This has been a great thread to read.
From one of the posts: "I'm a shy person. I have no idea how to initiate because I'm never sure. Once that is passed then I'm OK and very active/talkative/being energized."
Let me help with that, for everyone's benefit, a source and then a shortcut.
"How to Win Friends and Influence People" by Dale Carnegie is almost prehistoric, and your goal is survival, not winning friends or getting them to buy your gizmo or gadget. HOWEVER, it has concepts that apply to us in any social situation and deploying them might seem trite and insincere, but if you stop analyzing and just do it, it works out quite well.
A key strategic concept is that most people (most people who aren't just like us) have one favorite topic, and that topic is themselves, and if you get them talking about themselves, what they do, what they like, your conversational burden is negligible, plus they will, in an un-articulated underthought, think you're the greatest person they've ever met for being so interested in their obviously fascinating lives.
Tactically, the book might be dated in terms of culture. I'm not sure how millennials and whatnot go about introducing themselves, but there are two pretty dependable techniques for the average social situation. First, the most obvious common ground with a stranger is the host of whatever event you're attending, and the easiest question is "How long have you known X?" Then you can introduce yourself, and move on to questions to get the person to open up. Second, deliberate introduction, just walk up, stick out your hand, and say "Hi, I'm Bill Watson, and I'm curious about (where you got that tie, what drink you have in your hand, where you met the person you were just talking to, whatever). Most people (of my generation, anyway) are conditioned to respond to an outreached hand. Just don't do it while the person has a drink in one hand and a hamburger in the other. And don't do it when you just visibly came out of the restroom.
Generally stay away from politics and sports until you know the person better.
If you think of the process as gathering information that will let you analyze the person's personality preferences, it might be the spoonful of sugar that makes the medicine go down.
Remember to smile. Yeah, I KNOW there's nothing to smile about, do it anyway.
One fun thing is that you always know when someone else is relying on technique to get by: If someone starts asking you a bunch of questions about you, you can be pretty sure they've read HTWFAIP or one of its many descendants.
The link is to just one site with a free download of the book that seems to have the "concept" thing down pat and also offers proof the book is still widely used. There are other sites that don't want your email.
Hope this helps. The nice thing about the 21st Century is that not only has someone else solved the problem you have, solutions are all at your fingertips.