sex – baby g’s diary

gwyn’s guide to hyperoptimised dating, #6 (heartbreaks and goodbyes)

11th Aug 202413th Sep 2024 gwynethtytLeave a comment

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

Good Night, Sleep Tight, Don’t Let the Loverboys Bite

Who’s Next on the Hitlist Tonight?

Here are some guidelines I used when deciding to sever a connection. These apply to both texting and in-person behaviour. All are inherently subjective, so make your own decisions.

Perceiving a lack of interest on their end
- Inconsistent or a lack of replies over a prolonged period without acceptable justification
  - For men I hadn’t met, I observed them over 3-5 working days before deciding. They don’t owe me anything, but I can sure decide when they didn’t like me enough.
  - For men I slept with, I gave them 24 hours before culling. The shorter time frame is because a man who likes you will demonstrate intensified interest immediately. Don’t make excuses for them like oh, but men are rational, so maybe he needs some time to think. Men do not sleep with women and become infatuated with them because they’re rational creatures; it’s precisely the lack thereof that drives them. Diminished interest means it’s over because they only wanted one thing, and you’ve given it to them.
  - One-word replies, dry texts, perceived difficulty in sustaining a convo despite attempts (it’s not worth it)
  - Not seeming interested in your day
  - If they’re only talking about themselves all the time like hello what about me
Predominantly sexual conversations to the detriment of other, far more interesting, topics
Actions that do not align with their words — especially broken promises
If they ask for anything that crosses your boundaries.
- Example: At least three men shared with me one behaviour in girls that they consider off-putting: expecting him to travel to her place to pick her up before travelling to the destination together and accompanying her home afterwards. Of course, it was expected that the poor man would pay for all expenses. I don’t agree with this either. But see the next example.
- Another thought-provoking example: beliefs about who should pay on the first date. I’m not ashamed to say that I fall into the camp that the man should pay — it’s an (admittedly gendered) way for me to suss out who values me. I acknowledge and respect that not all men agree, and this precisely works to my advantage: I had a hidden rule that if a man asked me to pay, he would be permanently DQed. No exceptions. Not that any of them asked me to go Dutch (or y’all would so know it), but the point is that specifying what you want improves search outcomes. Everyone has exclusionary criteria. Sorry if it hurts your feelings though.
- Final example for the sake of controversy: two men asked me for head via text. I played along with one and shut down the other. (FYI: neither got it.) The only difference was in how long we had known each other. It boils down to accurately assessing your partner’s boundaries at the moment and knowing how to best accommodate them (signs of EQ). This is an ongoing process as boundaries are continually negotiated as a relationship develops.

In summary: drop if they are anything less than you think you deserve (given that you know your own worth).

The Art of Saying Goodbye

In babygirl’s humble opinion, good and clean breaks have the following characteristics. They:

Are respectful of the other person. This means NO personal attacks. Even if you think they’re trash, write it in your diary (hehe) or sob to your friends, but don’t tell them.
Focus on your perception of the relationship, not the person
State simply that you have concluded the two (or more) of you are incompatible, and briefly state the reasons that led you to this conclusion
Imply that the decision is final and non-negotiable
[Optional: if you want to keep them in your life as friends, indicate so. But you MUST give them a choice to take up your offer or not].
Wishing them the best in their love quest and life

Based on the above, a sample template for saying goodbye:

hey, i don’t think we’re going to work out. we’re not aligned on some fundamental aspects (e.g. values, goals in life) / i just feel we don’t like each other enough — i’m sure you understand. but thank you for having given your time to me; i enjoyed our connection immensely.

[i really like what we have though and i still want to be friends with you. but that’s entirely up to you, and you can take as long as you need to decide.]

i really hope that you find the love you deserve, because you do deserve it.
source: the lovergirl in me. adapt to your style or whatever

All of my goodbyes with my dates went something like this and ended on a relatively positive note. There was no face-tearing, at least. In the game of love, we have no time for hard feelings.

A well-crafted goodbye will be accepted without question by a secure counterpart. It will also neutralise any player energy that the person might have had.

Please do not ghost them if you have at least bonded somewhat. That is pathetic behaviour and hurts everyone. Get them out of your mind pronto and help them do the same.

The Art of Receiving Goodbyes

You may be surprised (I’m joking), but I have been rejected too. What matters is not who has rejected who (instant gratification aside) but how you learn from the experience.

So how do we do so?

Ask for feedback if you are unsure why you were DQed. I brazenly asked “so why am I not a good fit for you?” after one of them told me I was not what he was looking for. He was surprised at my directness, but he was nice enough to share that I was too emotionally volatile for him. I did not agree, but I did not attempt to defend myself or lecture him otherwise. I accepted it, thanked him for his time, and wished him the best. I then did some intense self-reflection and refined my Hinge profile to filter out men like him. LOL
Manage your emotions. Absolutely critical. You must not enter another relationship until you have processed your thoughts and feelings with the previous one. Of course, I had a good cry sometimes when things didn’t work out with my handsome boys. And then I got over them and moved on in a few days. I think it helps to remember that none of it is personal. The both of you just happened to be incompatible; you were not what they were looking for, but that doesn’t say anything about your worth as a person. You remain valid and worthy of love.

I’m Only Gonna Break, Break Your, Break, Break Your Heart (Sorry)

Back to Basic (Instincts)

Girls have choices sexually. Men have choices romantically. It’s just stacked that way. Note the intimate connection with mate selection criteria — women are rewarded for their attractiveness, while men are rewarded for their status.

I realised I could sleep with any guy I wanted, even those out of my league marriage-wise. (OK la, small sample size, maybe the 9th man would have turned me down. We’ll never know!) Hell, I have so much power I could choose not to, and there is nothing they can do about it. Men have zero sexual bargaining power when it comes to facing off against an equally attractive woman, ceteris paribus.

Sidetrack: this is why it’s so funny to me when men slut-shame women on social media; they don’t realise it reveals more about them than the women they’re trying to bring down. Like, bro, chilé. We get it. You’re not getting laid, and you hate yourself, so you’re taking it out on women you cannot have. We know you would sleep with her if you could. But here’s the thing — you can’t. And now, because you outed yourself, everyone knows it. Get therapy instead.

But here’s the catch. I make it sound like sex is a woman’s advantage, but it really means nothing. Sexual attractiveness gets you into the bullfighting ring, but that’s all it does. The bull will kill you regardless if you don’t know what you’re doing. Even if you come prepared — you could still get shredded to pieces.

Men will not love you because you’re good in bed. In fact, the prevailing pattern I’ve observed is that men love women in spite of them not being good in bed. Legit let that SINK IN for a moment. Because men can compartmentalise love and sex, the former ironically supersedes the latter in their search for a wife. The same goes for women, although there are no surprises there.

the real enemy of humankind is the double standards we apply to ourselves, even as we impose our judgements on others without so much as batting an eye.

To all my readers: they might like you if you’re hot, but you’ll just be put in the “fuckable” compartment of their cupboard and left there. Listen and remember: if you were not pre-categorised into the “potential partner” section, you will never make it there. Put differently, the friendzone (or the fuckzone, I guess) is a finality, not a place to challenge others’ boundaries.

Do NOT regale me with tales of how Some Mediocre Man/Woman realised their errors after Some Devoted Woman/Man was consistent and always there for them (rolls eyes). Put yourself first. NO ONE IS WORTH MORE THAN YOU. We are not looking for someone who at the end of the day “settles” for you because they couldn’t find something better. Ew. You should’ve been their #1 from the start. If they are emotionally unavailable to reciprocate, that’s not your problem. You go out there and look for someone who deserves you.

Be deathly wary of people who say that they want you (back) because you’ve changed or grown as a person. First, do you only like my current version because I’m good enough for you now? So what was I before? If I change in the future into something you don’t like, are you going to drop me then? Second, if you have indeed grown, there is virtually no reason to return to your past, especially the people left there. They are there for a reason.

Inevitable exceptions to the rule: I have seen some couples who have made it out of the friendzone territory. But when I look at them, I’m not sure… I guess it’s an ego thing on my part. I could never accept being settled for. I’d think that shadow would hang over me and my view of the relationship for the rest of my life. Then again, it’s your life, your preferences, and your choice. And if you’ve reached a point where you’re secure in yourself and your partner’s love, what is there to complain about?

Back to the girls: I hate to say this — I genuinely, sincerely do — but you have to err on the side of caution. While not every man is like this, you must assume that they are only out for your body and will throw you away after they are done. If you are not ready for this possibility and discarding them in the same fashion when the time comes, do not sleep with them.

DO NOT EVER — EVER! — degrade yourself by attempting to use sex to keep a man around. If you can only remember one thing from this post this is it. I find the one “degrade” very distasteful because it’s often thrown around as a pejorative to demean women who are sexually liberated (AND SUCCESSFUL!). But when you disrespect yourself to keep someone around, you’ve completely lost the game.

All of the above also applies to emotions.

If someone does not love you fully given some time, I don’t think they ever will. I don’t believe that love grows in that sense; it can only be cultivated to persist. Unfortunately, matters of the heart are just like that. You can’t change someone’s heart no matter how many times you try — if they cannot give you their 100% despite their best efforts and yours, the two of you are doomed from the beginning.

There are no guarantees either: they could tell you they love you today and disappear tomorrow. The only thing we can do for ourselves if they waver is to leave.

You need to act like — you need to know — that you deserve the world to receive it in return. And if they can’t give it to you, the door is right there.

But you must also be ready to give your everything. You must be willing to give your time and effort to build a connection with another without expecting any return. You must be willing to hurt so much that you can only lie on the bed incapacitated, only to finally bring yourself to sit down on a chair and start sobbing like a baby.

There are limits to my guides. I can help you minimise the chances of meeting bad actors or insecure people, but that’s all I can do.

Neither you nor I can ultimately control your chances of meeting someone who will love you for who you are.

That being said, don’t forget to look around you. Your family, your friends — haven’t you seen the look in their eyes when you laugh? Even acquaintances and strangers, when you catch up after a long while, or when they stop to do you a little favour for nothing in return. Love actually is all~ around~

Time to~ Say Goodbye~

Ah, we’ve finally come to the chronological end of this series (but you never know!). What a wild ride it’s been! So much debauchery and so many epiphanies!

i unironically recommend rollercoaster by justin bieber

True to the # of this guide, I met six men from Hinge. Every one of them taught me something that I’d like to thank them for:

#1 (Gang Member) — for showing me new perspectives on love
#2 (Still Waters) — for showing me the limits of love
#3 (Sweetheart) — for showing me when love is and isn’t enough
#4 (Captain) — for showing me what love feels like
#5 (Just Guy #5, sorry) — for showing me what love isn’t
#6 (My Husband) — for showing me what it means to love and be loved completely.

Special mention for baby d and Grab Extraordinaire. It’s a pity — I mean it — but somehow I accept that it was meant to be this way. It is what it is. And Little Tiger — Nando’s soon!

I will remember the love I had for you, always, always.

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

gwyn’s guide to hyperoptimised dating, #5.5 (on players)

8th Aug 202421st Apr 2025 gwynethtytLeave a comment

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

love is not a game — and we will strike down anyone who acts as if it is
babygirl affirmations (author: me)

Supplement to guide #5, as promised. Today, we delve into the psychology of players — those pesky distractions in your Love Quest that steer you away from your path, promising great rewards only to leave you stranded with nothing.

Or so I’d say, if only things were that simple.

My observations tell me that people are tempted to reduce players to one-dimensional creatures — selfishly motivated barbarians with limited capacity for self-reflection and sophisticated emotion.

I argue that this is not true. Selfish, yes, but everything else, no. In this piece, we will strip them, layer by layer (haha), to establish my argument.

You might be thinking: OK, sis, pretty prose and all, but why extend grace to these clowns when they are out only to hurt you and waste your time?

The primary reason is that understanding them helps you to grow.

When you dissect and decipher a player’s psyche, you will see what they really are: a timid child desperate to be loved not knowing how to go about it, who inadvertently hurts others in the process.

They’re just like you, and they’re just like me.

When you come to terms with this image of them, you will sympathise with — and maybe even forgive — them for why and how they hurt you. After all, would you blame a child for causing you pain, if you knew they didn’t know better?

And only then can you let go for real — to become the person you were destined to be without them.

The secondary reason is that you can put them in their place when you understand them. I think of it as my contribution to the world. 😛

The Ivory Guards, or Two (Exceptionally Intimate) Case Studies

Prior to meeting my future husband, two men in particular were formative to my personal growth. I think of them as the guardians of the gates to Paradise, forged in ivory, iridescent and brittle. Together, they helped me discover the maxims of players (supposedly) that I will cover.

I deconstruct their psyches using their behavioural patterns I observed during our entanglements. So, yes, this is an exercise in psychological analysis. Even if psychologists can’t read your mind, I sure can try.

I am oversharing insofar as I believe there are lessons for my readers to take away, but you make of it what you will. Also, it’s a form of closure for me. I doubt I’ll ever write about them again following this post because I’ve taken everything I could from them. It’s time for me to move on, too.

A forewarning because the possibility of them reading this is never zero (I adore you, my orbiters): you will not like what’s coming. You may disagree with my interpretations, and that’s okay — either way, you ultimately have no say because you relinquished your privilege the moment you disrespected me as a fellow human being. Typically, I would offer my loverboys the possibility of taking it down if they were uncomfortable, but no such option will be offered this time.

Why? Because you shouldn’t be here.

What you can take away from the following, though, is that this is an attempt to implode whatever relationship we had or might still have. I don’t write without anticipating the consequences.

I wish you the best, nonetheless.

Ivory Guard A

Context/identifier: We had a prior friendship. He reached out to me to restart, and I reciprocated. We both acknowledged that we were not in good emotional places then.
Bond: We had an intense connection, so I believed then, which he later admitted. I understood and could read him.
Green flags:
- He respected my boundaries (for the most part), which is why I gave him so many chances. Yes, the bar was low.
Orange flags:
- He would never directly admit his feelings for me. I started noticing it in the small things like him refusing to acknowledge I was hot or skirting the topic when I teased if he was obsessed with me, even though all signs were flashing in that direction. I did not like that, because why do I have to slave away like a dog for your approval when I could get it elsewhere easily? But I persisted, trusting that he would eventually trust me enough to overcome his insecurities.
- He carelessly made promises he did not keep. Don’t make promises if you cannot follow through.
How he messed up: He ghosted me out of nowhere a month into our budding relationship, which involved a substantial amount of flirting (i.e., me saying whatever I wanted) and whatever tension.
- By the way, people do not accidentally mess up stuff like this. Severing a relationship is always deliberate; hence, no justification will ever be enough.
My response: I was first confused, then upset and hurt. I double-texted him twice, gave up, and took a month to move on.
Whiplash era (when the power dynamics inverted):
- He kept watching my stories even as he maintained his refusal to reply me. I was further aggravated when I noticed — accurately — that he would like the stories that he believed were referring to him. That was top-of-the-line manipulative behaviour, and it disgusted me.
- It didn’t have the effect he intended, though, because our king did not realise that babygirl here had options and already had someone else (of course). LOL. So all his behaviour only resulted in my amusement to no end.
- I engaged in retaliatory offense by kindly informing him (through public means since I knew he was watching) that I was not, in fact, talking about him.
- He proceeded to
  - Call me in the middle of the night, possibly drunk (I did not notice because I was wilding out with my friends), before deleting the evidence the next morning
  - Text me to apologise, which I accepted
  - Ask me to go back to him, to which I said no
  - Ask me to go back to him again, to which I said no again
Psychological breakdown:
- I found closure once I figured his behaviour stemmed from him being a coward (at that time, OK; he’s grown since). He did not know what he wanted and needed time to figure it out. I wouldn’t have minded, really, but what disappointed me the most was that he did not respect me enough to inform me that he needed that time and space alone.
- In essence I was treated as an option he thought he could return to whenever he wanted. He thought I would wait for him. But my universe doesn’t revolve around you, you know. I doubt he realised this initially, but the moment he distanced himself, he could never again return to me. Above all, that was the dealbreaker, along with him thinking he could toy with my feelings with his orbiting behaviour. I told you I would win if you dared play games with me, and you still did.
- My readers might think I’m delusional, so let me note that all of my observations above were validated when he apologised and asked me to return to him. Our only difference in interpretation was that I thought we were never together.
Cumulative emotional impact: I never cried over him.
I dedicate Santorini to him.

Ivory Guard B

Context/identifier: We met at a party. I forgot about him following the party, but he caught my attention when he initiated contact later. We agreed to meet before he ghosted me for a good month. (What’s with players and months?) But he pulled the sympathy card and said he could explain himself, so I listened, maybe because I wanted to see the good in him, or because I was naïve. Turns out he had recently broken up with his longtime girlfriend, whom he loved deeply (I could tell) but had a volatile relationship with. They had a dead bedroom, which is notable for two reasons: 1) it is a death knell in a romantic relationship, and 2) see psychological breakdown below.
Bond: In retrospect, we had nothing real. Most of what I felt towards him was rooted in my projections of what he could be, perhaps because he looked like an angel. But a pretty face is just that (since we’re already at this level of disclosure, I might as well say the men I met on Hinge subsequently put him and me to shame). I’ll never know what’s inside his shell; maybe I wouldn’t have liked it, and I suspect now that I probably wouldn’t.
Green flags: none (!)
Orange flags:
- From the very beginning, he only seemed interested in my body. But see psychological breakdown below.
- He also carelessly made promises he did not keep. By then, I was wise enough to know that the moment he broke our promise — we even did the pinky seal! — I was nothing to him.
How he messed up: He insinuated that we could be something more. Then I slept with him, and then he proceeded to withdraw rapidly in the days that followed.
- I had not realised this yet, but looking back, I would still have slept with him even if he had been honest that he had no clue what he wanted. I knew from the moment I saw him again. Indeed, he was the one who taught me to compartmentalise sex and love. I realised that if I didn’t do so, I was setting myself up for a world of pain.
- And in case you guys think I am a damn homewrecker: I have principles, OK. I ascertained that they were separated before I slept with him, and I would not have done so otherwise. Their relationship is doomed either way: even if he returns to her in the future, they will not be happy together.
My response: I did not pursue the relationship and let the conversation peter out, as he intended. If he didn’t want me enough, I would respect his decision. Later, in my Hinge era, I would decisively inform men that they didn’t like me enough and end our liaison, but I didn’t do so with him. It doesn’t matter because the outcome would’ve been the same.
- Interestingly, my predominant emotion was disappointment more than sadness, unlike with Guard A. It was more like, oh, he’s just like the others. Haha, oh well.
Whiplash era (when the power dynamics inverted):
- He continued watching my stories even when it was clear we were nothing (ugh, why do they all do this), which annoyed me. What do you want from me? It was affecting me, so I blocked him. I realised I had moved on when I was zoning out one fine afternoon and couldn’t recall his name.
- So I unblocked him since he didn’t matter anymore. And guess who came back that night? Let me note here that he is an aggressive orbiter. When you block and unblock someone, they automatically unfollow you. He was not following me anymore, which meant he was actively searching for my profile and watching my stories. If that’s not preoccupation, what is?
- At some point, more than anything, I felt sorry for him. I don’t know why he was still hanging around. (Maybe I was too hot to let go?) But I wasn’t going to help him by blocking him. I did write to my orbiters to him as a final grace — it was written for my orbiters in general, but he leads the pack. You can be the alpha male in this case if you like being one so much, baby.
  - I believe he read it because he stopped watching my stories after that. I might be overthinking, but the timing was too coincidental.
Psychological breakdown:
- Though not necessarily with me, I suspect he was looking for love (surprise!!!). To be brutally specific, I think he was seeking love via sex because he did not know how else he could receive love. It was all he had known. He was aware, consciously or not, that his ex-girlfriend did not love him as much as he loved her, and it was staring him in the face every time she denied him sex. Despite knowing this, he could not move on from her. So his compensatory strategy to reaffirm himself as someone worthy of love was to find a replacement — oh look, that’s me!
- I also suspect he has not reached out because I have established in no uncertain terms that I do not want him in my life, not after he betrayed my trust like that. That, or he’s not as optimistic as Guard A. We will never know for sure. But his feelings towards me are irrelevant — the only thing that matters, and has ever mattered, is that he did not act on his feelings at the time.
Cumulative emotional impact: I never cried over him.
I dedicate Evergreen to him — the parts that hurt. The lovely parts, I dedicate to my husband.

Players, Deconstructed

I defined players as the following in guide #5:

Players. Typically men. Players are not interested in seeking love with you — they only want sex.

What distinguishes this category of daters is their strategy: they masquerade as the genuinely seeking type, but this is only a ploy to get you in bed.

In other words, they prey on the (female) weakness in conflating love and sex to obtain the latter.

I realise that the definition applies only to Guard B (because I did not sleep with Guard A), and hence it is insufficient. I expand on the definition below, which provides a fuller picture and allows for the inclusion of women — namely, insecure people who date recklessly but fail to commit fully.

Notice how the definition is worded. It assumes that players do not seek love with you. It does NOT mean they do not want love. Put another way, even players desire to be loved. Whether they deserve it from you is an entirely separate matter. The point — and this perspective frames my entire argument — is that almost all of their behaviours can be explained by the fact that they are seeking love.

No player operates outside of the rules. Rather, they have mastered the rules and are exploiting them to their advantage at the expense of others. That is why when we speak of players’ behaviours, it is oftentimes layered with contempt, because we all recognise that they actively hurt others. And don’t think for a moment that they’re unaware of how they’re perceived — anyone with sufficient self-awareness, which is essential to play the game well, knows what other people think of them. Nonetheless, they persist in their maladaptive behaviour because they see no other way forward. This is, in turn, because they have demons they are unwilling to confront.

Players are fundamentally insecure. They want love, but instead of being honest with themselves and others, they inadvertently hurt everyone involved because they cannot bring themselves to do so. Whether the insurmountable barrier is their ego or emotional immaturity, they believe that the risk of honesty outweighs its benefits. Hence, they lie to get what they want, or they engage in escape behaviours when push comes to shove.

Nobody, not even players, can entirely separate sex and love. I have described players as professionals at discriminating between the two, but even they are not invincible. When you sleep with someone, no matter what, you are giving a part of yourself to them forever. This fate is inescapable as long as you are a being with the capacity for an emotional bond. The only exception to this would be if you’re hollow inside — I mean, you can’t give anything when you have nothing. But everyone has something, even if they refuse to admit it. I did, and so did Guard B. That is why he lingered longer than he should have.

For the twentieth time, I could be wrong. But as I have demonstrated repeatedly, I try to see the good in everyone, even men who have hurt me. Love is a boundless resource; it can be given over and over, and it will eventually be returned to you.

When you genuinely love someone, you can ironically break them with it.

Maybe break is the wrong word; rather, if you are willing, you can help them grow with you.

The karmic fate that awaits a player is that because they are paying attention to the wrong things, they are bound to realise, only belatedly, that they let the thing they were looking for all along — unconditional love — slip by unnoticed.

Love is what they need — but won’t ever have — until they come to terms with themselves.

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

gwyn’s guide to hyperoptimised dating, #5 (rules of engagement)

1st Aug 20241st Oct 2024 gwynethtytLeave a comment

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

Hi. How has your love quest been? Good, I hope, with my wonderful guides. LOL

Today, we detail Gwyn’s rules of engagement, namely how to (1) decide who to convert from texting to in-person meets and (2) suss out the ones suitable for you from your meetups.

Before we begin, I have a little silly activity for you. It ostensibly helps you to determine how many people you should meet given some rules you set for yourself.

How Many People Should I Date? (365!?)

Before my time on Hinge, while doing the important preparatory work, I found this hilarious calculator which calculates (using math) how many dates you need to go on to find an ideal partner. Please try it and log your stats so you can look back and laugh at yourself like I did.

It is based upon the optimal stopping rule, which advises that you spend the first 37% of your dating period evaluating potential partners (“data-gathering phase” to, well, figure out what you want) before committing to the next person who surpasses all previous ones.

Here were my stats:

if I’m willing to go on 3-4 dates a week (yah I was crazy, it’s not feasible in the long-run)
and want to find an ideal partner within 2 years (haha, 2 weeks [snorts])
settling with the best possible partner
with chances of rejection being 10% (yah I was optimistic I admit. 50% is realistic)

I need to go on 132 dates and let them go no matter what. Then I’ll have a 34.6% chance of finding The One from the total pool of 365 dates.

Insert a massive “your mileage may vary” comment here because this is a rational solution to an emotional problem. Logic is annihilated in the face of emotion. When I met my man, I was so sure about him that I dropped all future prospects immediately. If anything, it could guide estimating how many people you could meet given the effort you’re willing to put in. Aside from that, it’s just for fun.

Anyway, it’s time to YAP.

The Texting Stage, Our Infamous Friend

We assume you have converted a lucky few from dating app to text platform based on your initial impressions. So, we move into the next gear — ahhhh, so exciting!!!

Text Away to Prune, You Must

Don’t be afraid to double-text in moderation. It indicates interest, and if they liked you back, they wouldn’t see you as desperate. And it’s good grounds for elimination. I used the three-strike rule: you’re out if I double-text you more than twice. The third one is a parting message (see guide #6), and no take backsies~ (so it takes only 72 hours to DQ a prospect, wink). Remember: there are no bad texters. There are only texters who don’t like you enough.

Every single text should represent your authentic self. Skip the formalities. Speak like you would speak to your friends. Be polite, of course, but not to the point of being overly reserved. Be respectful but not detached. Send stickers and hearts. Be a little bit careless. It’s not a work interview — we’re here to have fun. Live laugh LJ, OK?

Know when to share what — match their level of reciprocity, but always give a bit more to keep the conversation going. And then more, more, more, until you burrow yourself into their hearts and leave your indelible mark. Your love is not a crime.

Use your gut feeling to decide what’s right. DO NOT trauma dump until you’ve met; sudden excessive disclosure is a turn-off.

People who like you do two things beyond bantering: (1) send you telebubbles of themselves and (2) tell you about their day without you asking. But this does not mean they (will) love you; it could very well be love-bombing behaviour. I remember the fun calls I had with Captain, who did not love me in return.

Eeny, Meeny, Miny, Moe, Who Shall We Meet Next (“Full Conversions”)

Meet only those you have established rapport with.

Don’t jump the gun no matter how high-value they seem (if you missed it, read the story featuring Guy #5; that was a bop). If you’re direct, just say you’d like to get to know them better before scheduling a date. If you prefer to be indirect, say you’re booked until next week. If you’re a woman, do not explain your schedule. If you’re a man, explain if you want brownie points. Ultimately, both parties will set aside time for each other if they are keen on meeting, which is natural if you have built a bond via texting.

OK I will admit I only spoke to My Man for 4 days before meeting him. BUT he is a special case (obviously) for two reasons. First, we had a common interest (jazz), which was a good enough reason to meet in itself. Second, I sensed from the start that he was a decent guy. He was polite, responsive, and showed initiative consistently. I was so certain about my judgement that I considered giving him a kiss by the end of the date before the date began. Yes, I’m crazy. And yes, of course I was right.

Rostering

To have a roster is to juggle multiple prospects at once, at least on a texting basis. I don’t know how common this is, but I suspect everyone does it to some extent. My roster had 3-5 serious considerations at any one time. And all the men I met were rostering. So there’s nothing to feel insecure or threatened about since everyone does it. Rather, your goal should be to climb to the top of that list (no compliment matches being told that “you’re #1 right now”, LOL. I’d better be!)

Funny one: high-value men do not just roster, they sometimes even deconflict. I matched two men who I discovered later were literal besties. They had an internal agreement on who would get me (although I had a say insofar as I only replied the one I liked more)!!! What is the world coming to!!!

Even discussing your rosters can make for a fun meta ice-breaker. A handsome guy asked me about mine, and I told him oh, you’re #2 because I haven’t talked to you much. He sweetly informed me in turn that I was #3 for a similar reason — because he had met someone else earlier than me, so they had a time advantage. But how long you’ve known someone is not predictive of how intense the connection will be; rather, it is the quality of your conversations.

Also, you’ll never know how intense the connection really is until you meet them. (My Man was not #1 in the texting phase. I then met him and decided he was #1 for the foreseeable future.)

First Dates!!! ❤

Dates as Marriage Interviews… or Not

When someone from a dating app agrees to meet you, they are looking out for three things you can potentially provide them.

Love, of which there are two subcategories:
- 1a. Romantic love
- 1b. Friendship
Sex
Financial benefit / a free meal (rare, included only for comprehensiveness; if you do this, you’re silly)

Gender differences

Men are always 2, and sometimes 1a&2.
- Men sometimes want love.
- But my guess is that men always want sex. In the sense that, even if he does not initiate any sexual contact, he will always welcome it if you offer. Let me say it again — always.
Women are generally 1a, and sometimes 1a&2.
- Women can be looking for sex, too.
- But we assume that a majority of women are primarily looking for love on the basis that they cannot compartmentalise sex and love as cleanly as men can.
3 is a Shiny Pokémon that operates on rules from a bizarre universe. They are not dating to find love. They are looking to sell insurance (both men and women) or eat out for free (typically women). If you have the misfortune to meet someone like this, end the date ASAP.

Extrapolating from the points above we can identify subtypes of daters based on their intentions (which, interestingly, aligns somewhat with Hinge’s dating preferences).

Dater subtypes

Genuinely seeking a partner (1a&2). This person’s primary goal is to determine if you will be a good long-term partner for them. Sex is a bonus but a secondary afterthought.
- The friendzoner (1b). A special breed. Basically, they go to meetups intending to build a connection with no possibility of romance. Friendship could also be an outcome of marriage interview failure — a coup de grâce — if 1a (love) doesn’t work out, but they still find their partner interesting as a person.
Players (only 2). Another special breed and the most interesting of them all. Typically men. They are not interested in seeking love with you — they only want sex*. What distinguishes this category of daters is their strategy: they masquerade as the genuinely seeking type, but this is only a ploy to get you in bed. In other words, they prey on the female weakness in conflating love and sex to get the latter.
Clowns (only 3). More likely to be women than men due to social norms.

The differentiation is important because their behaviours will differ if you observe closely.

3 is obviously the easiest to tell. Out of nowhere, they ask you about your financial goals. We move on.

What we care about is how to separate a player from a genuine seeker.

Differentiating genuine seekers and players

Genuine seekers’ behaviours. My pet name for them is “secure (wo)men”.

One thing I’ve noticed about men who are (really) looking for long-term relationships is that they cut to the chase. They talk about preferences and deal-breakers early. They help you decide in a collaborative manner — they do not lead you on, they do not play games.
- One date (I will always have a soft spot for him because he was so kind to me) saw the way I looked at two kids walking by — and he immediately mentioned he didn’t want kids. This was half an hour into our first and only date. I remember turning my head, my line of sight fixating on his ethereal, dark eyes, and the anticipatory grief flooding my heart. Our relationship was doomed before it began, though I still enjoyed my time with him. (This is why you should put your family plans front and centre on your profile.) He later told me I would be a good mother. I believe him. I’ll be happy for him, too, when he eventually finds the one for him.
Genuine seekers are upfront about what they want. For example, someone told me he was unsure about me as a prospect but still wanted to sleep with me. I think “unsure” is a poor word choice if we follow the rule that “it’s a no if it’s not a hard yes”, but it remains superior to lying.
Other characteristics
- They respect your boundaries. If you say no, they accept it, no questions asked.
- They are NOT AFRAID TO SHOW THEIR AFFECTION!!!!!!!!!!!!
Essentially, genuine seekers are rational machines. If you understand the rules they play by and you mirror them, they will respect you.

Players’ behaviours. AKA red flags to look out for.

Players are identifiable by their lying. Therefore, their insinuations of love, intended to bait you, do not match their actions.
It’s a terrible sign if all lines of conversation inescapably turn sexual as the night progresses, in the style of all roads leading to Rome. He’s asking about your body count. He’s asking when you had your first kiss or lost your virginity. Boring shit like that. Correct answer: not your business until right before I sleep with you. Questions that seem out of place, that make your inner goddess tilt her head. It isn’t the right time, and you know it.
Hot take, but you can kind of tell from the way he touches and looks at you (!).
- Did he hold your hand before he touched your thigh? If he jumped straight to the second, you really only have one decision left to make: whether you want to sleep with him or not. Because he has made the other decision for you: he does not want to date you, and it’s unlikely this will change. One-night stands do not hold your hand. Whether you go home with him, you are leaving without him.
- Your first kiss with him — was it innocent or indulgent? Genuine seekers kiss like the former, while players kiss like the latter. Why? Men interested in you care about your opinion of them, and this desire for approval debilitates them. But players do not care.
- The hunter’s look. You’ll know when you look in their eyes. Players look down at you, chin tilted up ever so slightly (it’s hot though; I’ll give them that). This is the hunter’s look. You win if you can turn that look into one of confusion or admiration. In comparison, a genuine seeker looks at you more affectionately… like how your friends look at you when you laugh.
- On power dynamics. Related to the above, players usually enter thinking they have the upper hand. This is not necessarily an unjustified assumption — they think this way because they have an established record of winning past games. So it’s on you to put them in their place. Once you call them out on their behaviour or act in an unexpected way (e.g. turning down their offer to fuck or publicly shaming them on your blog, HAHAHA), they’ll be neutralised — and you’ll know when it happens. You don’t have to do this with genuine seekers because they will be treating you as an equal in the first place.
BTW, if their texting behaviour suddenly ceases the day after you sleep with them (regardless of date #), the relationship is over. LOL. There’s no need to ask your friends what they think is going on. You’re hearing the death rattles of a hunt because it is the withdrawal phase. There is nothing much you can do at this point but come to terms with it. Sorry. Get into discard and recovery mode. If you want to avoid this problem, don’t sleep with them (YES THIS IS COMING FROM ME).

*Caveat: I portray players as one-dimensional creatures, but people are not that simple. However, that is beyond the scope of this post. If I think about it more, I might write #5.5 (on players).

On EQ and IQ evaluations

IQ and EQ are pivotal considerations in seeking long-term partners. At the risk of sounding obvious, let me state upfront that people seek smart and emotionally savvy people as partners — this is a fact of human nature — but let me also qualify this.

People tend to attract and ultimately choose others similar in IQ and EQ levels. Relationships with significant discrepancies are unlikely to work out because what is there to build when you fundamentally don’t connect over your ideas or feelings? (So yeah, even though Hollywood likes to romanticise the “opposites attract” concept, it is a myth. One exception to this rule, though, is when one partner is socially dominant and the other is submissive.)

More importantly, I would argue that EQ is more important than IQ (though, of course, they are correlated). The problem is that you can’t tell someone’s emotional intelligence level off the bat from their profile, as opposed to conventional intelligence, which you can infer from their work and education. You have to meet them to know. Or you at least have to text them for a relatively extended period to see how they respond to situations and what you bring to the table.

Characteristics of high EQ people, based on my observations:

They know how to make someone else feel comfortable around them. They can “read the room”. They are constantly observing and assessing their partner’s cues to infer their emotional state, which they then use to decide the next best action to respond with.
- Your body instinctively recognises when your partner is doing this. It’s the in-sync feeling — when you can’t find a word, and they complete their thoughts for you as if they were inside your head the whole time.
- Remember I said My Man treated my bruises? He was like, oh, don’t scratch your legs! And why do you have so many bruises! Let me apply cream on them for you! Here’s why I was shocked: I was hardly aware of my bruises. Exceptional attention to detail.
They are excellent with “recovery” situations, i.e. when a conversation is going awry or there is an awkward situation. Again, it is a lot about awareness — because I know your intention, I can play along with it to save us both from embarrassment.
They remain calm in stressful situations. Because they can reframe a situation and generate solutions quickly. Sign of a high-functioning prefrontal cortex and good emotional regulation.

Contrast with when they lack this awareness. Guy #5, for example, lacked this (sorry I keep dredging this guy up, my sample size is limited and will no longer increase, unfortunately), at least in the few hours I was with him. He could not tell that I did not feel safe around him. And I think it would have been obvious if he was paying attention. I wasn’t physically receptive to his advances, though hell, I was doing my best. If we assume that he wanted to sleep with me, he failed because he mistimed his steps, which in turn was because he couldn’t determine when to do or say what accurately.

Finally, the Rules of Engagement

Friends first, lovers later. Don’t meet anyone you wouldn’t have as a friend. Your lover is going to be your best friend (potentially for life!).
Be interested in them and show your affection confidently. Don’t be a wishy-washy person who blows hot and cold. If you wouldn’t like to be hurt, don’t make others suffer for your insecurities. Go away and work on yourself.
- Secure people like honest people. If you tell them what you genuinely feel and think, they’ll be appreciative and reciprocate.
Similarly, be ready to give your all. This involves intense emotional disclosure when the time is right. You’ll know when. Pay attention to your body and your gut feeling. Don’t share anything that crosses your boundaries, but be willing to step out of your comfort zone.
- I think some of us do not give everything initially because we are afraid of 1) being rejected and 2) seeming desperate (which ultimately leads back to 1 anyway because you are afraid that seeming desperate will lead to rejection). But people who want you will never see your affection as desperation.
- I also understand that everyone is afraid of being vulnerable (myself included) but consider this: if the two of you are going to end up together, wouldn’t they eventually know all your flaws anyway? So be brave: your flaws will be loved by the people who matter because they are what defines you.
Remember that time is a commodity, especially so for working adults. When someone makes time for you out of their busy schedule, remember that they are giving you a lot of grace. So help them make the best out of it. They will be grateful.
“Have no expectations” is something I’ve been told repeatedly, but let’s dive deeper. Act like you’ll never see them again, and you’ll be surprised at how many doors open. Recognising the transience of your connection leads to treating others as best as you can, rather than casually or non-committally because you think “we might meet again”.
Active listening. In short, active listening requires that you be present. That means put your damn phone away and listen to what they have to say. LISTEN without planning to respond. Just pay attention and try to imagine yourself in their shoes. Ask questions to clarify and understand their perspective. Your curiosity will come naturally.

So get out there and have a smashing first date. And if it doesn’t work out? Don’t worry. I’ve got you covered in guide #6, where we’ll discuss how to sever a connection — kindly and maturely.

Until next time, babygirls x

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

gwyn’s guide to hyperoptimised dating, #1.5 (sex and love: the hunting ground)

18th Jul 202413th Sep 2024 gwynethtytLeave a comment

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

In this exercise, we invert the gendered rule of sex before love:

Men do not sleep with women they are interested in on the first date.

Now, we apply this to ME (you).

If I sleep with a man on the first date, it must mean I am (you are) emotionally ready to disqualify him permanently. To see it through is to certify with a seal that I do not expect to see him again, and I’ll be fine if I don’t. In fact, I must expect to never see any man that I sleep with again if we do so before any binding commitment is made. I ate him up and got what I wanted; that’s a full hunt completed.

They took what they could, and so did I.

If they do not want more, neither shall I ask nor desire.

Don’t turn around, don’t blink twice.

This does not mean I view men as “prey”. I’m not delusional (I think, haha). I respect them as human beings like myself. We are equals; coercion is never involved (or the police will join the party).

But I will reciprocate how they treat me. Some men (not all) act like this is a game and women are prey to be devoured. There may be no coercion, but there is always persuasion and manipulation in human relations. They think that if they go through the motions and “play the game right”, women will willingly fall into their arms — and they don’t even have to commit.

But there are no free lunches in this world.

They think they’re the hunters; they don’t realise I own the hunting ground.

And on these grounds, babygirls — contrary to my tagline — love is not a game.

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