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How long has it been since your underwear was too cute to cover up?

Posted by on November 29, 2011 at 9:12 am

This fall, my sister visited and it became clear on that visit that my kids’ underwear was not up to snuff. I’m usually just happy that they are wearing underwear, so I never gave it too much thought. It takes the experience of an older sister to make one’s errors crystal clear.

Because we are from the midwest, we mention most things on the sly. Which is how she approached my son, Jake’s, undergarments.

My sister, noting Jake’s super hero briefs:  Has Jake tried boxers?

Me:  I don’t think so.

My sister, nodding once with raised eyebrows: Hmm.  I think he would like them.

Of course, I trotted out and picked up tw0 3-packs of boxer shorts for Jake. They seem giant but they’re cute and he was very excited about wearing them to bed.

Confident that we had hit a winner, I suggested that he wear them to school one day.

Jake:  Boxing shorts to school? That’s crazy.

Me: Crazy why? I don’t think so.

Jake: I’m not wearing them under my clothes. That’s crazy.

Me: But it’s underwear. You’re supposed to wear it under your clothes.

Jake:  Under my pants?

Me: Yes, I promise. Ask Daddy. Or your cousin. I swear.

Jake, looking at himself in his boxers:  Nice.

Since in our last underwear conversation, he had insisted on wearing his sister’s Hello Kittys, I felt good about the “boxing shorts” progress. And the boxing shorts are pretty cute. Of course, if he takes his pants off once he gets to school, I’m sure the teachers will be sending a note home about it. Yet another item that will never make it into his baby book, because, predictably, he doesn’t have one.

Filed under Expectations, Underwear
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