I’m A Dating Coach & This Is What Everyone Gets Wrong About Flirting

Back in 2015-ish (What is time anymore?), I attempted to ask someone out on the subway. Not realizing their headphones were in, I commented on what they were reading, only to have the man sitting next to him—not the man I was hoping to entice—recognize my failed attempt to flirt, and smirk. I exited the train shortly thereafter.

A few months later, I was meeting a friend in the West Village for dinner. They were running a few minutes behind, so I decided to grab a glass of Sancerre at the bar while I waited. Finding the bartender awfully dapper, I attempted to make conversation. Truth be told, I can’t recall my exact language, likely a blocked memory from the embarrassment that ensued. But I do know I made some backhanded attempt to express that I found him attractive by commenting on how many women must hit on him. He swiftly informed me he wasn’t interested in women. Men were more his vibe. I buried my head in my hands.

Happens all the time! He shot back.

Doubtful, I thought. He ended up comping my $17 glass of wine because he felt so sorry for me.

A few weeks ago, my editor at mindbodygreen reached out about an article related to flirting. She was curious to get my thoughts on it as it related to new ways of flirting as we slowly rise from the pandemic. It got me thinking about the act in general. Was it learned or inherent? Could someone become better at flirting by way of words or content? 

Clearly, by way of the previous anecdotes, there was a significant spell in my life when my attempts at flirting were misdirected and subsequently ineffective. But did that have to do explicitly with my skill, or lack thereof, at flirting?

I recall the first time my attempt to flirt with someone went well. Really well. After a farmers market run, I’d dropped into my favorite neighborhood coffee shop to grab a latte and read my book. I immediately noticed the man sitting opposite me on the other end of the communal table. He, too, was engrossed in a book. 

I figured it was an innocuous enough comment to ask what he was reading. If he was coupled, he could answer and move on with his day. Similarly so if he was interested in men or uninterested in me for some other reason. Within minutes, though, we’d made our way through small talk, and he asked for my number. 

I’m Alan, he said, sticking out his hand.

Clara, I said, extending mine toward his.

I have to get going, but want to grab dinner sometime? he asked.

That’d be great, I said.

The book comment worked, but that wasn’t the element that led to such fluidity. The morning I met Alan wasn’t a typical weekend morning. It was the first one in months where I’d started to feel any semblance of normalcy. 

Five months prior, I’d been diagnosed with a severe case of SIBO and leaky gut, one that left me relegated to doing little but work, sleep, knock back 25-plus herbal antibiotics and supplements per day, and subsist largely on poached poultry and rice.

Aside from one weekend trip to visit a friend, during which I napped for several hours daily, I didn’t do anything. I couldn’t do anything. My gut issues were a byproduct of other, more foundational, issues—mismanaged anxiety, a decade-long eating disorder, insurmountable work stress—that I’d been ignoring for years. Coffee, Lexapro, and longer hours spent working could no longer numb those realities. 

So, as our bodies tend to do, mine took the situation into its own literal and proverbial hands. It was as if the holes that perforated the lining of my small intestine were screaming: Wake the f*ck up. You’re not listening. You’re not listening to your body. You’re not listening to your inherent needs and wants.

Now I had no other choice.

The morning I met Alan fell within a newfound season of ease and physical embodiment.

It’s a common tale. Underlying stresses get ignored for an extended period of time. A physical ailment, much like a wave, starts to build and build and build. And then it crashes, disrupting everything in its wake. We’re forced to get elemental. We’re brought back to the body. To what we’re ingesting, literally and figuratively. We’re forced to prioritize like never before because there is so little bandwidth to work with.

Healing my gut was an act of coming home to my body. Something I’d never really called home. Rebuilding the walls of my small intestine became an act of discovering what it actually meant to hold my body in such reverence.

The morning I met Alan fell within a newfound season of ease and physical embodiment. The weather was still warm enough to get away with a tank top and shorts. My hair sat in a messy pile on my head, a few strands haphazardly framing my face. Not a swipe of makeup to be found, I was completely in my element. A bag splayed at my feet holding bunches of Swiss chard and crusty sourdough. My journal stood open, the pages noticeably filled with black ink.

I wasn’t sure I even wanted to know Alan when I inquired about his reading material. I more so wanted to play with this fresh fluidity. This ability to act without attachment, given this newfound safety in my body.

We’re inherently drawn to people who are at ease with themselves.

We’ve all experienced forced flirting. The slightly (or not so slightly) inebriated finance bro that sidles up next to us at the bar, offering on-the-nose compliments, a little too forcibly showing all his cards. It feels as if he’s reading a script, using a “formula” to push through his insecurities. But in doing so, he loses all credibility—and draw for that matter.

In that way, it’s the very act of attempting to “flirt better” or “be more flirty” that not only doesn’t work but pulls us completely out of our bodies. It makes us more rigid and uncomfortable as we attempt to enact something that doesn’t feel innate to us.

We’re inherently drawn to people who are at ease with themselves. This goes well beyond the bounds of romantic scenarios. Consider a colleague you admire or a friend you find so enjoyable to be around. A yoga teacher whose class you never miss or a server who always makes you laugh. They’re likely all at ease with themselves, which puts you more at ease.

Instead of contemplating how to become better at flirting or be more flirty, consider how at home (or not) you feel in yourself. Do you hold shame or discomfort around your body or job? Financial status or height? State of your home or the handbag you carry?

I’m not implying that flirting well or comfort in ourselves equates to zero insecurities. But the greater the frequency and magnitude of our insecurities, the more they sit at the front of our minds, the more clunky we’ll find it moving through any social situation. Romantic ones, especially.

The ability to flirt and date with ease doesn’t rest on the right pickup line, which I know you already know. It rests on you. On your ability to navigate the messy ebbs and flows of your own humanity, with the wherewithal to own your desires in the process. Especially the ones that are as seemingly simple as, I like you.