A Girl Walks Up to a Guy in a Club...

Find out why, and what she (*ahem* I) said in today's mini Overthinking It.

Currently overthinking…

…whether to share this “mini” essay on Threads, Substack Notes, as a paid post or a bonus public one…

Newsflash: I’m experimenting with (almost) all of the above. You’re welcome, and back to regularly scheduled programming next week! :)

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Sneaking in a selfie inside the mirrored bathroom at The Stranger in NYC.

I am not a good flirt. Genuinely have zero game. I can maybe give some eyes or a smile, but beyond that, I’m useless IRL. So when there were some clear vibes between me and a guy at a club last weekend, the overthinking began:

“But what do I say?”

“It’s so loud in here. Will he even hear me?”

“Am I sure he’s not looking at someone else?”

I’d gone out dancing with a friend in the city, which is not a thing I’ve uttered much since, I don’t know, 2006. I kept ending up around this one handsome man who seemed to be there with friends, but also doing his own thing and regularly inching closer towards me. My friend confirmed he was checking me out, which also feels like a thing I haven’t uttered since 2006.

By 10:30 p.m., it was now or never since he was saying his goodbyes to his friends. (This was “Matinee Social Club,” an event targeted to millennials and Gen X-ers who want to be home early enough to binge before bed. Evenings start at 5 or 6 and end at 10 or 11.) So I did what any still-single 46-year-old slightly high on a gummy and certainly full of DGAFs would do: I intercepted him en route.

“Are you leaving?”I ask.

“Yes,” he goes, “why?”

And I go: “Cause we didn’t even get to say hi first.”

(Note: I feel like this is coming across way smoother than it was or felt. But fuck it, let’s go with it!)

Then he offers me his hand and goes, “Hi, what’s your name?”

I told him, while shaking his hand, and asked him his.

“Dan,” he said. “But… I do have to get home to my wife.”

…

The moral of this story isn’t the disappointment I felt for the rejection, and the embarrassment for forgetting to even look at his hand to check for a ring earlier than his offering it to me for a consolation shake. It’s also not that overthinking takes its toll when it doesn’t have to.

But rather, yes, Glennon Doyle, we can do hard things! And this felt like a hard thing! Especially for a non-flirt like me. But I couldn’t have left without knowing. I’ve done too much of that before, and it’s gotten me nowhere.

It got me nowhere for nearly a decade-plus, actually, with my first love and ex-boyfriend from high school, whom I pined for post-H.S., post-college, and even during our 20s and early 30s in NYC, where we continued to roll in the same circles. Maybe one day I’ll share that story, but basically, I was convinced we were destined to be together. Until one day, after one too many almost-but-not-quite-confessions during nights on the town together, talking about our life goals and how he was going to illustrate my cover stories for New York magazine, I also put my feelings out there. Sadly, they were unrequited, but fuck it felt good to at least take what I sensed in my head and my heart and try to find a home for where I thought it belonged.

Back to Married Guy and last weekend. Just those couple of hours of us seemingly dancing around each other felt interminable, and yet finally going for it took less than a minute and maybe a dollop of pride. By putting it out there, I now had an answer and could move on. It only stung for a few seconds, and at least he was on the way out the door. I didn’t have to face him amongst the strobe lights, nor did I run into him in the lobby some 15 minutes later when we left, only to be grounded by a sudden spring downpour.

The worst was over, and instead I could relish in not only the giddiness of the “before” and the aura of the flirt, but the act itself with my friend, who pumped me up with praise and compliments for my courage. What’s more, the high (natural now, to be sure) continued the next day during spin class when the instructor played “Jumpin’ Jumpin’” by Destiny’s Child. I couldn’t help but smile to myself while singing:

“Ladies leave your man at home

The club is full of ballers and their pockets full grown…”

My pockets are definitely not full-grown, but my head and my heart are, and that club was indeed full of ballers — myself among them.