Awkward Encounters and Unexpected Kindness: A Day in the Life of an Awkward Mom

Just Another Day in the Life of an Awkward Mom

I’ve always been an awkward individual, and aging has only made it more obvious. Back in high school, I had a keychain that said, “I smile because I have no idea what’s going on.” All my friends agreed it was perfect.

Decades later, not much has changed.

Some days I still feel like I’m just one step away from someone jumping out and yelling, “Smile, you’re on Candid Camera!” (Does anyone even remember that show?)

For me, social awkwardness comes down to two main things:

  • A complete lack of awareness in public spaces
  • A deep, lifelong dislike of small talk

Ironically, those two traits make me a magnet for it. And not easy small talk, either – weirdly personal, oddly intimate small talk.

People tell me things. Strangers open up about their relationships. Cashiers linger. Random shoppers ask for my opinion on home décor. Why me? I still have no idea.

But this week, two very on-brand interactions reminded me that awkward people often attract the most unexpected moments.


Day One: The Lost Child

I was wandering through a store, circling a sturdy craft table for my daughter, when a quiet “Excuse me” stopped me.

A young girl stood there, tears filling her eyes.

She asked, “Have you seen a lady in a red T-shirt with dark hair in a bun?”

When I said no, she nodded bravely and whispered that she’d lost her mom.

We walked the aisles together until she spotted her. The relief and tears hit all at once as she ran back to her mother.

It wasn’t awkward – it was touching.

Later, I told my daughter how proud I was of that girl: for remembering details, for asking for help, for handling something scary with courage.

Why me? I don’t know. But I’m glad she chose me.


Day Two: The Checkout Compliment

The next day, my daughter and I were shopping for craft supplies when the cashier started chatting about our cat-themed beads. Mid-conversation, she suddenly said:

“And you’re pretty.”

That was it. No lead-up, no follow-up – just fact.

I blinked, looked for the hidden camera (as usual), and awkwardly laughed. I even asked her to repeat it, convinced I’d misheard.

But no – she doubled down. “You’re pretty.”

After a flustered thank-you, I mumbled something like, “You’re pretty too!” and escaped with my receipt.

Here’s the thing, though: maybe we should all do that more often.

I compliment people’s hair or earrings all the time, but I don’t think I’ve ever looked a stranger in the eye and said, “You’re pretty.” It felt awkward – and kind of wonderful.

Will I become that confident woman who wears dresses to the grocery store and boldly compliments others? Probably not.

But maybe it’s something to aspire to.


Maybe Awkward People Attract Weird Magic

Do these things happen to anyone else?

Is awkwardness some kind of beacon for unexpected human connection – like how dogs seem magnetically drawn to the one person in the room who’s not a dog person?

I don’t know. But I’m learning to appreciate it.

If you’ve had your own strange, sweet, awkward little moments, I’d love to hear about them. Drop a comment below so I know I’m not the only one attracting faux plant consultations and surprise compliments in checkout lines.


If you love honest, relatable mom moments (and awkward ones too), join my email list for stories that’ll make you laugh, sigh, and feel a little less alone.


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