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I can see what you're saying and I can see a few of your more glaring insecurities as well, potentially, one of your boyfriend's. But, in the state that you are now, I don't know how I'd explain it to you without spending hours talking to you.

Instead I'll give you two things that will definitely help you, though you might not understand why at first.

First: you REALLY need to learn how to slow your thoughts down. To analyse your thought patterns and emotions in order to learn how to understand all this by yourself. Look up MINDFULLNESS MEDITATION and practice it. Use it as a tool to calm down this crazy barrage of thoughts and feelings whirling around your head. Use it as a tool to look at your thoughts one by one, feel what emotions those thoughts invoke and better understand how you truly think about things.

Second: Read 7 Habits of Highly Effective People I recommend this book a lot because it really is a great foundation for everything to do with self improvement. The stuff written in that book is exactly the advice I would give to you now plus quite a lot more extremely useful ideas.

The combination of those two things are what got me most of the way to how I am now and they are more than worth your time.

I wish I could just sit here and talk this through with you but... I just don't have the time, sorry :(. Hope I've helped you somewhat and definitely look at the stuff I recommended, they will help you more than you could even comprehend.

The best tip IMO:

Being comfortable by wearing what makes you feel sexy, and having the confidence to rock it! Arden Leigh talks about that in her book. She recommends ridding your wardrobe of things that allow you to feel lazy and frumpy, from old underwear to grubby sweats. Replace it with stuff that makes you feel luxurious and sexy, like night gowns or lacy negligee.

In my experience, this has been so useful. One of the things most men comment on is how feminine I am, which is funny since I'm actually a Tom boy! Mastering the art of seduction is, in part, mastering the art of fashion and beauty. Because lets be honest, our society is pretty image obsessed. We don't all have to look like Dita, but being comfortable with your style doesn't hurt!

You could try posting her pic to one of those online rating sites - it's not an amazing suggestion but it worked for me (as in, I did it for someone else and it really boosted their confidence). A lot about being attractive is confidence and attitude, so work on those first and foremost. I suggest Arden Leigh (http://ardenleigh.typepad.com/) - her blog is very straightforward and honest. http://www.amazon.com/dp/B008PI9RRG her book Isn't bad. Really made me change my attitude to myself.

That is a great tip! I feel like names are something I let fall to the wayside myself.

I read a great post on /r/hntgaf about taking more than 39 seconds to ponder your message so I tried to implement it with a few people I was casually talking with. One person commented "You don't seem like you're lacking in self confidence by the way you speak." I'm usually pretty composed and reserved, so it felt good saying the first thing that came to mind. Obviously, YMMV and don't say some outlandish shit if you're trying to pursue someone.

Also, something that's always worked for me is having an unusual question ready. Play a variant of an ice breaker game, so it doesn't seem so forced. I own The Book of Questions and a few other versions. Don't make it an interview, but having a spontaneous creative question shows you aren't just waiting for them to lead the conversation.

If you're having issues with heels, I'd suggest not wearing the typical stiletto heels everyone thinks of because A) they HURT! and B) you trip all over yourself (if you're as clumsy as I am). I would suggest wearing something of a lace-up wedge like this because it gives you more control of the heel itself AND they don't hurt nearly as much.

If you're worried about towering over guys by wearing heels, just go for a cute studded boot or something to make you feel all badass and sexy.

I haven't finished this book yet, but so far, it looks really good:

https://www.amazon.com/Get-Guy-Learn-Secrets-Deserve/dp/0062241753/ref=sr_1_1?ie=UTF8&qid=1474257235&sr=8-1&keywords=get+the+guy

Give it a try.

Edit: Also, I shot you a PM

New Rules of Attraction: How to Get Him, Keep Him, and Make Him Beg for More

http://www.amazon.com/The-New-Rules-Attraction-Keep/dp/B008PI9RRG/ref=tmm_pap_title_0?ie=UTF8&qid=1368263623&sr=1-1

You sound like a douche. Maybe focus on fixing that first. Might I recommend an etiquette book.