Here's my take, which is a little less analytical and a little more actionable.
For me, and I'm pretty sure this holds true fo most other people, social awareness is a skill. Meaning that your subconscious brain does it automatically if you have it trained to do it. I know that the times of my life when I'm engaging in people on a regular basis those types of problems go away. However, if I pull myself out of the social world and get really involved in work or personal projects so that I'm just not interacting much and certainly not with a variety of people, then my social interactions get weird. I start to say stupid stuff that doesn't make much sense socially. I'm less confident and sometimes creepy. It's pretty easy to see other people who aren't very social. When they talk to you, it's like they miss the point of the interaction, or they carry on a conversation thread way too long because they have trouble moving onto something new.
I think you need to make a goal of how you want to be and how you want to interact. Then like, ZHereford said, visualize yourself successful in those situations. Then go out into the real world and practice. Just talk to random people you encounter. If you can't encounter enough people (and you probably don't if you're like most shy people) then go looking for people. Hang out at bookstores, or in target, or walk through populated areas and force yourself to initiate short conversations with people. Whenever you come up with a problem that you encounter in a conversation, write it down and then when you're by yourself, write up a plan to avoid that in the future. So if you find that you have trouble getting past small talk, figure out some of the common small talk items you encounter, then create a plan to smoothly transition from those things to something that expresses a little bit about you and allows them to connect with you.
Just remember that being social is a skill and not a trait that you were born with. The more you practice it consciously (or even unconsciously) the better and mroe natural you get at it. If you are unhappy with your social skills, its not a problem with you or something you need to accept. It's just that you didn't practice it enough in the past, so you need to practice it more now to get those skills to where you'd like to be. You need to practice it until your brain does it automatically and you don't have to think about it consciously.
Also maybe it would help if while you are in a conversation, to stop focusing on what you are doing and being weird and focus more on the other person. What are they trying to get out of the conversation? What do they bring up (ie what they want to talk about)? Are they happy? sad? stressed? Also you can focus on what you want out of the conversations? Do you want to get to know them better? Do you want to be able to express who you are to them? Do you want to find common interests and ask them to join you? Do you want to share a beautiful moment with them outside of the hustle and bustle of society ("Do you ever realize that you get so caught up in the busy-ness of every day life and forget to savor how beautiful the world really is? Earlier today, I was walking down the street completely absorbed in all the stuff I had to today, when I felt this warm breeze blow on the back of my neck. As I paid attention to it, I kept feeling the warmth of the sun and the wind hugging me, soothing me, and relaxing me. The more I noticed it, the more it embraced me and the more my tensions melted away. It was like the best massage I've ever gotten.")
Accept that conversations are going to be weird for a little while until you practice enough to be good at it. Focus on what you want and not the weirdness.
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