gwyn’s guide to hyperoptimised dating, #3 (knowing thyself)

in this series: #1 (#1.5) | #2 | #3 (#3.5) | #4 | #5 (#5.5) | #6 | #7 (#7.5)

Alright, ya clowns, we are so back because I just submitted the first draft of my thesis. Good riddance! In letting it spread its wings, I, too, flew here immediately.

In this episode, we do the preparatory legwork before we jump into the battlefield.

Huh? Not dating yet? Yeah. Don’t get yourself all tangled up. Fail to prepare, and prepare to fail.

We will cover two aspects: knowing thyself and knowing thy enemy (as an extension of #1).

A necessary caveat to protect my readers’ feelings because I care for you: all of this is my own opinion. I am critical by design because because criticism is the way to improve. I fully acknowledge I may be wrong, and I might change my mind in the future. If you don’t like what you see, you don’t have to read it; set your own boundaries, or others will do it for you. But interestingly, if you experience a sting, it’s probably because you see yourself reflected herein.


oo wee (gee)!

Knowing Thyself

To know yourself and conquer the battlefield, you must be able to confidently answer two questions:

Who are you, babygirl? And what do you have to offer the market?

The Rationale

I mention figuring out what you have to offer. Now, I am all against self-objectification (I deal with enough from men daily. Stop DMing me from your damn anon alt-accounts or I will jolly well block you. This is my FINAL warning; stay in your place). But if love is a game, marriage is a market, and you are ultimately a commodity on auction. You define your own value, but you will still be subjected to market rate considerations. Nobody will pay for you if you act like you’re all that but have no concrete value.

Men (and women) can smell when you are all style and no substance. My second date told me he had met a girl who was “all talk and no show”, and his evaluation of her was “arrogant”. Ugh. I cringed internally for her. I would hate to be her; the prospect terrified me. I’m sure it’s the same for you. (That being said, what does it matter what others think of you? There’s no one to please when you play by your own rules.)

The point is that you need to be realistic and pragmatic about what you really are. Again, reducing ourselves to objects in the style of Carousell — bless that hellhole — you need to set accurate prices to find buyers. If you want to reach a class of buyers (the “elites”) that can pay a lot and are willing to, you have to be worth a lot in the first place.

And it’s not that hard to align yourself when you see things as they are. Think of it this way: when you underprice something on Carousell (as I did once), the messages come in a tsunami. When you overprice it, that item sits in your storeroom for years. Only when you find the sweet spot can you start pruning the buyers genuinely interested in making a transaction. On a dating app like Hinge, the logic is similar. If you present yourself authentically, you won’t have a shortage of likes from people who are interested in you as you are. But if you’re inauthentic or booooooring, you won’t be attracting “elite” buyers — which I assume is what you are seeking.

the bar gets lower everyday

Note the emphasis on as you are. Many buyers are out there, some of which are “elites”, but that does not mean they are a good fit for you. Sure, we got a snazzy, tall, handsome, rich man out here for drinks (story below, keep reading), but he looks at you condescendingly and only wants to sleep with you. Are you going to accept that? It’s you we’re talking about, you know. You’re so much more than an item on sale. Respect yourself.

The Process of Becoming

You must first know what you are and be willing to do the shadow work to get there. The fundamental question is: do you see and accept yourself as you are?

The easy questions

  • What are your goals and dreams? Where do you want to be in a year, in five years’ time?
  • What are your hobbies?
  • What are your strengths?

And so on. These are simple questions to answer but are nonetheless crucial because where you want to go will determine what kind of partner you’re looking for. In other words, they help you piece together your key considerations and dealbreakers.

Here’s mine after I did some self-analysis. It’s not the full version because why would I reveal myself so fully to the public (yes, I am being sarcastic). I’m just putting it here because I wrote it in jest, but it works well enough.

If he does the following, I would die for him
(inclusion criteria)
If he DOESN’T do the following, he can go away x (exclusion criteria/dealbreakers)
Read REAL books regularly (yes I am gatekeeping)Read my blog and tell me how much he loves my art
Actively listen (stop using your damn phone)Act BE obsessed with me 24/7/365
Communicate his thoughts and needs (a defining feature of a secure man)Plaster pictures of me all over his phone and social media profiles
Practice ACCOUNTABILITYText me first, politely, stating his intentions clearly
Have big dick energyLike me for more than just my hot N sexy body
Hmm. It’s quite close to what I actually want.

But life’s not all flowers and sunshine.

The harder questions (the real shadow work)

What are the flaws that define you? More importantly, are you okay with them?

A fantastic example from yours truly: my emotional intensity (often confused with “volatility“, which I will never stop yapping about). Tl;dr I feel emotions to an extreme degree, ostensibly more so than others experiencing those same emotions. Let’s say the same nice thing happened to us today, and we are both happy about it. While you might experience it as a 7/10 in intensity, I’m probably a 9/10. It doesn’t seem like an issue (ignoring my hypomanic antics) until I have negative emotions like sadness and anger. When I’m sad, I’m really sad, like 9/10 all the time. And when I’m mad — haha. Like they say, hell hath no fury like a woman scorned.

  • I don’t want to get into this further because it’s irrelevant to the discussion, but to put it simply and for my own closure, I don’t believe I’m more intense than the average person. I think people have this mistaken impression because (1) I can articulate my emotions clearly through writing, and (2) most people are not as keen on expressing their thoughts as publicly as I do. But just because you don’t see someone’s emotions doesn’t mean they’re not feeling it.
  • And because I feel this strange need to defend myself again, I no longer vent my negative emotions on people. I put them in places for me. And if my friends need distance from my evil space, they are always welcome to step away from the room. It’s not their problem unless they care.
  • Finally, consider this: what is a flaw, socially speaking? In contexts like social interaction with infinite possibilities, virtually any personality trait could be perceived as a strength as much as a flaw. I discuss it as a personality flaw in finding a husband because it repeatedly emerged as a dealbreaker for prospective men. But I doubt it is a flaw otherwise. If you took this part of me away, I would be an empty husk; I would no longer be the Gwyneth adored by my family, friends, and fans.

But that’s enough digression. Suffice it to say that I have accepted my emotional intensity as essential to my identity or how I view myself as a separate individual (yay, social psych!). Once I came to terms with myself, I could easily identify and eliminate those who would not help me grow. It is OK if they do not accept me; I am whole as I am. I will find someone who will accept me and walk by my side.

And that’s the beauty of it all, I guess: when you accept your flaws, they are no longer flaws.

The Consequences of Becoming

Okay, story time. I posted Instagram stories about this immediately after it happened (see highlights > Unhinged), but I’ll do a short recap because there are so many things to take away from it.

He was the fifth man I met since the Hinge era. We’ll call him #5. He invited me to drinks at this fancy bar. We did not text much prior to meeting. But his ELO score was so high that I threw caution to the wind (a mistake, as we will see). Essentially, this guy was maxed out on his educational attainment, job/income, height (perfect 180cm, supposedly), family background, and musical/sports skills. And he was handsome to boot. His profile was so absurd that when I saw it in my matches, I was like, babygirl’s in the big leagues, baby.

But here’s the thing: I had a gut feeling I was not enough for him. I texted my friends shortly before meeting him, quote in verbatim:

tbh he prolly just wants to sleep with me. i’m not wife material for this kind of level (i am not putting myself down. i am realistic). and i wouldn’t mind but actually i would. i not feeling it tonight

Why? We had nothing in common. Not education, definitely not income, ignore height, family background unclear. I was interested in engaging in some of his hobbies, but I was not there yet. I had not yet become what he was. In other words, there was an absence of connection.

So iconic. Anyway, I left the house knowing that I would return intact. (Note the link between connection and sex.)

Lo and behold, as God willed it, I was right on the dollar. I did not feel safe around this man and it stayed that way throughout. He wasn’t actively posing a threat to me, no, but I could feel my body unconsciously rejecting him. When he asked to hold my hand, and I put them in his, my arms literally strained to pull away. When he casually put his arm around my shoulder, I had to fight the instinctive urge to lock my body. (Another funny detail: he told me he had already had dinner. I was like… oh. Now that’s new. Talk about hyperoptimised dating; even the meal is eliminated!)

We did have a single moment when we genuinely shared a laugh, but it was not enough. He told me at the end that I was not what he was looking for. I was like, OK, taken aback, but I understand (all according to keikaku).

And… I don’t think I’ll sleep with you tonight.

When those words left my pretty mouth, he demonstrated the elite equivalent of a seizure. His eyes widened almost imperceptibly (what is this, Wattpad?), and he froze in his seat, tilting his head at me like I was some alien. I stared back at him, confused… starting to understand. He was so confident he could bag me based on his conditions alone that he had not anticipated failure.

Then we went downstairs to return to our separate homes. And we were settling our last goodbyes when he suddenly stepped forward to be closer to me. I flinched and backed away. I had to reiterate that I did not intend to sleep with him. And he looked at me in that way again, with that perplexed, distant gaze, indicating his inability to comprehend how a woman (who did not feel safe with him) could possibly not want to sleep with him. By this time, I already knew that he was not honest about his intentions insofar as he did not admit them — sealing his disqualification, sexually and emotionally.

He then got into the cab, and I was left standing there dazed as if I had emerged from a chess game.

He won the game, but I won the war, I guess.

real clown-to-clown communication moment

And yes, true to his fine upbringing, he texted me to thank me for my time with good grace afterwards. But even his text was de-rizzed, like he had deflatedly realised his place. I had excised the ego from the man. I reciprocated and then wiped the chat.

(He told me not to write about him, by the way. They all do. I don’t care.)

Apologies for the exposition. To circle back to our main point, when you know what you are and what you want, you can break any man’s ego. Sorry, I mean, you’ll be able to find the one for you way more efficiently.


Knowing Thy Enemy

Speaking of finding the one for you —

What do you want, babygirl?

You need to date to know what you want. If you don’t know what’s out there, you don’t know what’s good for you. It really is that simple. If you think you know what you want without having dated anyone, you’re probably relying on societal assumptions to define what you want. If that works for you, go ahead, but your chances of suboptimal outcomes are higher.

But there’s a hidden rule here — you attract what you are.

A man from my past reached out to me on Hinge. I was amused, so I replied, but he was never in the running. Not because of our history but because he couldn’t even figure out what he wanted from a relationship (as his profile indicated, not my assumption). OK, so you want to fuck me? Then say it like you mean it, and I’ll decide. (I had decided in advance: no.)

If you are confused, you will attract a confused person. In my humble opinion, that is a colossal waste of time because I am looking for a HUSBAND. However, I’m all for it if you guys can align on your confusion and collaborate to work it out together.

And that’s the kicker: even if you don’t know, you have to know that you don’t know.

Hence, we come full circle to knowing thyself.

Marrying (haha) the Two

To me, love is about finding the ideal partner while being the ideal partner. Thus, as I reiterate, work on yourself before you get out there. A relationship is a project, and you need to pull your weight. Any self-respecting person would expect their teammates to do their part, so why should you be exempt? You might have gotten away with it in your studies, but do you think the dating circle will be this forgiving? If you want to love, be ready to give yourself completely.

Knowing yourself and knowing your enemy are concepts that kind of reciprocally influence each other, but the first is paramount.

When you know and accept yourself, everything else will come naturally.


in this series: #1 (#1.5) | #2 | #3 (#3.5) | #4 | #5 (#5.5) | #6 | #7 (#7.5)