A guy I was at a party with told a girl he “liked her boobs” and got her number??

This line right here:

"This goes against everything I know about dating and flirting and relationships and women and everything about humanity in general."

Basically sums up my feelings and experiences trying to date as a remotely-socially-conscious man. You spend all this time listening to what women want and what they say they appreciate and then you get into the real world and find out that if you follow their advice (being respectful, reserved, self-aware) all you're actually doing is removing yourself from the dating pool because it turns out women don't actually respond to that kind of behavior. They respond to bold moves like this one.

I have a similar story of an old roommate who was kind of a ladies-man. He was really obnoxious and a bit toxic but I cannot argue with the results because this man went out with so many beautiful women in the short time I knew him and brought them home really frequently. One time he and I were hanging out and he literally walked up to two women who were locked in their own private conversation, barged in, interrupted, placed himself physically between the two women who were just talking with one another, and asked one of them for their number. He got it on the spot and I, like you, was slack-jawed because I can't imagine doing anything that brazen let along being rewarded for it.

I have seen this too. But embodying the traits of being a good person to date pays off in the long term. You're learning social skills that are better suited to a good life than what this guy is doing.

It sounds like a bunch of rubbish, but I think most people and society as a whole come out better when you're respectful and mindful.

I tend to agree and for the record I'm glad I'm not like that guy. But at the end of the day I'm alone and I bet he isn't. I was trying to give advice to my own brother a little while ago and he looked me dead in the eyes and said "You've never even had a girlfriend, why should I listen to you?" That shit hurt. He's not wrong, but it sucks to realize that even if I have the best and least-toxic worldview and treat women super well, no one will take me seriously if I don't have anything to show for it. No one will ever want my advice about life if my life isn't one that anyone wants.

I shared some of my struggles with this same roommate and in his gross smug way he said something along the lines of "That's your problem man, you're too worried about making people uncomfortable or being creepy. You have to just forget about all of that and shoot your shot, and if you make them uncomfortable it doesn't matter, just move on to the next one"

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It's exactly the kind of toxic bullshit I've spent so much time unlearning but I'm starting to suspect he had a point. My fear of making women uncomfortable is absolutely the primary thing holding me back. It's always what keeps me from starting a conversations, extending a compliment, or even a smile. It's like I just have to accept that my actions will make at least some women uncomfortable some of the time but I just have to do them anyways, or accept being alone. It's fricking bullshit. It's not supposed to work like this, but I've been waiting for women to come up and talk to me for a change for years now and that doesn't work either.