You Don’t Know Jack: A 3 Year Old Love Story

February on With Love and a Little Self-Deprecation is dedicated to love. Family love, friendship love, marriage love, “that wasn’t even close to being” love – just lots and lots of love. But in a funny way, I promise. Today’s My Funny Valentine post, a little man who stole my heart three years ago. 

I know a lot of funny people. My husband is funny. My friends are funny. My brother is funny (looking). But my son is hands down the funniest person I know and he’s only 3 years old. 3 years old this week in fact.

So in honor of my first born and all of his awesomeness, today’s post is all about sharing some great Jack moments from the past 365 days. From the insightful, to the goofy, to the downright savage, the thoughts this little man graces the world with keep me on my toes. And if this is just the stuff he says out loud, who knows what other gems are bouncing around in that brain of his.

My dear child, your wit is real gift. YOU are a real gift. Keep bringing the funny, the smart, the sweet, and shocking Jack. I love you all the way to the moon and back.

You don't know JackJack on Parents

“Mommy needs to focus, don’t worry about Jack.”

When I suggested that he pick out his own book and bring it back to the couch for me to read to him – “Come on little princess, you’re good at walking.”

“Mommy, you are my masterpiece.”

“You know what you do when you fall down, Daddy? You get back up and shake it off.”

Jack on Wine

“What’s that?” – Jack
“Well, it’s like juice for adults.” – Me
“Oh, is it wine?” – Jack

“Jack little bit bigger drink wine. Just one glass.”

You don't know Jack

Jack on Food

Sees a pizza on the ground in a parking lot – “Mommy, WHY WOULD THEY DO THAT???”

“I’m crushing this pie…”

“I have an idea! Let’s eat some chocolate.”

“Mommy, I almost didn’t like this dinner. But I did.”

Jack on being a Boston Kid

“I don’t want to go home. Want to go to Dunkin Donuts.”

“The Broncos aren’t on TV. They are playing golf somewhere.”

You don't know Jack

Jack on School

“How was school?” – Me
“Drama, drama…” – Jack

“What did you do at school today?” – Me
“Ugh, I don’t want to talk about it.” – Jack

(Editor’s Note: He loves school and calls me by his teacher’s name on a regular basis. He also refers to her as “his best girl.”)

Jack on Living His Best Life

“That’s NASTY! In a good context.”

“Slay all day!”


“I need a cricket! A cricket to help me! Or a squirrel.”

While being lifted up to get into his car seat he swung his legs on top of the roof and said “PARKOUR!”

You don't know Jack

Jack on Jokes

“Knock Knock”
“Who’s There?”
“Abby, Who?”
“Abby Birthday to you!! High Five!”

Jack on Being a Big Brother

Sits next to Norah on the floor and puts his arm around her “It’s tough, huh?”

“Come here, Norah honey. I’m in charge.”

“Hey Norah, do you want to go play with your dollhouse? Here you go, look, you want to play with your dollhouse. I’ll help you sit.” (Quickly exits to go play with all the toy cars, undisturbed.)

To me and Norah, “You are the ladies of my life.”

This entire interaction.

You don't know Jack

Jack on Being Savage

“Mommy, your hair messy. You gonna fix that?”

Peeks under bathroom stall at a rest stop – “Who’s tooting?”

“Mommy I’m going to tell you a long story. There once was a girl named Flora. She couldn’t find her family. The end.”

Happy Birthday, Jack! I love you!

With so much love for the future President of the World,

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