parenting

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Dear Jack: A Buddy Who Looks Up to You

14 years, 10 months.

Dear Jack,

After last week’s 3rd Saturday Cruise-In was cancelled at the last minute due to rain, you and your sister both still wanted to get out and do something. We had already planned to see our family friends, the McDaniels, there.

Mommy suggested Cracker Barrel instead, so that’s where we all ended up.

Just like a few weeks ago when we had them over at our house for dinner, their young son Walter buddied up to you.

After we ordered our food, you entertained him by playing him at that peg game they always have there on the table. And after dinner, he apparently taught you how to play checkers?

Your composure around him is so laughably nonchalant, yet still I can tell he thinks you’re really cool to hang out with.

Love,

Daddy

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Dear Jack: Your Instant New Hat Collection

14 years, 9 months.

Dear Jack,

This past Sunday, our family was invited to attend the big work party that Mommy was responsible for planning and directing.

When she explained there would be a “hat bar”, I just couldn’t comprehend what that even meant.

Once the party started, I suggested that our family be the first to try it out. I never would have imagined it would be so much fun to curate a collection of patches to be pressed on to a trucker hat. You immediately chose a Dale Earnhardt patch for your designated hat, as we assumed we would only get to make one hat per person.

But by the end of the party, since the cost of the hats and service were already paid for, you had some extra fun in creating some silly hats.

I would love to actually see you wear them in public…

Love,

Daddy

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Dear Holly: Why There is a Roller Skate on Your New Hat

9 years, 3 months.

Dear Holly,

I’m sure I’ve pointed this out before, but I’m officially the person in our family who says “no”. It’s written into my DNA and therefore my role as the patriarch of our family.

Not only do I say “no” to questions like, “Can we get a pet dog?” and “Can we get a pool?”, but I also am the person who initiates what time we will go to an event and what time we will leave.

I’m the gatekeeper and the timekeeper. As I like to think, I keep things fun by creating and promoting the boundaries.

Accordingly, I make sure that you and your brother get to bed on time, and more importantly, get to sleep on time, each night.

It is of course your instinct to delay the bedtime process every single night: “I need a hair tie first… I need some water first… I need some lotion first… I need my stuffed animal first…”

I learned to proactively say, “Okay, Holly… it’s time to go take your shower. Before you do, I need you to go get your hair tie, your water, your lotion, your stuffed animal… your roller skates!”

Part of our nightly routine is for you to respond to my silly joke, “Daddy, I don’t need roller skates to go to bed!”

So when it came time for you to create your trucker hat this past weekend at the “hat bar” at Mommy’s work party, in addition to the shell I suggested to represent our last name, you obviously also chose to include a roller skate patch!

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 Jack: Your New UTV “Side-By-Side”

14 years, 9 months.

Dear Jack,

It’s funny what you can order from Walmart’s website these days. When we were planning the move to Alabama back in late 2023, Mommy proposed the idea of our family getting a golf cart; since the neighborhood we now live in is adjacent to the golf course.

But once we got here, you realized that all your friends ride around in UTV’s (“utility task vehicle”), also known as a “side-by-side”.

Just a week or so after we ordered it from Walmart.com, a truck delivered our new side-by-side in front of our house.

I say “our” new side-by-side, but we all know it’s really yours. We’ve had a lot of fun already, simply exploring old trails near our house.

And I appreciate that you driving your side-by-side serves as great practice for you getting your driver’s permit here in a few months!

Love,

Daddy