That Time I Tried To Be A Pickup Artist

Banana with lipstick stains all over it

Photo: Deon Black

“Hey, any idea what’s cool to do around here?”

The woman I’d just spoken to held her book closer to her chest, sidestepping away like a crab. No reply, no smile. In fact, she scrunched her face as if I smelled like goat droppings.

I still cringe at the memory of me talking up to random girls in the shopping mall, just because I’d gotten a copy of The Game during my young adulthood, and I thought it that it would be the key to my relationship problems.

Spoiler alert: it wasn’t.

To the uninitiated, The Game was a book written by Neil Strauss about his venture into the pickup community. And if you haven’t heard that term before, then let me basically say that it is to men what self-help gurus are to the unmotivated—a promise, a way out, hope.

Of course, if you’ve ever been involved in either of those, you’d probably know how creepy things can get. As someone who’s dabbled in both, I can say that I’ve had my fair share of Kool-Aid experiences.

But hey, every bad experience makes for a good story, and while I came out of both phases having learned nothing about what I actually wanted, I did at least learn some things about life itself.

It probably makes for a good blog post this week too, so break out your comfort drink, kick back, and enjoy the time I’d like to call my failed pickup artist phase.

You can’t fake real

Real recognises real, and sadly, real recognises fake as well. In my quest to become the smoothest stranger ever, I actually found myself wanting when it came to the ‘normal interaction with strangers’ department.

My disingenuousness was evident the time I tried dressing up to look cooler than I actually was, and it also reeked through my pores when I blurted my openers, as suggested by internet strangers.

“Do you floss before or after you brush your teeth?”

“Nice nails. Are they real?”

“Hey, I need a quick opinion on this debate I have with a friend…”

I know, I know, they sound stupid on paper. Let me assure you that it was that much worse once I delivered them. Drunk. In a club. Yelling over loud music.

You see, socialising is like a game of tennis. You serve the ball, then I play the return. We go back and forth, and if no one drops the ball, we have fun. But if someone who has no clue how tennis works steps into the court just because they’d heard it was one of the ways to get to Wimbledon, then everybody’s going to have a bad time.

I was that guy. I had zero idea how to play this metaphorical tennis. I wanted the prestige that came with playing such a fancy metaphorical sport, and I wanted to look cool in the process. But acting like I belonged was a tall order, especially when I didn’t know my way around the metaphorical racket.

Yeah, this is where I learned that I shouldn’t have been working on my pick-up lines. I should’ve been working on my life instead.

Many ways to skin a cat

And there were also many ways I could’ve met women. I could’ve, for instance, actually did something interesting. Things like rock climbing, martial arts, dancing—all which I’ve done later in life—could’ve been a great way to get better at something while making new friends.

They definitely would’ve been better alternatives than yelling my name in crowded clubs, drenched to the pits with sweat, and thinking that that made for an attractive introduction.

And you know what? This is where I learned that there’s no one way to approach life.

You don’t need to pursue a diploma just because you want a job. You don’t need to be ruthless to climb the corporate ladder. Heck, if my career is anything to go by, you don’t even need working experience to land your dream job.

Oftentimes we take these gurus’ word as gospel, and we think that there’s only one path towards our goals, but I’ve since realised that life isn’t that binary.

Man doing 'dolla dolla bills' make it rain gesture

Just sign up for my course and I’ll teach you how to make money from your bedroom. Source: GIPHY

Listen to your consience

Don’t change unless it’s for yourself. A hackneyed phrase, that one. Yet it’s only after I’d tried changing myself for the world that I began to see just how true it was.

I never enjoyed the party life, I hated spending entire nights sucking at metaphorical tennis, and I didn’t enjoy spending money that I didn’t have.

But I kept buying new clothes, paid for bottle entries, and even feigned disinterest when I actually longed to see a girl again. All I got for my efforts was the reminder of how fake I could be.

You know what type of relationships you get when you base them off lies and pretence? Ones that crumble the moment your partner finds out who you really are. And it gets much worse when you fly off to another country to live with them before that happens.

And I was an insecure good-for-nothing whose main goal in life was just to look cool for the ladies.

One day you’ll find the one

You know what’s the best thing that’s ever happened to me during my pickup artist phase? I stayed single for a long time. As sad as that sounds, it’s actually one of the best things that’s ever happened to me.

Because like a monk that’d let go of their attachments, I too began forgoing the idea of being in a relationship. They say that from stillness comes clarity. And by my love life being as still as a century-old pine tree, I began to uncover who I really was on the inside.

I believe that life happens for me, so maybe the events of my life had to play out the way it did in order for me to meet Len. Because had I met her at any other point in my life, I probably wouldn’t have seen all the traits I look for in a partner.

Also, had I still been in pickup mode, I probably would’ve scared her away with my prowess of being a douchebag.

Be yourself, but better

In the end, when we find the right person, we won’t feel the need to change. The right person would encourage us to stay true to ourselves, yet they’d inspire us to be the best we could be.

That doesn’t mean that it’s easy. Relationships take work. But it feels right, and that’s the most important thing.

I guess what this all boils down to is that—cliche or not—you have to first work on yourself before you can share your life with someone else.

Awesome! Do check your spam folder too, just in case.

45 thoughts on “That Time I Tried To Be A Pickup Artist

  1. Playing someone you are not never works. Sooner or later people see fakenes of your actions and/or look and start avoiding you. The best you can do is to be yourself and find people that appreciate you for what you really are. I’ve seen a quote that sums it up perfectly: “Be yourself, everyone is already taken” !

  2. I relate to this in a way. No I have never used pick up lines and I heave learned from you not to.😅
    But I suck a socializing. Really suck. It’s cool to find someone who’s done it worse😅😁
    Amazing post!

    • Heh heh, fellow socially-awkward people, high five! Weirdly enough, the more I’ve embraced that side of me, the less awkward I’ve become. It’s like a Catch-22 thing. Anyway, thanks so much for stopping by!

      • Actually, that’s true. If you kinda get comfortable with it, it becomes less obvious. Or maybe it doesn’t. I dunno, I’ve never asked anyone, “hey how socially awkward am I now?”
        Anyway, sure, anytime.😊

  3. spot on, Stuart ; you can’t fake real — and get away with it ; the same , I suppose, applies to our posts: the good ones come across as authentic, even when a little clumsy —

  4. Snazzy newsletter widget thing, Stuart! Subscribed right away. I won’t be surprised if you’ll be able to make some good coin from this blog a few years down the lane. Keep running on the right track, and if you fall off the wagon, get up on it again before it disappears.
    This was a good post to wake up to. Loved it! But mostly I was excited because ~stuart has a frickin’ newsletter now that isn’t as cheap as the regular WordPress follower thing~
    Now, writer’s question for the week: Would you rather wear nerdy triangular glasses for the rest of your life or write AND EDIT a 40,000-word draft in a month? Let me know!

    • Wow, your comments are always amazing, Emily, and it’s an awesome one to read right before I wind down for the night.

      Thanks so much for signing up for the newsletter! Really appreciate your support.

      In reply to your question, I probably can’t pull off triangular glasses, having a square head and all, so I’ll opt for option number two and just edit as I go :P.

    • Definitely! Sometimes I think that doing these lame techniques are what’s going to teach you that they don’t work in the first place, so there can be good from that. Thanks for stopping by!

  5. I think it’s a sign of an emotionally intelligent person to be uncomfortable when you’re trying to be someone you’re not. It’s your psyche’s way of warning you to turn away from the wrong path because it will only bring unhappiness. The discomfort is a built-in warning system. And who wants to be with someone who doesn’t love you for YOU? Like imagine being one of those people who make sure their spouse never sees them without makeup.

    • ‘Like imagine being one of those people who make sure their spouse never sees them without makeup.’

      Funny you should mention that, because I’ve been with someone who was like this too! As in, she’d NEVER let her hair down in my presence (figuratively). It was taxing to always feel like a stranger.

      Anyway, thanks so much for your thought comment as usual, Hetty!

  6. Another nice candid post Stuart, I can related to being there in parts and realising how horrible a fake tuning of our personality is. It attunes us to imitate a horrible standard and in essence bringing down the quality of our life and personality to a lesser sense. Instead, focusing on just the reality and honesty is a powerful goal. If we look closely, most things or influencers around us are marketing activities. It is nothing to do with reality and understanding our personalities which can easily provide brilliant outcomes.

    • Oh yeah. Lately I’ve been thinking about the quote ‘If a man is right, his world will be right’.

      I want to get myself right first. I don’t want to use ‘techniques’ or ‘hacks’. Getting there is the hard part though.

      Anyway, thanks so much for your thoughtful comment!

  7. What a delightful post! Thanks man…I can always count on you to put a smile on my face. And yes, totally with you on that parting point — first work on self, then the rest, as they say, will follow! You got this!!

    • Oh yeah, you have to put on your own oxygen mask first before helping others with theirs, yeah? It’s a continuous journey though, and I do hope I get myself to where I need to be. Anyway, thanks for this post!

  8. Wow… After passing this phase continuously in my life,I came to the conclusion that I’m an antisocial genius. Genius because I found out that I couldn’t interact with people when I haven’t with myself. I’m surrounded with people who are way more different than I am so how on earth do I relate with them?

    Amma just sit back,away from being a “socialist”everyone’s bestie and focus on myself and what I love so I can give back love.

    Thanks for this Stuart. Its never a waste of time reading your blog post.

    • I love your observations. It’s the perfect demonstration of ‘light the fire within yourself before you seek out to do the same for others’.

      What a lovely comment to wake up to. I really appreciate your words!

  9. I’ve never tried the pick up artist thing, mostly because I’ve been told I look like a serial killer and I make people nervous, but I will say that whenever I try the flirting thing there are always three outcomes:
    1) They are taken.
    2) They are lesbian.
    3) They are younger than I thought.
    However, there was one time where a nice lady old enough to be my grandma told me I had a voice for radio, so that was nice. But I’m pretty sure I am cursed.

    • Hahahaha well humour always works, and if I was a girl I’d tell you you were a funny guy. And not in a bad way too. Unless of course you suck at flirting. Then I’ll probably tell you I’m taken.

      • I just talk to them, but apparently my voice changes to a more Southern gentleman drawl when I do. I never noticed this, but a few people have pointed it out. I don’t know. Social interactions is hard. Much easier to speak behind a cartoon horse in clown makeup.

    • Lol sometimes our bad experiences in life make for great stories, and as writers, that’s our silver lining for when we go through cringe moments. Thanks so much for your lovely comment!

  10. hahaha really enjoyed this post! I kept creating images in my head with all these you describe :)
    Pretending to be something you are not will only attract people who like you for beng someone else. In long term this can be exhausting. I think it is better to know that somebody dislikes you for what you truly are than somebody who likes you for something you are not.
    Loved reading it! thank you <3

    • ‘I think it is better to know that somebody dislikes you for what you truly are than somebody who likes you for something you are not.’

      Wow that sentence blew my mind. It explains why it feels so bad trying to be someone you’re not. Thanks so much for stopping by! I appreciate it!

  11. What an interesting piece, I’ve heard of the book and knew some of the negativity it’s followers ran with but I don’t think I’ve ever heard anyone say hey I tried this. I’m glad you learned what you needed to, I think time alone is so valuable to learn about ourselves and what we actually want and what we can do for ourselves.

    • Oh yeah, I had the crappy love life during my young adulthood to spur me into trying anything. I’m glad you enjoyed the story, and that you took the time to drop this wonderful comment too, so thank you!

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