Sometimes you have to roll a D20

I would not describe myself as a confident person. Over the past seven years I have grown out of my shell, shed the nervousness, the shyness, but I wouldn’t say I have an abundance of confidence. Still I am capable of moments of shyness, moments where I want to throw my hood up and hide from the worlds around me. But to outside observers, I appear to be possessed of some compelling form of confidence. Though I would personally define it as a kind of foolhardy madness, it gives some appearance of confidence. Allegedly.

Today I leave it to you, dear readers, to judge whether it is confidence or madness. I have been inspired to write this by two things: 1) Recent actions that have been defined as confidence and 2) A friend’s Facebook post.

As many of my single compatriots are acutely aware, the Socially Appointed Day of Obligatory Romantic Appreciation of Partners and of Singlehood Awareness approaches. Or in the common vernacular, Valentine’s Day. Closer to the day, I wish to delve into the concept a little more, so I’m going to gloss over my own Valentine’s Day context for now. Right this moment I am going to jump over point one to point two. It makes sense in terms of narrative flow, trust me.

I witnessed a Facebook post by my friend Mako, highlighting that a lot of her friends are bemoaning the approach of Valentine’s Day. Railing against the social custom because of how much it emphasises that they’re single. Mako then makes an interesting point. Even though it has become an inherently commercialised “Hallmark holiday” as she puts it, it is also a day for single people to seize the moment. A day where they can shed the usual cares and worries of social protocol as this day has been Socially Appointed as a day where not only couples show affection, but singletons can express theirs to those they wish to shower with affection. As Mako says “seize a moment without fear; and get a cheesy card while you’re at it”.

This abstractly brings me to the events of Sunday, February 1st, 2015. Thirteen days before the appointed moment, I nonetheless, for all intents and appearances, decided to seize it anyway.

Okay, I’ve talked about my train wreck of a love life in some abstract terms before and there’s a part of my brain wigging out a little that I’m about to post this, because it’s revealing a genuine moment in my life. And, by extension, a moment in someone else’s life. So a lot of details are going to be very deliberately obscured.

On Sunday, I encountered a girl I have previously met. Someone that I have chatted to on occasion, someone I have found very attractive since the moment I first met her, but I don’t know very well. And on this particular Day of the Sun, I decided that I should seize the opportunity, the moment, as we do not oft cross paths. I wanted to rectify that, as well as the part about not knowing much about her. Two key philosophies helped me to do this.

First, Shakespeare. My favourite quotation from his works – Polonius, Hamlet, Act 1, Scene 3. “This above all: to thine own self be true.” I entered into some debate with myself over whether to ask this girl out. I kept trying to talk myself out of it, reasoning that it would be madness, something so out of the blue from someone she barely knows. But I couldn’t shake the words. I couldn’t shake the sure and certain feeling that I really, really wanted to do it, otherwise I wouldn’t be trying to talk myself out of it so vehemently.

Second, a Chinese proverb. “He who asks is a fool for five minutes. He who does not ask remains a fool forever.” I would later quote this to the girl in question and she agreed with the wisdom of it. I knew that not asking her, that letting the moment pass, would make me feel even more of a fool than asking.

This story, alas, ends with me feeling a bit of a fool. For reasons I shall not detail, she declined (in a very nice, let-down-easily way) to go out for a drink with me. We parted on what I believe and hope to good terms and I very much hope to see her again.

The point I’ve been making and driving at all this time, the reason for the choice of title is, well...in the title. Sometimes you have to a take a chance. You have to roll that D20, praying for the natural twenty, the critical success that leads to bliss and happiness (or glory and riches, depends what you’re rolling for). But you can’t ever get that critical success unless you roll and take the chance. Whether you take that appointed day, February 14th, or any day before or after. Change your stars. Roll a D20.