Why you're not funny enough
I visited my younger daughter last weekend. She and her partner both overthink like crazy.
But you'd never know it to listen to their banter.
She said something that didn’t make sense, and her partner gave her the “whaaat?” look.
Her response? “Not my fault. You’re the one who stuck his dick in crazy.”
Humor feeds connection
Their ability to make each other laugh out loud is part of their relationship glue.
Pro tip: Laughter is a hot quality early in relationships because most people look for someone with a good sense of humor.
But overthinking gets in the way.
You think of something funny, but it dies in your head before it ever makes it out of your mouth.
Because you start analyzing. Will this be weird? What if they don’t get it?
By the time you decide it's safe, the moment has passed.
A surefire way to use humor
A quip about a shared experience short-circuits the analysis. There's no risk in naming what you both feel, whether it's awkwardness, uncertainty, or frustration.
This kind of humor creates connection because you're both in on the joke.
Like this:
You’re on a date. A lull in the conversation turns into silence that gets more awkward the longer it lasts. Instead of scrambling mentally for something to say to fill it, name it with a twist:
”Well. This is a perfectly normal amount of awkward.”
Or
You’re 40 minutes into a second-date hike that the trail guide described as moderate. You’re both breathing harder than you expected and you can’t see where the climb ends. You stop at a switchback to catch your breath. Instead of apologizing for picking the wrong trail, you say:
“I feel like ‘moderate’ is doing a lot of work here.”
Try this:
The next time you’re sharing an unexpected or uncomfortable experience with someone, don’t pretend it isn’t happening.
Call it out. Lightly.

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