entertainment of Sleepovers

14 years, 10 months.

Dear Jack,

You have made it clear that I have a reputation, as a dad, of being extremely strict when it comes to bedtime routine at our house. (That’s something I am very proud of!)

I’m all about having fun and experiencing adventure during daylight hours, but once the sun starts going down… it’s time to settle down.

But, hey… when I’m not there with you, I don’t care what time you go to sleep or how rowdy you get! Not my problem.

And that is exactly how I felt as Nonna sent me photos of you, your sister, and your cousin at their house while Mommy and I went away for a weekend trip a couple of weeks ago.

I was happy for all of you! You definitely served as the entertainment, making the sleepover even more exciting for your sister and cousin.

So much for setting down that night.

Love,

Daddy

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Dear Holly: What You Do at Sleepovers as a 9 Year-Old

9 years, 4 months.

Dear Holly,

I am still not over the fact that Mommy and I are at the point in life where she and I can just go away for a weekend, leaving you and your brother at Nonna and Papa’s… and it’s totally okay with everybody!

And it helps even more that your cousin Darla joined in at your most recent sleepover, ensuring that there would be nonstop 9 year-old activities the whole time!

Of course, much of it revolves around your collection of dolls… as the event becomes “the dolls’ sleepover” perhaps more than your own, as you perceive it.

I love it that we live in the same state as family now!

Love,

Daddy

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Dear Jack: You Started High School This Week

14 years, 9 months.

Dear Jack,

This is the question that came to my mind this week:

“Am I really old enough to have a kid in high school?!”

I mean… I guess I am. I’m 44. The math checks out. I was 29 when you were born.

So now, here in the fall of 2025, you have now started high school!

Something I am specifically excited about is that on your schedule for your freshman year, you have “Personal Finance” your 1st semester, then “Career Preparedness” your 2nd semester.

I feel you will be attending a progressive high school that will lead you to a bright future.

After all, I would know: I graduated from the same high school in 1999!

Love,

Daddy

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Dear Holly: You Started 4th Grade This Week

9 years, 3 months.

Dear Holly,

After a short summer of hanging out with your cousin Darla, the two of you now begin 4th grade together. But this time, you will be in separate classrooms, unlike last year when you were still a new student here.

But you are smart, confident, and friendly; so I know when you will easily make friends in your 4th grade class. Perhaps there will be new students who you help welcome to the school, now that you are settled in.

Though you won’t have your cousin right next to you the whole time this year, she’ll still be in the same hall; the classroom next to yours, actually.

I loved 4th grade! I think you will too.

Love,

Daddy

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Dear Holly: Trading in Your Pink Surfer Girl Jeep

9 years, 3 months.

Dear Holly,

I admit. It was sad to see your pink “Surfer Girl” Jeep out by the side of the road to be picked up; along with your old car booster seat and the stroller we used to push you around in. And for the record, someone picked it all up before we even went to bed that night.

The pink Jeep was your main gift from us for Christmas 2020; over 4 and a half years ago when you were only 4 years old.

And you certainly got so much use out of it all these years. It served its purpose, for sure!

But, I have to accept that you are growing up and that means you eventually outgrow certain toys. Now, your brother’s new “side-by-side” vehicle serves as the new upgrade to your pink Jeep!

 

Love,

Daddy