Say the Thing

Why the best friendships risk a little awkwardness

I recently read a book where the main character realized she had gone several hours on a very important, very public day with a piece of spinach stuck between her teeth. Not a dainty little fleck, either. A full leafy situation.

And none of her friends had told her.

Understandably, she was furious. At that point it’s not just spinach. It’s a conspiracy.

“What kind of friends ARE these women?” she demanded. “How could they let me walk around like this all day?”

Because there are few things more destabilizing than realizing you have been publicly existing… incorrectly. For hours.

As a reader, the scene was hilarious. Also deeply relatable. Because we’ve all had that moment when a friend’s action—or inaction—makes you pause and think: How could my friends DO this to me!

Just this past week, I posted on several MomCo Facebook pages (as part of my job as the MomCo Membership Manager) asking leaders to share how they went the extra mile with our theme, Make It Awkward, this year. I received several creative and funny responses, but one in particular stood out because it had me both laughing out loud and thinking long after.

One leader shared that at one of her MomCo meetings (of which there are usually between 20–50 women), she intentionally wore her shirt inside out and waited to see who would say something. If someone did, she pulled a mint out of her pocket as a prize and thanked them for “making it awkward.” In the end, about 25% of the group had the courage to say something before she revealed what she was doing.

When I first heard it, I howled. What a clever, funny way to bring this year’s theme to life. But the more I thought about it, the more I kept coming back to that 25%—the women who were brave enough to speak up.

Because it sounds easy, doesn’t it? And yet, in the moment, it’s often not easy at all. Like telling a friend she has spinach in her teeth knowing she will be super embarrassed afterwards.

Being awkward is hard.

I need to get something off my chest—I really stink at being awkward. Even when I know I NEED to say something to someone, for their own good, I often hesitate because more than anything I hate to embarrass people.

Time to confess something that has burdened me like a Catholic sin for several years: a woman came to my house for a party and -give me a minute to collect myself as I tell you this- her dress was tucked into her undies in the back. Full backside exposure. Like that famous dance scene in The Parent Trap.

I noticed it a few minutes after she arrived, as she headed to the drink table, and thought to myself:

“Oh. My. Lord. This. Is. Happening.”

And then guess what I did?

Nothing.

I was already feeling so much secondhand embarrassment for her (and she was still oblivious at this point) I felt like I was seeing into the future, knowing how absolutely mortified she would be when she realized her undergarment catastrophe. I should have walked right up to her and gently ushered her to the side, quietly whispering the truth to her before anyone else noticed.

But I didn’t. I froze.

And she walked across the room blissfully unaware.

Ten minutes later, I saw her again and her dress was pulled out and down where it belonged. I felt so much relief, you would have thought I was the one who had tucked her skirt into her undies in the first place.

It’s easy to laugh about it now, but I genuinely feel guilty when I think about it. I failed her as a fellow woman and member of humanity.

I fear that when my grandchildren climb up on my lap when I’m 99 and ask me if I have any regrets in life, I’ll tell this story.

“There goes Great Grandma again,” they’ll say, “muttering about some lady’s underpants.”

Which takes me back to this little inside-out shirt experiment.

Big kudos to the women in the room who had the guts to say something and make it awkward. But what about the 75% of them who saw something and said nothing, only to have her reveal at the end it was a fun little social experiment?

Do you think they regretted not saying something more or less after that? When they learned that their fear of making it awkward was actually the point of the entire thing?

Because this is what real friendship is all about, right? Digging a little deeper than the surface level, doing real life with each other in all its awkward glory.

Because it turns out friendship isn’t just long talks and group texts and remembering each other’s birthdays. Sometimes it’s this:

“Hey. I love you. And also your shirt is inside out.”

Or, if we are really growing as people:

“Hey. I love you. And we need to discuss what’s happening in the back of your outfit.”

It’s not glamorous. It’s not smooth. It will not make it into a curated Instagram caption.

But it might save someone from becoming someone else’s cautionary tale.

And maybe that’s what Make It Awkward was getting at all along. Not awkward for the sake of awkward, but awkward in service of something better—honesty, care, the quiet kind of courage that says something when it would be easier not to.

So here’s to the 25%.

May we become them.

And may we, for the love of all things good and decent, never again let a woman walk freely into a room with her skirt tucked into her underwear while we stand by silently, holding a drink and our own moral failure.