Always Go For The Number

A little reminder of all the things that could have been

Jonathan Adrian, MD
3 min readDec 23, 2019
Photo by Tim Foster

Imagine this.

You’re perched on a bench, enjoying the scenic view in front of you, and the cup of hot latte that’s clutched onto your hand — still pleasantly warm to the touch. You took a little sip and rejoiced in the tranquility of the current moment.

As your eyes panned across the scene, you caught a glimpse of a woman sitting on the far end of the same bench you’re sitting on. You noticed that she was alone (and strikingly alluring), and you start stealing glances at her. You became curious.

You observed that she too was holding a cup — presumably coffee — deeply entrenched within her own thoughts, her gaze seemingly fixed into the fascinating bridge that spanned across the landscape.

Then began the mental excursion. You start weighing up on whether or not you should approach her.

Is she waiting for someone? Is she trying to find some alone time?

After what feels like an hour-long minute, you got up and decided to make your move.

You opened with a thoughtful remark of the scenic grandeur that laid ahead and instituted the prospect of a conversation.

She inclined. You transitioned into a topic about the weather, then about Donald Trump’s impeachment, and then traversed into a lively discussion about intermittent fasting — which you just attempted last week and failed tragically — and Greta Thunberg’s recent naming as Time Magazine’s Person of The Year.

Then 10 minutes went by.

Then 20.

Then she had to leave.

And then the thoughts start racing through your mind. And you start formulating a mental debate with your inner sceptic.

Do I ask for her number? Did she find me annoying? Did she like me? What if she rejects me? She’ll probably just flake on me later.

Eventually you ended up reasoning with your frontal cortex. You resorted to rationale. You gave in to paranoia. Your brain won and your inner courage lost.

Then you bid your farewell, proffered a hug, and then she walked away, and you never saw her again.

You’re shattered. You start thinking about all the things that could have been. You enjoyed that short conversation. You would have loved it if it turned into a first date… or a second… or a third.

Scenarios like these don’t only occur in my mind. They happen to me on a consistent basis. I’d come up to a girl, and we’d have this genuinely amiable conversation, seasoned on my part with some clever confidence and a bit of witty cockiness. But then I’d curl up into a ball when it came to asking for her number.

All that’s left in my mind are the thousand worst-case scenarios that could have ensued. It’s not just the fear of rejection that’s involved, it’s the fear of having annoyed someone and ruining their day, the fear of appearing like a skirt-chaser, and the fear of self-humiliation. It’s an endless list of pessimistic what-ifs.

But they’re all just made up scenarios, rendered by the paranoid nature of your cerebral cortex. The prospective gains from this relationship are frequently overlapped by your sense of fear. Your false belief of what should’ve been, masking the possibilities of what would’ve been.

In truth, nobody can really say what would happen if you went and asked for their number. What would my life look like if I were to ask and follow up on all the women that I had encountered. On the extreme, a wife perhaps, but there’s no way I would have known unless I actually dove in and asked.

It’s like a premature divorce — one that occurred before you even went on your first date. The prospect of not having asked sounds scarier when it’s framed this way.

It’s only by asking that you can stop asking yourself the what ifs, and actually start living your life questioning the what nexts.

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Jonathan Adrian, MD

Doctor, writer, photographer, and part-time social media strategist.