The first thing you have to understand is that the rules of dating, or the mainstream dating-coaching or pick-up advice is for men who think with their dicks. Aka, men who aren't like you! This entire dating-strategy is to get laid. What the actual point of dating is and where this is all headed is irrelevant to these individuals, it's just 'me want sex so me approach women'. 
The reason you're not like this, is because you have higher standards in women. You don't see 'experience' with women who aren't that feminine as worth it. 
A very important point to note here, is that in the mainstream, dating, relationships and marriage have been romanticized to no end, to the degree that people equate these things to 'love'. They will just use the word 'being in love' when they're just in an arrangement that logistically works. There is little to no awareness of genuine compatibility in relationships when it comes to future plans and aspirations. 
So, what you should do, is you should date correctly. Meaning, you should date to find someone compatible! Which is the actual point of dating. Ignore all of the pick-up guys bragging about how much they scored with women, understand what you want in a woman and date strategically. That'll make dating smooth and effortless for you. 

I feel identified. I got rid of the monster in one day, then it came back, but i already knew what it was... it was never the same and now it's not even a little monster. It was a short time ago, maybe half a year. I took 2 g of mushrooms, and I quickly saw that the thing was going to be unpleasant. As you say, I took a beating from the monster. I endured it stoically. Suddenly, in the middle of the mental torture, something became clear, obvious, evident. out of the void, out of absolute nothingness, my experience arose like a perfect diamond, something of celestial beauty and perfection. and there was "me" labeling, gutting that gem opining that this and that should have been, perhaps, a little different. in a matter of a second, the monster lost its poison completely. there it was, fluttering around me like a black and white movie, lifeless, a dead thought, nothing more. my mind was released, like never before. overall lightness. I went out into the street and the beauty of the sky, the color of the people walking through the center of the city, street musicians, was dazzling, wonderful. At the time, the little monster returned, but for a short time, weak. Yesterday for example, I came back driving 7 hours from a trip, and not a thought of those crossed my mind. something unthinkable before. the monster is nothing more than the should be activity that you print to everything. It is you, who from a wrong, aberrant perspective, print that stupid demand, learned, transmitted by others, of how reality should be. reality is, and "you" must remove your dissonance from it 
make the should be match to the micron with what it is, because this is the reality. what is is what should be. this has to be seen beyond logic. the monster is the dissonance between what should be and what is, an activity that you do continuously

Because truth cannot be hidden, denied, or avoided indefinitely. Falsehood and illusion is always a finite game. Falsehood and illusion is unsustainable because it is self-contradictory. Falsehood lacks structural integrity, therefore it always collapses. This is God's mercy! If God allowed falsehood to have indefinite structural integrity God would be the Devil.
Truth = integrity
In other words: God must be itself. God cannot not be God. Because Truth is itself. If Truth was not itself, it would be falsehood, which is absolutely impossible.
You're afraid of your own enormity.
It's hard to accept that you enjoy raping children.

Don’t underestimate that. That is so to speak the ‘true’ ‘work’. For one being honest it is only a matter of time before the notion something’s wrong with you is recognized as judgement / just the thoughts or thought activity that it is. It’s just that little bit of relief noticing that each time said thoughts roll around or arise. Don’t hold expectation for breakthroughs, game changers, etc - it’s just about that little bit of relief and more & more feeling & knowing that feeling. The thoughts are apparent. So there might be that relief right now in the thought… ‘there is apparently, as in seemingly something wrong with me’. That slight change is what it’s all about. Not the trips etc. Also, contrary to popular belief, there are no “deep” thoughts. That there are, is just one thought, that there are. Believing such a thought = believing a “big” or “deep” solution is needed or could be on some “horizon”. That “deep thoughts” concept is what leads to the “deep problem” conceptualization of simple self evident feeling. Specifically, it leads to ‘deep thoughts of hate’… vs ‘ok, I wanna let being so judgmental go’. 
Also really be aware of the old habitual tendency to commiserate. Like some people stub their toe, say ouch, and are mindful to be more careful. Pain happens, such is life. While yet other people stub their toe and start googling to connect with others who’ve also stubbed their toe, forming a support group, discussing methods of toe stubbing prevention, how to heal from a stubbed toe, etc, etc, etc mfing, etc, etc. If it feels like shit it’s shit. No need to keep chewing it and ‘make sure’. Just let the shit go whenever the shit arises. 

The more feminine the woman the more she will be attracted to status.
Status sub-communicates that this guy is a successful, proven leader. And that's exactly what the highly feminine craves. That's what "alpha" is: leadership.

For exactly the same reason you treat fat ugly girls as trash.
People are selfish and only respond to those who serve their survival agenda.
A nice guy does not serve the survival agenda of hot women. Women don't need a second pussy.
Rather than blaming women, stop being a pussy.

Keep going deeper.   In a non-dual state of consciousness, consciousness will have realizations.  That is because form and formless will be One.  God realizes what it is. It is pure Infinity.  It is not realizations of finite consciousness, it is realizations of Infinite Consciousness.

The Buddha deeply realized that it is our dharma as humans to awaken. Why would he care, after battling Mara, and seeing through the illusion of individuals?
Because suffering, even within the dream, is still suffering. He realized the origin of suffering, and the path that leads beyond suffering. Enlightened or not, "you" are still entangled in Maya, until you "die". Would you rather lucidly dream, lovely and free from suffering, or disconnect entirely in apathy?
Realize that we created This for a reason. Also realize that suffering, within This, is only necessary, until you realize it isn't.

Glimpses are terrifying to the ego, yes. But this fear is what shows you that you're on the right path, because this fear is the ego disintegrating. It's the egos last defense mechanism. It will make you believe that you're going hopelessly insane or that you're Going to die.
That's right! You're going to die. And you will lose your mind! But only the ego-mind, only the thought of ego.

The only reason why to explain this stuff not to demonstrate myself, there is no me, i am you. And you are suffering. You will need these words. I am helping myself. That what unconditional love is. Otherwise i dont need to explain to anyone, i have already know that i have never born. Therefore Listen me! 

If others aren't real, then there is no me doing anything. There is only you imagining me.
What's happening here is that you are imagining duality because you are trying to keep yourself asleep. You don't want to wake up.
It does matter, if you care about awaking up.
All perspectives are the illusion. There are none. Only you, sitting there, imagining stuff.
You see... you don't really want to fully wake up. You want a comfy partial awakening. Not a full one. A full one would annihilate the universe and everyone in it.

There actually is no such thing as POVs. There is only your direct experience. All POVs are inside your POV.
The concept of Points of View is inherently dualistic. It too much collapse.

I just rolled over Leo's blog to find some hidden old gems that can be quite refreshing to read and watch while he's away.  And don't forget to take action! 
Some of his views may have changed on some of the older ones, but they're still very valid. 
Text Posts: 
https://actualized.org/insights/a-description-of-enlightenment   
https://actualized.org/insights/the-best-mix-for-enlightenment
https://actualized.org/insights/educate-yourself-about-enlightenment
https://actualized.org/insights/whats-the-best-time-to-meditate
https://actualized.org/insights/yoga-ftw
https://actualized.org/insights/nothing-i-say-can-be-trusted
Video Posts: 
2017:  
https://actualized.org/insights/understanding-better-than-academics
https://actualized.org/insights/changing-perspectives-destroys-reality
2018:
https://actualized.org/insights/metaphysics-vs-epistemology
https://actualized.org/insights/all-understanding-is-metaphoric
https://actualized.org/insights/all-understanding-is-metaphoric-part-2
https://actualized.org/insights/skepticism-and-nonduality
https://actualized.org/insights/dont-half-ass-yoga
https://actualized.org/insights/sitting-posture-for-yoga-meditation
https://actualized.org/insights/may-2018-solo-retreat-part-1
https://actualized.org/insights/may-2018-solo-retreat-part-2
https://actualized.org/insights/may-2018-solo-retreat-part-3
https://actualized.org/insights/hawaii-april-2018-late-night-insights
https://actualized.org/insights/mindfucked-in-hawaii
2019:
https://www.actualized.org/insights/miracle-awakening
https://www.actualized.org/insights/ego-collapse-awakening
https://actualized.org/insights/total-omniscience-awakening
https://actualized.org/insights/dpt-the-other-god-molecule
https://actualized.org/insights/sense-organs-are-imaginary
https://actualized.org/insights/do-i-doubt-myself
https://actualized.org/insights/infinite-love-awakening
https://actualized.org/insights/how-to-test-for-self-bias
https://actualized.org/insights/rethinking-human-history
https://actualized.org/insights/tapping-into-collective-consciousness
 
 
 

The self-esteem issue actually plagues most of the world. The many problems we have in society stems from a lack of self-esteem. Most people are just really good at hiding it, but know that you are not alone in this issue. The reason why most of us do anything is for validation from others. Most people who seem like they have high self-esteem are living in an illusion. They only feel that way because of the external validations. If you take away their external validations they quickly crumble into a chaotic mess.
The way to obtain true self-esteem comes from loving yourself as you are. When you learn to accept yourself with all of your flaws, and don't judge yourself for who you are, you will develop a high sense of self-esteem that isn't dependent on any external validations.
What has helped me is a variety of many things I have done. I have made a lot of progress, but I am still far from perfect and still have a lot of work left to do.
Here are some things that helped me:

- Pushing my comfort zone, and doing the things that scare me or make me uncomfortable. I'm still finding ways to push my comfort zone regularly. This has helped me to grow and develop and has boosted my confidence.
- Regular meditation for a period of years. This has allowed me to ground myself and create the space I need to learn more about who I am. This is an on-going practice for me because it is a tool that helps me.
- Learning new things and constantly improving my skills. This makes me feel more competent and less dependent on others to make my way through this world.
- Psychedelics (Really helps put things into perspective and pushes through a lot of your emotional wounds.)
- Energy healing like reiki, and guided meditations.
- Having more confrontations with people, to the point of almost getting into fist fights. Also known as expressing myself more authentically.
You mentioned you fear standing up for yourself and being more assertive. It does feel like you have to fight others to be as you want to be. It's true. In a sense you do have to fight others to be as you want to be. Not physically, but energetically you need to fight. Everyone wants to impose their will on you. The more you express yourself authentically without judging yourself, the better you will feel. That means sometimes your authentic emotions will look ugly to the outside world. Authenticity is not always pleasant. Dare to be more assertive. Dare to be more opinionated. Dare to stand up for yourself and express yourself as you want to. Dare to love yourself.

@fork You are the higher consciousness already. Thoughts, arise “from” / “within”, you. When the next thought to say something arises, instead of reacting, just let it go. Watch a rock, until every thought ‘empties’, for example. Thoughts about the rock arise, and go. Thoughts about life, me, etc, arise & go, like helium filled balloons floating away. Eventually, with every balloon let go, helium is directly ‘experienced’, and so is “it’s” source.

@Raptorsin7 I agree with your sentiment. 
(Sorry for buttin in...)
Reality can’t fall apart. Our beliefs in “parts”, falls apart, and there is wholeness. 
You will feel better for meditating, and you can also inspect the beliefs, thoughts, & perspectives that “got you there” (not feeling good / fear). If I had some self beliefs to inspect, and wasn’t, I might miss how when I go inward, thought stories convince me it’s about the outward, or, other people / the world. As an analogy...imagine finding the awesomeness of True Grey, as a present wrapped with black & white wrapping paper.  
That outward slight of hand via our sneaky minds, is like a magician’s misdirection...and before we notice, we’re looking outward. 
But writing it on paper, or ideally, on the backside of your dream board...now it’s out of the head, and in front of it....where it can be seen, understood, and readily transcended.  (“Inspected”)
And fear turns out to be love. As in, “well I’ll be dammed. I was looking at that like this, because when I was x age, this happened, and I thought I was like this”. “The “bad” feeling what my perspective - feeling was SO unconditional love - it just couldn’t go there with me. That feels like, terrible, when I do that.”  Fear was love the whole time, that “bad” feeling was love...saying “that ain’t true!”.  But, you gotta inspect beliefs like guilt & shame, see the why’s, when’s, you even believed in them to begin with...then barf up that you actually used them to make up fear ? ...and understanding arises...love...feeling is understood, listened to, alignment. There’s really no difference between love & intelligence, same being. Can be helpful to consider. And happy “birthday”!