I’m an overthinker, I think.

In the past I’ve overanalyzed some of the most innocuous conversations—not what the other person said, but what I said (or didn’t say). I touched on it a bit here a year and a half ago.

What if they thought I meant this but I really meant that other thing? What if I unknowingly offended them? What if I, however unintentionally, hurt their feelings?

I do my best to put myself in other people’s shoes, consider situations from perspectives different from my own. Most of the time, this is a good thing. It helps me to hold my tongue in situations when I might be tempted to spout opinions that could potentially be hurtful or damaging, and (I hope) enables me to be a little more gracious to the people around me.

Other times, I get so wrapped up in the what if this, what if that, that I completely freeze. Use words, Rebekah. Speak! **crickets**

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You know all those “Things to never say to (fill in the blank)” articles on the internet these days? Those articles (I’m being generous calling them articles) make me feel crazy. Never, ever, ever say any of these 4 or 8 or 19 things to a new mom / a mom with a lot of kids / a mom of an only child / a pregnant woman / a single person / an extrovert / an introvert / a man / a woman / I could keep adding to this list for a while. There are loads of them. Type “what not to say to” into the Google search bar, and watch the list populate.

How in the world am I supposed to keep up with all of these rules so as to never accidentally offend someone? I’m already cautious with my words, but lists like that leave me feeling chained and silenced. Can someone tell me what exactly I am allowed to say or ask?

***

Several years ago, I ran into a then-acquaintance (now a friend) in the preschool parking lot. I was on my way to work after dropping off my daughter, and she was headed back home to her other kids after dropping off her son. I was wearing a button-down shirt, neat pencil skirt, and ballet flats. She was wearing exercise clothes. And when we stopped to chat for a minute and she complimented my attire, I said, “Oh, thanks!” and shrugged. And then I looked at what she was wearing and said, “I wish I could be home in my gym clothes right now.”

What it sounded like (insulting? condescending? jealous?) wasn’t what I intended at all. She just looked so comfy and chill, and I felt like a stressed-out preschool mom who was late for work—and she knew that. I, on the other hand, got back into my car, face aflame, and rested my forehead on the steering wheel. WHAT did I just say? Did I just imply that I think she has a cushy gig as a stay-at-home mom, sitting around in yoga pants and drinking coffee while I have to slog off to the office? I immediately began drafting an apology note in Facebook Messenger to clear things up, ’cause that’s what I do.

Turned out she hadn’t been offended in the slightest. She laughed and waved off the whole thing. She got it. Thank God for people who understand that we are all human.

***

I met a new(ish) friend for dinner the other night. As I drove to the restaurant, I wondered if it would be a quiet meal. Two introverts trying to get to know each other can be interesting sometimes.

My thoughts were way off base. Our meal wasn’t quiet at all. Three hours and two glasses of Pepsi each later, we only decided to wrap it up because we figured our husbands might be wondering what happened to us. We shared stories, asked questions, admitted our flaws, talked about some hard things, and laughed a lot. I went home feeling filled up and encouraged instead of drained.

And I didn’t mentally critique my end of the conversation later, like I sometimes do.

I’m trying to pin down what made it different. The game changer, I think, was honesty. I was able to speak freely and openly right off the bat because she started the conversation that way. No pretense, no pretending. And that made me feel safe to do the same. We both dove in.

Honesty starts a chain reaction. You open up to me, I open up to you; I open up to someone else, they feel encouraged to do the same. The process reaffirms faith, reveals bits of God’s bigger story, and builds authentic community.

***

People who understand and offer grace when what’s in my head comes out of my mouth all wrong? They set me free. Honest, real-life conversations set me free. Wouldn’t it be great if we did less list-writing and had more of those instead?

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Click here to see all posts from the Grace, Freedom, & the Rules series.

{This series is part of the Write 31 Days challenge.}