Dating: Are You Up For A Challenge?

Famous Steve
6 min readDec 16, 2021

Society would tell you I’m bad with women. My questions make the smart ones feel dumb, and the dumb ones I don’t talk to. Instead of being sexy, I delve into their soul, preferring to know the real them not the mask they hide behind. With my track record, believe me when I say sexy is better. She wants you to go deep, and she doesn’t mean the conversation. I want to go deep too, after a deep conversation. Why wait a year to find out something I can snip out in two weeks?

People won’t like you if you can see through them. Majority despise therapeutic questions on romantic dates. And the ones I do hit it off with, I find reasons to run. This happened, that happened, I don’t know, and before I come to, it’s been a week and I still haven’t responded to “How are you?”. By the time I respond, that is, if I respond, she’s moved on. Marked me unreliable and just like that, that story ends.

What happens to a man who meets women but fail to connect with them? He keeps meeting women. Nothing really happens. You enjoy what you can. Conversation here, dates there, one night stands, whatever comes. You enjoy and move on, believing the next one would stay awhile.

They say look to yourself and you’ll see why you’re single. I have looked, I have seen and I made a deal with myself that I would not change. My questions remain, I’m not putting on a mask, I remain Me — improving here and there of course but not because of a girl or some external factor. And the only way to know who’s right for me is for her to enjoy knowing Me. well, “aint nobody got time for that”, so I don’t wait around for a partner in crime, I instead continue to enjoy life as much as is available to me.

They say when people don’t have problems, they invent one. Well, I like inventing.

I am however feeling ballsy in this moment, the workout juice is still pumping through my veins and I would like to enjoy this journey, well record this journey so I can remember this journey. Thing of it is, I would not be single forever, if I can just see people as humans and reduce the perfection list, maybe I can make a human connection, or not. Anyway, before I attach wedding cans on a getaway car, I want to make it fun.

I am challenging myself, in this moment, to record (that is, write down) all the girls I encounter, interactions that could have led to something if “stars” were properly aligned. This does not include the working flirty waitresses (unless they go out of their way to make it painfully obvious) or the “unintentional” boob rob on your back from the Soccer mom standing close to you, who’s bored to tears with her “better half”. This would be girls I actually conversed with and might have dated but xyz happened. Fill in the blank.

I want to write down 100 interactions, on paper. Her name, city, where we met, date. That’s it. Nothing major, I could add the last text message or sentence said or that would make it a homework and I left school a long time ago. Something simple, I could add ethnicity, if I can decipher it but really basic information. It’d take years but how else to start a New Year all pumped and excited than to walk around with paper napkins in your back pocket.

Here’s the head scratching part, what if I fall into a relationship before I pass 10 interactions? Well that would suck. Not for the girl, it’d be exciting to be in a beneficial relationship but terrible timing for the challenge. Anyways, challenge would be stopped. Other than that, let the note taking begin. This makes me think of the movie “Love Guaranteed”, exciting! To clarify, I’m not going to intentionally ruin the interaction, I am going to be engaged and ready — knowing my dating style doesn’t mesh well with women on this side of the sun, and humans aren’t perfect, it would come to its natural end soon enough. And, I’m alright with that.

Hi, what your name is, where are you from?, what’s today’s date? Awesome, thanks. Call me sometime.

I’m not trying to be “right” at dating or good or whatever the proper adjective is, I’m just trying to enjoy the process. Be present where I am in life. And, enjoy it. Do you agree?

Whenever I’m honestly ready to “settle down” I can, in less than six months, be boo’d up, singing Usher and Alicia Keys — but first let’s give my Disney brain washing a chance, like the young ones say — “let’s give love a chance”.

Some would say:
“Is this all a game to you?, I can’t believe men sometimes, playing games with people’s emotions. Who do you think you are? She got dressed up, took her forever time to come see you and you just move on like she didnt matter. Well she matters. You are the problem. You should fix whatever boredom you’re going through and not waste people’s time.”

Alright, thank you. Your opinion has been duly noted. I will keep you updated on the progress.

I have a girl already, actually, to write down. I just invited her out, she said she can’t do today — well, I don’t know if she’ll ever hear from me again — nooooot because she’s horrible but because she did not suggest a different day, and I don’t feel like reaching back out anytime in the future to ask her out again — see I’m not completely hopeless, I do try. Such a downer, I really should be more optimistic, anyways 99 to go.

I am excited for a challenge, are you?

The funny part is, if you take it less seriously, you might actually meet someone incredibly attracted to your nonchalance. And my brain can take a break from contemplating why it did not work out or how to kick her out, without kicking her out.

Things, hopefully would go the way they were meant to go, come to their natural end, either by my works or her words, but either way at one point in our lives, we shared a moment together, no matter how insignificant or life changing it turns out to be. Now, what I would do if I go through a hundred girls without picking one, well. . the always wise, good Bible has a generous answer: “Therefore do not worry about tomorrow, for tomorrow will worry about itself. Each day has enough trouble of its own.”

Now, that’s how you dodge a question!

I’ll stop here, the post workout juice has depleted.

Let the adventure begin. Vamos!

With Love,

Famous Steve.

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