I was once like you. When I first became "desirable" to women, it was such a sea change that I couldn't really believe it. I would just assume women were being "friendly", or that this is how they treated every guy, and my friends would be rolling their eyes so hard they'd loop around.

Sounds like you've always been desirable, which is a little bit different: you think women behave like this normally. That women randomly sit next to you and strike up conversations. Or invite you to their parties. Or heck, even smile at you for no reason. And I'm here to tell you: NO. Women treat men that they are not interested in, like furniture. They do not even see them, much less interact with them. If they even look at you for more than 5 seconds, it is more of an interaction than they give to 99% of dudes they don't know. Now, this doesn't mean automatically that they will bang you after looking at you (unless you're brad pitt level attractive). But it means they're open to the possibility, if you seal the deal.

It sounds to me like you're terrified of rejection, which is why you do so many things with plausible deniability, sabotaging yourself so that you have an excuse for failure rather than optimizing for success. What do I mean? Lets start.

She sent you a video of her pole dancing. Do you think she does this to every guy? Of course not. She wanted you. At that time she was dating someone else so you stayed away. Good for you. Except you really didn't stay away. You spent hours in conversation with her. Like a nice, chaste blue pill beta. Why? I don't mean you can't have female friends. But it's clear you've wanted to fuck this one since you were 14. Why are you being her nice guy friend? Do the hours of redpill videos you watch tell you to do this?

What you should have done, when she sent you that video, is file her away in your mind as someone interested in hopping on your dick, but not one worthy of a relationship (since she's sending you this stuff while dating someone else). And decide if you want to use her recreationally. If yes, fine. And accept that that might mean upsetting her family, getting a reputation around town, whatever. Or if those costs are too high, then decide no. Either decision is fine. The key is not to vacillate between the two. Decide what you're going to do, and do it and don't half ass it.

It is clear you decided you'd like to fuck her, though you didn't want to commit fully to that because of the fear of rejection. So you tried the nice guy game. No women is going to reject a guy offering a shoulder to cry on. So much easier to offer that. Even if it reduces your chances of fucking her later. Mistake #1.

At any rate, she breaks up with her guy. You're all on a boat. And you invite her family to come to your pool. Bullshit. You wanted her to come hang out with you. But instead of telling her directly, you told her whole family. So that you could have plausible deniability that, no, I'm not really trying to get in your pants, I just genuinely wanted you and your family to come hang out at my pool! What you should have done, is tell her to come by your pool. Make it clear it would just be you two. Throw in some sexual banter if you'd like. Make it clear what you intend, which is not to just have her come over so you can host her and clean up the pool afterwards. Take the risk that she'll decline if she's not interested. You'll come to realize this is a blessing in disguise: better to take the rejection early rather than waste a bunch of time when you're not sure.

Despite that, she calls you and wants to hang out. Here's where an underappreciated consideration comes into play: logistics. That day, you have a bunch of cold sores and are sunburned, and are in no mood for sexy time. Then why did you allow her to come? Even if it's last minute, cancel. Come up with a reason and reschedule. Because why waste your time with this if you know the logistics makes it impossible that anything will happen? Do you buy tickets to a basketball game on a night you know you can't attend? So that you can give them away to a friend? Because that's what you did: you had her come over, get all hot and bothered in her bikini, and handed her on a silver platter to the first guy she matched on tinder. I'm sure that army dude thanks you for the free ticket you bought him.

So ask yourself: why did you invite her, knowing you couldn't fuck her that day? And I think the reason is, you reassured yourself that she wouldn't fuck you anyway, and you guys were just hanging out. IOW, you rejected yourself before she could do it to you. Much easier on the ego.

So anyway, you try again later. Again with the excuses: this time you're really tired from work and came home late. Perhaps if you're already in a relationship with this girl, you can come home late and tired and still climb into bed and fuck. But if it's a new girl, why handicap yourself with such poor logistics? You know you'll need time and energy to flirt with her and escalate. So invite her on a day you know will be light, maybe even on a weekend or a day off.

But regardless, you come home already drained. Carrying on a fun, flirtatious energy would be hard, but even worse she's started the shit tests and the jealousy game. She gave you a few hours to pull her bikini off and take her to the bedroom and you didn't make a move, so she starts insulting you. And again, you can't decide if you want to go for it, risking rejection, or just sit there and take it. Let me ask you, if you had no interest in this girl, would you have taken it? Of course not. You wouldn't have even invited her to you house in the first place, and would have thrown her out if she started doing this. But you do still want to fuck this one, so you don't want to throw her out and risk closing the door permanently on that possibility, and so you sit there and take it from her, even though redpill teaches you that not setting boundaries is the way to close that door.

So now she's not sure what to think. You didn't get upset. You didn't get turned on (maybe she though you had a cuck fetish?). You didn't end the night, or even the conversation as she's going into graphic detail. You didn't make a move. You just.... Existed. Until finally she finally passed out drunk waiting for you to do something. Which you didn't do because you were paralyzed that you might mess up your "chance".

So in summary, you violated a number of red pill rules. But the biggest is outcome independence. Do not give a shit if you get rejected. If you want something from a girl, take the shot. If she declines, move on. Don't pussyfoot for months because you're afraid.

The second most important is to learn to read women's signals. Like I said, women do not talk to strange men for no reason. And they certainly don't grab you and take pictures for their Instagram with you. And yes, in those situations there's still a small chance you'll botch it, but didn't let that risk stand in the way of going for it.

Maybe here, you're worried about pissing off her family, but what was the reason not to fuck that cougar you mentioned? Even if she rejected you, so what? You'll never see her again. You have to get rid of this fear of rejection. Realize that when a woman rejects you, it can be for a hundred reasons, only one of which is that you genuinely suck as a human being. Far more commonly, it's because you're simply not her type, or she's already seeing someone one, she's not in the mood to be fucked that night, her friends will slut shame her, or whatever. So understand that a rejection is very rarely a reflection on you. At best, it might be a reflection on your technique, but not your worth as a human being, which you should never let a woman define for you anyway.

Anyway, hope this is helpful. The good news is, it seems you have no problem attracting hot women. That's the biggest hurdle. The rest is getting your head straight about the [lack of consequences] of rejection.