Dear Jack: I’ve Been Writing You Letters Every Week for Over 10 Years, But You’re Not Even 10 Years Old Yet…

9 years, 7 months.

Dear Jack,

It was May 2010 that I decided to start writing you at least one letter every week, to serve as a thumbnail of what was going on in your life that week, or at least what was going on in my head as your dad that week.

I should point out that in May 2010, you weren’t born yet. Instead, that was the month that Mommy and I found out we were going to be having a baby.

You weren’t born until November. So for over a decade, I have been creating and growing this collection of journal entries to document each week of your life.

I have told you about it. You are aware I do this.

But later, when you are older, I think you will truly be able to appreciate having an archive of your own life, written by your dad.




Dear Holly: How Many More Years Before You Can Drink Coffee Too?

4 years, 1 month.

Dear Holly,

It is pretty much a daily conversation at our house. You say to me, “Daddy, when I’m older, I can drink coffee too.”

During the month and a half I was home from my job on furlough, which ended last week, you watched me everyday in the morning and afternoon, as I made myself instant black coffee.

Not to mention, you and brother join Mommy and me at whatever coffee shop we end up on the weekends.

I see Starbacks Frappucinos in your future. We just now let your brother start drinking the non-coffee flavors, and he’s 9 and a half.

You still have several more years, it sounds like.




Dear Jack: Your Request for “Direct Deposit” Whipped Cream

9 years, 6 months.

Dear Jack,

As Mommy was setting up everyone’s plates for the special strawberry shortcake she surprised us with over the weekend, the only thing you were interested in was the can of whipped cream.

You asked Mommy, “Can you just spray the whipped cream right in my mouth?”

To my surprise, she did.

You were very pleased.

The funny thing is, I’m not convinced you actually ate the actual dessert.

Where as your sister copied you, to get the “direct deposit” whipped cream, she definitely ate the strawberry cake too.

I thought the concept of a drive-thru window was lazy, but this takes it to a whole different level!



Dear Jack: Jumping on the Trampoline with Papa, Like 2 Kids

9 years, 5 months.

Dear Jack,

I enjoy looking out the window and seeing you jumping on the trampoline with Papa; specifically now that he is retired.

It reminds me of 30 years ago when I was your age and he would jump with me.

I’m glad he enjoys jumping with you, because for some reason, after I stopped being a kid, it started making me too dizzy and disoriented to jump on a trampoline anymore.

When I see the two of you jumping together, it makes me think of the song I recently wrote, called “These are the Good Ole Days”.

It is important to recognize how fortunate we are, even if in the moment, it doesn’t seem like we are in the good ole days; because we probably are.



Dear Holly: Your Framed Picture of You and Your Cousin

4 years old.

Dear Holly,

For your 4th birthday last weekend, we had a small party for you with family; only 10 people.

Until the COVID-19 lockdown, we had a big birthday planned for you at the park- there was going to be pony rides!

I guess we’ll be saving that plan for when you turn five next year.

But still, your 4th birthday party was very special because we got to spend it with your grandparents and cousins on my side of the family; at least.

A very special gift you received from your cousin Darla is a picture of the two of you together; which is now propped up on your night stand right next to your bed.

It means a lot to you, as the two of you are inseparable anytime you are both together!