I’ve never been very good at dating. But the more I attempt it the more I notice my own advantages and disadvantages.
And this next sentence might sound very harsh but anytime I start to slip into any kind of dating depression I remind myself that I am not a man. And because I’m not a man I have no real ideas on how hard dating can actually be.
And then I take a moment to feel grateful.
A question that floats through your mind might be why I think dating is harder for men.
I think a lot of that is intuitive but I can say my own personal associations on what I think is hard and how men experience more of it and at a deeper level.
On some occasions I’ve experienced that feeling of worthlessness. I’ve experienced it enough to have strategies around battling it.
But it does have its little triggers. Rejection is one such trigger.
Rejection has levels. If someone I’m not that into rejects me I don’t really much care.
But why is it I don’t much care? Why is that?
Why do I only care when I’m really interested?
Partially because I have plenty of confidence on my overall attractiveness. And I have plenty of confidence on my overall attractiveness because I have plenty of evidence.
So when a man rejects me and I’m not super interested I know it’s not a reflection upon my place within the world. So many people hit on me. I know I’m hot or at least hot enough to pass by that base level of desire.
Men are not my mirrors when it comes to my looks.
Men are also not my mirrors when it comes to my likability. I have a lot of friends and get along very easily in most environments and I get along with a very wide range of people. I know I’m very likable. I have plenty of evidence.
So then why does it trigger my feelings of worthlessness when a man I am really interested in rejects me?
Because at those deeper levels of interest where I like a man enough to want to have him consistently in my life, I’ve experienced a lot more rejection.
Rejection creates mirrors.
Little distorted images of what is not good enough.
And some things actually are not good enough.
At one point in my life I was a destructive tornado of chaos (chaos tornados are fun though.) being rejected for deeper levels of commitment was perfectly reasonable.
I recognized such a thing and did my best to claw my way out of the center of that tornado. Slowly I’ve become functioning and I’m now reaching towards high functioning.
But I did so from a place of self reflection. And rejection provided the mirrors.
Rejection isn’t quite so bad actually. Most people if they think deeply on it will not be all that upset by rejection. What’s upsetting is what rejection implies.
What it can imply if we have no other evidence is feelings of worthlessness. Which is quite a deep level of excruciating pain. It is an idea that stretches very far into time and very deep into ourselves. That we have nothing of value to offer anyone and therefore will forever be ignored or avoided.
And for the most part men experience feelings of worthlessness far more frequently than women do.
Especially within the dating world.
How do I know that?
Because. I know what it takes for me to feel attracted to a man. I know how many men I have rejected and I know for what reasons I have rejected them.
I know how incredibly harsh and unforgiving my own desires are. How dismissive they are to anything that does not align. I know how many things are worthless to me that another human being has built their entire identity around.
I know the nature of women.
If I were to give any advice to men rather than give it myself I’ll direct them to people more qualified.
Gatekeeper by Shawn T Smith is a fantastic book for a man to read.
I’d direct them to Robert Glover or Arthur Brooks. Both incredibly helpful for men especially.
If I’m honest I don’t have a clue how the male psyche works. I have some vague ideas and little guesses, but it’s definitely a foreign world.
In my own dating life I’m still not entirely sure what I’m doing. I don’t really know that I’ll ever be successful in the sense that I get married and have children.
But I know I don’t have control over that.
If I really wanted children yes, I could go have them of course.
If I really wanted to get married I could find a man that wanted to marry me, yes.
But that is desiring the outcome more than the journey.
I’m a journey person.
Making Mektoub was more fun than it being a success.
Falling in love with my first boyfriend was worth it ending.
Doing porn was worth its consequences.
So with my own dating life I’m going to walk the path I can see and just take what it gives me.
By that I suppose I mean I’d rather fall in love than get a result.
Which essentially means I don’t get to choose whether or not I get married or whether or not I have a kid.
That becomes a man’s choice. I choose him and then he chooses everything else.
I’d say most women these days don’t like that idea. And it goes deeply against a lot of the dating advice women receive.
And my own sanity can be questionable in the sense that I can be a tad eccentric and a bit too open. Lots of my ideas are radical and can lead to total ruin.
So I certainly would never suggest anyone follow my example.
But.
Deep down that is what a lot of women do want. To follow desire and relinquish control. Because it’s very hard to have both.
I honestly can’t think of a single example where I’ve had both desire and control.
Desire and trust yes. But to trust is to not need control.
Jess lanai 
5 responses to “How to date part 9”
Always good to see a new post pop up, definitely enjoy getting to read your perspective on this stuff.
I can relate with you view on rejection. Rejection itself doesn’t scare me off, but getting back into the swing of putting myself out there after not dating for a while definitely feels odd. When you’ve built a solid level of self-respect and know who you are, the hardest part isn’t the rejection. I feel like it’s the friction of dropping my hand and guard and opening up to women again. My bigger concern isn’t taking a straight up “no, in your dreams,” it’s honestly when I’m sinking time and energy into someone who is afraid to just be straight up about their intentions from the start. I’m a man of action at this point in my life when it comes to directness. Especially with my view on dating now.
I will say, when it comes to even knowing who’s interested in me? I sometimes have to be hit with a sign that’s the size of a barn door that says ‘I’m flirting’ or ‘hello, I’m interested’ because I spent so just being used to not feeling seen or into. Not even about my looks, I know I’m not ‘into myself’ yes, I’m hygienic and keep myself clean, but more so what you had touched on.
Being chosen or just finding someone because they’re nice is one thing. But that true chemistry, connection? I’m a fucking SUCKER for a slow burn romance. I want to feel every movement of it, but with knowing where it’s heading.
Nothing has to be rushed but intentions always clear and actual passion and real building of a bond. That’s what I’m trying to find. I knew that’s not what was in my last marriage. Which has given me a deep sense of comfort and knowing the direction i want to head with the person Im with. If I just wanted to check a box, I could go get married again and have kids tomorrow. But I don’t want a generic outcome; I want the specific, actual person I have in mind. Having that clarity makes me patient, because me settling for a shortcut misses the whole point.
All of what you’ve said has been super insightful and really interesting to read. I really love your takes on rejection in general and how it’s definitely not like a lot of people in a way I can relate to.
What you wrote about desire and relinquishing control makes a lot of sense. I like being a leader in a relationship and taking the wheel, but that only works when there’s open, honest dialogue from the very beginning. My goal as a man is to handle business, build stability, and take care of things so my partner has the freedom to focus on whatever she wants in life, supported, not micro-managed.
Anyway, I always appreciate the food for thought. Awesome read and post.
– J
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Dating is very, very odd. It’s really destabilizing and people have gotten much worse at social skills I’ve noticed, so it’s just a very odd thing. I don’t even know if it’s something that’s healthy to get good at. I want to find more ways to get to know people more organically but I’m not sure how yet.
I personally am doing my best to put much less energy into it. Much less thought, much less emotion, I try to make it fun and low effort as much as possible. Because the note put into it the more it’ll mess with you for sure. Try to make it an after thought.
I try to be as busy as I can with other stuff and just fit dating in when I can.
You’ve got to remember to that you are still so young, you’ve already been married, you do not need to rush to meet someone.
I am again going to recommend gate keeper. That books is fantastic for men.
And I personally think people putt too much on the very beginning of a relationship. I don’t know, it’s impossible to know where anything will go. You can think a person is great and be totally wrong and vice versa.
The things grow with a person can be insane. Red flags can really be green flags and vice versa.
People often just want the plan they made in their head to be the one they get. But the head makes up so much stuff that just isn’t true.
But it’s hard once you form a bond with a person that’s usually very hard to let go off.
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Right, I don’t necessarily want to build up a RAP sheet of people. I totally understand that feeling of wanting to organically find people. It’s a beautiful thing when it does happen organically, both friendships and romantic relationships.
I honestly think that’s the best approach, it’s really not needing to be more complicated than it could be already and I agree that putting too much pressure on just getting into a relationship, just to be in one? ruins the fun. Me keeping life full/busy is the best way I’ve been able to stay grounded.
I do Work 40+ hours and do anything and everything I can get myself into when I can, so that’s extremely helpful.
Working out, and Duolingo, cooking new meals. Watching twin peaks now apparently, because I’ve already spoiled it for myself enough through your posts so I mind as well start watching it all.
There’s plenty I do to keep myself happy, and doing things that make me, me. Remembering that side of myself. It’s been cathartic for sure.
But I definitely need to read gate keeper, you’ve told me more than once at this point so I have no excuse lol, and you’re definitely spot on about people having this script in their head instead of the actual person in front of them.
Keeping it low-pressure and just letting things unfold naturally? is the move.
But yeah, once you form a bond, that’s very true too. It can set unhealthy expectations for sure and make things complicated at the least.
I seriously appreciate the book rec, I’ll adding it to the list. And always love the recs
– J
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Your piece was very well written and you made your points briskly,but …..You have confidence in you ability to attract men,yes as you said you have experience but all your examples were of men .It could all do with an objective Female view point.
You seem very confident in your ability to do anything you want with regard to relationships you seem to be in control whether the relationship is temporary or a lasting one,i doubt it will always seem like that.You are an intelligent woman,but you are talking to a a lot of men who are not nearly as self confident as you seem to be.
I am taking this line because it needs to be taken.
You attitude to having kids was also revealing having children would make you a lot less of the focus .
Speaking for myself,i do not have as much relationship experience as you seem to have,i have some good and bad nothing that i lose sleep over.
Your piece was well written and well put but ……
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Jess,i apoligize for the tone of my post written on 6/8/2026 ,I was way too harsh you have a lot in your arsenal,you go GIRL ! obviously you are a woman but you get my point .
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