No, you're supposed to pursue what you want in a gentlemanly and respectful (yet fun and easygoing) manner. If she wants the same, you'll be able to tell, and things will progress.
Yeah, something like that. I know that now. However, most of the unsolicited dating advice I received throughout my life consisted of things like "You're lucky you found a woman that's willing to put up with a piece of shit like you, do what you have to to keep her from breaking up with you," and "that's just how women are, learn to accept it." It took me a while to catch on that those people are ass holes and that that's how insane
women are, not all women. Things are difficult when I don't have any good role models.
I'm sorry that you've had negative experiences in the past (that anecdote about being summoned to a meeting with counselors is indeed pretty terrifying), but there's no simply substitute for confidence (a subject discussed in the Guide
Yes, confidence. Confidence comes from acknowledging that anxiety and self-doubt exist, and working through it. Which is precisely what I'm doing. It kind of sucks when it's happening, but I get through it and then things are awesome. It works much better than pretending my self-doubt isn't there.
The incident in high school, as well as others, while they were terrible at the time, they were experiences that I learned from. Because of them, I'm really good at dealing with bullshit. At this point, there's pretty much nothing someone I'm "dating" can throw at me that I can't handle.
As for the high school girl. A few months later she approached me and explained herself. From her perspective, she thought I was becoming a good friend, but as soon as her boyfriend was out of the way I tried to get into her pants, just like all the other men in her life. She felt betrayed, but later realised that that wasn't what I was doing. It was somewhat understandable, but the damage was done and I couldn't forgive her at the time, although I have since. That was the last time I spoke to her, but at least we parted without completely hating each other.
Just ask her out for a drink/coffee or if you're feeling bold ask her out for dinner.
Try not to come off as sleazy, be respectful and if she says she'd rather not accept it and remain friends.
It really is that easy and it's even easier because you know each other and you don't have to pick up a total stranger. You be amazed how good it feels when you have jumped over yourself in that regard.. no matter the outcome.
Well, yeah, if you want to be all reasonable and level-headed about things.
I also think it's important to have a contingency plan in place so you know what you'll say and how you will act if she clearly rebuffs you. You've already said you're cool about it if she just wants to be friends so really, what do you have to lose?
Not a damn thing, really. Although, I've noticed I seem to be attracted to women who are extremely emotionally unstable. I seem to be moving away from that type, but I've been wrong about that before.
When I ask someone out, what I'm saying is "I like you, and dating seems like a fun idea. What do you think?" but what they seem to hear is "I'm into you, I want you, and I will not give up until I have you." It's kind of understandable, as a lot of men are like that, but it puts a stop to friendship developing. Although, if a woman is determined to make assumptions about me and not listen to anything I have to say that goes against those assumptions, there's really not much I can do.