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It is really HARD to believe that someone that's done 3000 approaches over a decade has NEVER hit pay dirt. "Even a broken clock is right twice a day", so the troll suspicion is understandable.
That's because he HAS hit pay dirt. From the OP:
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But in the Philippines, men are treated like people, and celibacy is recognized as the painful, suffering condition that it is. I actually had sex. Twice! No, scratch that… three times! Two of them were working girls, and one was a girl who I had met on the website.
So two were pros, but one wasn't. Congratulations--you're not a virgin in any sense of the word, either "pro-aided" or on the "fully amateur" level.
Hopefully, assuming you're not a troll, maybe this realization will give you a little bit of peace of mind.
Judging by the rest of your post, I doubt it, so here are a couple more ideas. For the TL;DR crowd, they are:
1) Study comedy a bit, especially improv, and start to figure out what "funny" really is, exactly.
2) Escalate, engage her senses with imagery, and elicit an emotional response. This should increase her attraction in you and get you to the point where she's comfortable/attracted enough for you to seal the deal.
1) You obviously need a little more social awareness/improv ability. Even though you say that cocky-funny helped, I'm not exactly getting "fun-loving, playful, happy-go-lucky guy" off of you. My guess is that there's something "off" about your interactions with chicks that can't really be faked--kinda the same thing ER had going on.
The good news is this is absolutely correctable. If you don't already, I'd recommend watching all of the stand-up specials that you can. My favorites tend to be guys not available on Netflix (Chappelle, Bob Schimmel, etc.), but I think there's at least one Bill Burr special on Netflix, and a few from Jim Jeffries, Louis C.K., and those types of guys.
Watch them. As many as you can. Notice not only the language behind the jokes, but their timing and delivery of them. Figure out the rhythm of humor, common joke constructions, and how to tell an engaging story. All of these skills really, REALLY help when interacting with chicks.
Then pick a couple of comedy podcasts and listen to them while walking around town, working, etc. Two of my favorites are Bill Burr's "Monday Morning Podcast," and "You Made it Weird," with Pete Holmes. Burr is pretty firmly red-pill; Holmes gives off more of a blue pill vibe, but he's incredible with improv (call-backs, "yes-and" agree and escalate, etc.).
Just by osmosis, you'll start to notice that your wit starts to get quicker, you start to recognize joke openings earlier and connect with punchlines more easily. Even studying comedy in this manner can help you shake that "creepy" vibe I assume you're throwing off.
2) The guys earlier in the thread are dead on when they say you need to build attraction. "Attraction," "Escalation," "Desire" when it comes to sales--they're all the same thing: get an emotional response from her. Like anyone else, women "buy" based on their emotions. By increasing this response, you can hook them a lot more quickly and powerfully than you ever thought possible.
There are a bunch of ways to do this--negging is a common one, but one that someone in your situation has to be careful with--the hate just seeps through the screen in your writing, and you might end up lashing out at them for no reason by doing so.
A better option for someone in your situation is probably doing it through imagination and imagery. You want to make the girl associate positive images and thoughts with
you. Engage her senses, get her feeling something with your words--the implication is that you can do "so much more" once you get physical.
It's a little tough to explain how to do this, but I think a good example was when you said you were getting shit for camping out on a rooftop by the ocean. Classic shit test by the girl: "Oh man, you live in a
tent[/]? Lol." To deal with it, you could just give her a sly smile and say something like "Oh yeah, waking up to the sound of waves lapping up on the beach, feeling the sea breeze wash across my face while watching an awesome sunrise is [i]terrible." It's a combination of engaging her senses and agreeing and escalating.
Those are two of A LOT of different things you should be doing. If your inner game is shitty right now, I'd recommend Mark Manson's book, "Models"--it approaches inner game from a different direction, and might be just the thing to get you back on track.
Hopefully, that all helps. Or like I said, at least it's a start.
Vigo