How do I keep from getting stuck in the "acquaintance zone"?

After reading all this, I think that if you spent half the time you do obsessing on things, doing stuff to keep you busy, you’d be a far more interesting person.

I know you’re 16. I get the age and how awkward it is. I don’t get this endless obsessing. I know done of the advice here has been harsh, but it’s been generally spot on.
I would suggest strongly you join the drama or debate clubs. Drama is great because most of the people in the drama club are outgoing, friendly and open to different kinds of people. Debate clubs are great for helping you think on your feet.

As for making conversations, there are tons of self help books out there. I find these are better in audio format because you can hear intimations, etc. Your library (city, not school) will have many, I am sure.

As for a way to talk to girls? Get a study group together. Approach girls in your classes or that have a common connection: “hey aren’t you in Ms. Maxwells class? Do you know what page we’re supposed to read up to?” (Wait for response) “Thanks! I’m going to be starting a study group - you know how insane her exams are. Want to join in?” If she is interested, she’ll say yes, even if she doesn’t need to study for them.

Lastly, I would suggest doing things that will make you a better person. The truth is, and you’ll hate this terribly, but maybe you won’t date someone until college. By doing things such as drama, volunteering to teach the violin to kids once a week, habitat for humanity, etc… You’ll become a better person, you’ll be too busy to obsess, and you’ll have something that will make your college resume stand out. It’s a win-win situation.

Do you plan out one side of all your conversations before they happen? I honestly don’t know what it’s like to be really socially awkward, so maybe thinking about everything you will say is a technique that really helps. Maybe for you it’s better than the alternative.

I can say for certain though that planning everything you intend to say in a conversation isn’t generally a good way to have a pleasant, natural conversation.

What if, when you ask how she’s doing, she says “I’m really stressed. I didn’t study at all for my math test later today.” Are you going to stick to your script and tell her her ass looks amazing in her shorts? You shouldn’t. You should forget about your script entirely and talk about her math class for the 90 seconds you have left to talk before class.

But don’t start planning for that eventuality. I don’t even know this girl. She probably doesn’t even have a math test. She might be really happy because she just got a new puppy. Or really sad because her grandma is in the hospital. Or she might say she’s really relaxed because she ate an amazing pot brownie in homeroom. You just don’t know how she’s doing so you can’t plan the rest of your conversation.

Generally speaking if you are trying to talk to a cute girl for the first time it’s not a good sign if she responds with something like “fine”. It may not have ruined your pre-planned script but she doesn’t seem very interested in talking to you at all. Following up with a compliment, in that case, is going to make you even more boring. You’re better off trying to ask a more interesting question as a last ditch effort to start an actual conversation.

By the way I completely agree with Bad News Baboon that you’re being obsessive and really over-thinking everything. Having a conversation may not come naturally to you, but the way to get better is just practice and stop worrying about it so much.

Yes, it’s fine. That’s how it’s done. Or at least that’s how it was done when I met my wife thirty-some years ago.

And if she says “you ask everybody out” you say, “Nope - only the ones with gorgeous hair” or “a perfect chin” or (better) “who loves book X like I do” or something like that. If you are going to compliment her appearance, do so for something they don’t usually hear. Thus stay away from eyes and smiles (and boobs and butts). Hair is good because women are always doing something or other with their hair and it sounds like you noticed. Tattoos are good too, even though women didn’t have them when I was dating, because everyone wants to tell you the story behind their tattoo. Distinctive jewelry is good too.

90% of succes is just showing up. Just ask, if for no other reason than to get practice going on first dates and getting her to talk about herself.

Regards,
Shodan

Yeah, you are right Fuzzy Dunlop. Once again, thank you all for the advice and verification.

You know what?

I am thinking about just living my life and working towards being happy on my own, getting some friends, etc and instead of trying to look around and see which girls to ask out, to just accept that when the time is right, she will naturally walk into my life.

Other than that, if I develop a crush, I’ll talk to her and see if something happens. If there’s a girl that starts talking to me and showing interest, great. If I by coincidence bump into a girl and we hit it off, great.

But I think I am done trying to chase and actively look for girls. It’s emotionally and mentally draining, even when you haven’t gone on a date.

I’ll just stay true to my dreams and know that when the time is right, life is destined to allow my girl to enter my life.

From what I hear, some people say that doing this is actually more likely to make you run into a COMPATIBLE partner because you’re being yourself and then the girls you attract as a result are attracted to the true you so it all works out and makes sense and is aligned.

What do you think? Is it better to just forget “dating” or trying to “get dates”, live life, and accept that when the time is right, the girl of your dreams will come into your life?

If you can do that, great. I didn’t start until I was 30. It did work, though.

I think going back through the thread at earlier responses would be a good idea. The gist of the vast majority of the responses has been to back off and develop yourself first.

For example, post 3, post 4, post 17, post 46, etc.

Then again, I do understand that it’s sometimes impossible to properly acknowledge advice until we’re personally ready to accept it for what it is instead of what we wish it to be.

Yeah man, I was actually posting a lot on a lot of other forums between these times, even got banned from one, and had some pretty vitriolic discussions, but after taking some time to think things through, this is the consensus I have reached.

Sometimes, I fail to acknowledge advice at first and then come back months later on my own arriving at the same consensus.

Not the first time this has happened.